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1. Diversifying top-k Answers in a Query by Example Setting

Author

Smits, Grégory, Lesot, Marie-Jeanne, Pivert, Olivier, Reformat, Marek, Département Informatique (IMT Atlantique - INFO), IMT Atlantique (IMT Atlantique), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT), Laboratoire des sciences et techniques de l'information, de la communication et de la connaissance (Lab-STICC), École Nationale d'Ingénieurs de Brest (ENIB)-Université de Bretagne Sud (UBS)-Université de Brest (UBO)-École Nationale Supérieure de Techniques Avancées Bretagne (ENSTA Bretagne)-Institut Mines-Télécom [Paris] (IMT)-Centre National de la Recherche Scientifique (CNRS)-Université Bretagne Loire (UBL)-IMT Atlantique (IMT Atlantique), Institut Mines-Télécom [Paris] (IMT), Equipe MOTEL (Lab-STICC_MOTEL), Institut Mines-Télécom [Paris] (IMT)-École Nationale d'Ingénieurs de Brest (ENIB)-Université de Bretagne Sud (UBS)-Université de Brest (UBO)-École Nationale Supérieure de Techniques Avancées Bretagne (ENSTA Bretagne)-Institut Mines-Télécom [Paris] (IMT)-Centre National de la Recherche Scientifique (CNRS)-Université Bretagne Loire (UBL)-IMT Atlantique (IMT Atlantique), Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-IMT Atlantique (IMT Atlantique), and University of Alberta

Subjects
diversified top-k answers, [INFO.INFO-DB]Computer Science [cs]/Databases [cs.DB], Querying by example
Abstract

International audience; For a given data base T and a user query Q, the top-k answers are the k tuples from T that best match Q. The integration of a diversity constraint aims at avoiding returning redundant tuples, that are too similar one to another. This paper addresses the diversification question in the Query By Example setting, especially for approaches that can deal with possibly very different representative examples provided by the user. It proposes a new definition for diversity that depends on the query, in order to guarantee that the result set illustrates the diversity of the representative examples provided by the user, covering all components of the query. The paper proposes a numerical measure to assess diversity in that sense, an algorithm to identify such a diversified top-k set, optimising both the query satisfaction and the diversity measure, as well as its integration into a flexible querying approach.

Published
2023

2. Vers un partitionnement des données à partir d'une forêt d'isolation

Author

Yepmo, Véronne, Smits, Grégory, Lesot, Marie-Jeanne, Pivert, Olivier, Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-IMT Atlantique (IMT Atlantique), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT), IMT Atlantique (IMT Atlantique), Institut Mines-Télécom [Paris] (IMT), Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Projet SEA DEFENDER - Direction Générale de l'Armement, and Association EGC

Subjects
explication d'anomalies, [INFO]Computer Science [cs], détection d'anomalies, forêt d'isolation, clustering
Abstract

National audience; This paper takes a step towards the extraction of contrastive explanations between anoma- lies and the intrinsic structure of regular points. It proposes a variant of the isolation forest algorithm whose main objective is to preserve the structure of regular data in order to facilitate its reconstruction. Experiments conducted on synthetic datasets show that this variant of isola- tion forest deteriorates less the structure of regular data than the classical method. Therefore, the former can serve as a basis for a unified approach to anomaly detection and explanation.; Cet article effectue un pas vers une extraction d'explications contrastives entre anomalies et structure intrinsèque des points réguliers. Il propose une variante de l'algorithme des forêts d'isolation ayant pour objectif principal la préservation de la structure des données régulières en vue de sa reconstitution plus aisée. Les expérimentations menées sur des jeux de données synthétiques montrent que cette variante des forêts d'isolation détériore moins la structure des données régulières que la méthode classique. Par conséquent, la première citée peut servir de base pour une approche unifiée de détection et d'explication d'anomalies.

Published
2023

3. Exploration de données massives à l'aide d'estimations de cardinalités

Author

Nerzic, Pierre, Smits, Grégory, Pivert, Olivier, Lesot, Marie-Jeanne, A Symbolic and Human-centric view of dAta MANagement (SHAMAN), GESTION DES DONNÉES ET DE LA CONNAISSANCE (IRISA-D7), Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-IMT Atlantique (IMT Atlantique), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT), Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Ce travail s’inscrit dans le cadre du projet SEA Defender financé par la Direction Générale de l’Armement, and SMITS, Grégory

Subjects
estimation de cardinalités, [INFO.INFO-DB]Computer Science [cs]/Databases [cs.DB], big data, [INFO.INFO-IR]Computer Science [cs]/Information Retrieval [cs.IR], [INFO.INFO-DB] Computer Science [cs]/Databases [cs.DB], linguistic summarization, [INFO.INFO-IR] Computer Science [cs]/Information Retrieval [cs.IR], vocabulary inference, inférence de vocabulaire, cardinality estimation, résumés linguistiques, données massives
Abstract

This paper describes FuzViz, a tool to explore interactively massive relational data. FuzViz relies on a method building automatically linguistic summaries, that provide concise and intelligible insights in the data content. It offers an interactive view of these summaries, dynamically recomputed on demand. To ensure a fluid exploration of the data, FuzViz exploits the proposition of a highly efficient method for estimating the cardinality ofthe summary properties, estimated from statistics about the data distribution stored in the relational data base, consolidated by a sampling-based approach. The proposed workflow also involves a vocabulary inference mechanism from these statistics., Cet article présente un outil d'exploration interactive de données massives stockées dans un système de gestion de base de données (SGBD), nommé FuzViz. Il repose sur une méthode de construction automatique de résumés linguistiques, qui fournissent une synthèse concise et intelligible du contenu des données. Il offre une vue interactive de ces résumés recalculée dynamiquement selon les demandes de l'utilisateur. Pour assurer une exploration fluide des propriétés décrites par ces résumés, FuzViz s'appuie sur la proposition d'une méthode efficace d'estimations de leurs cardinalités, produites à partir des statistiques sur la distribution des données gérées par le SGBD et consolidées par une approche basée sur un échantillonnage. L'outil propose de plus un mécanisme d'inférence de vocabulaire flou à partir de ces statistiques.

Published
2022

4. PANDA : Personnaliser les ANomalies Détectées par Apprentissage

Author

Smits, Grégory, Lesot, Marie-Jeanne, Yepmo, Véronne, Pivert, Olivier, A Symbolic and Human-centric view of dAta MANagement (SHAMAN), GESTION DES DONNÉES ET DE LA CONNAISSANCE (IRISA-D7), Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-IMT Atlantique (IMT Atlantique), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT), Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR), and SMITS, Grégory

Subjects
[INFO.INFO-DB]Computer Science [cs]/Databases [cs.DB], [INFO.INFO-IR]Computer Science [cs]/Information Retrieval [cs.IR], vocabulaire flou, fuzzy vocabulary, linguistic description, détection et explication d'anomalies, [INFO.INFO-DB] Computer Science [cs]/Databases [cs.DB], outlier explanation, [INFO.INFO-IR] Computer Science [cs]/Information Retrieval [cs.IR], outlier detection, human-in-the-loop, description linguistique, approche orientée utilisateur
Abstract

The paper addresses the tasks of anomaly detection and explanation simultaneously, in the human-in-the-loop paradigm integrating the end-user expertise : it first proposes to exploit two complementary data representations to identify anomalies, namely the description induced by the raw features and the description induced by a userdefined vocabulary. These representations respectively lead to identify so-called data-driven and knowledge driven anomalies. The paper then proposes to confront these two sets of instances so as to improve the detection step and to dispose of tools towards anomaly explanations. It distinguishes and discusses three cases, underlining how the two description spaces can benefit from oneanother, in terms of accuracy and interpretability., La personnalisation par prise en compte de l'expertise de l'utilisateur des processus de détection d'anomalies est le sujet principal de cet article. Les anomalies sont identifiées dans deux espaces de représentation des données, l'espace initial composé des valeurs brutes et l'espace induit par un vocabulaire flou défini par l'utilisateur sur ces attributs initiaux. L'application de toute méthode de détection d'anomalies sur ces deux espaces conduit à différencier des anomalies issues des données brutes de celles issues du vocabulaire. Afin à la fois d'améliorer la détection des exceptions et de disposer d'outils pour les expliquer, ces deux ensembles d'anomalies sont confrontés. Trois situations émanant de cette comparaison sont étudiées afin de montrer comment l'utilisation combinée des deux espaces améliore l'efficacité de la procédure de détection d'anomalies ainsi que l'interprétabilité des résultats qu'elle génère.

Published
2022

5. CoAT-APC: When Analogical Proportion-based Classification Meets Case-based Prediction

Author

Fadi Badra, Marie-Jeanne Lesot, Laboratoire d'Informatique Médicale et Ingénierie des Connaissances en e-Santé (LIMICS), Université Paris 13 (UP13)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Sorbonne Université (SU), Learning, Fuzzy and Intelligent systems (LFI), Laboratoire d'Informatique de Paris 6 (LIP6), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Badra, Fadi

Subjects
[INFO.INFO-AI] Computer Science [cs]/Artificial Intelligence [cs.AI], case-based prediction, analogical proportion-based classification, interactions between case-based and analogical reasoning, [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

International audience; This paper proposes to view analogical proportion-based classification as a special type of case-based prediction algorithm, in which (i) cases are differences between two instances, and (ii) only maximally similar cases are compared. It then proposes to tweak the CoAT case-based prediction algorithm in order to implement these two key design principles. The resulting analogical proportion-based classifier CoAT-APC shows a performance comparable to state-of-the-art analogical proportion-based classifiers, while implementing a different transfer strategy, based on the minimization of a dataset complexity measure, as opposed to a rule-based approach. Experimental results show the usefulness of combining these two design principles and suggest that the rule-based transfer strategy of analogical proportionbased classifiers has comparatively little impact on the performance of the system.

Published
2022

6. PANDA: Human-in-the-Loop Anomaly Detection and Explanation

Author

Smits, Grégory, Lesot, Marie-Jeanne, Tchaghe, Véronne, Pivert, Olivier, Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-IMT Atlantique (IMT Atlantique), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT), A Symbolic and Human-centric view of dAta MANagement (SHAMAN), GESTION DES DONNÉES ET DE LA CONNAISSANCE (IRISA-D7), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)-Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Learning, Fuzzy and Intelligent systems (LFI), LIP6, and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[INFO.INFO-DB]Computer Science [cs]/Databases [cs.DB], XAI, human-in-theloop, [INFO.INFO-IR]Computer Science [cs]/Information Retrieval [cs.IR], fuzzy vocabulary, linguistic description, outlier explanation, outlier detection
Abstract

International audience; The paper addresses the tasks of anomaly detection and explanation simultaneously, in the human-in-the-loop paradigm integrating the end-user expertise: it first proposes to exploit two complementary data representations to identify anomalies, namely the description induced by the raw features and the description induced by a user-defined vocabulary. These representations respectively lead to identify so-called data-driven and knowledge-driven anomalies. The paper then proposes to confront these two sets of instances so as to improve the detection step and to dispose of tools towards anomaly explanations. It distinguishes and discusses three cases, underlining how the two description spaces can benefit from one another, in terms of accuracy and interpretability.

Published
2022

7. De l’équivalence entre les modèles structurels causaux et les systèmes abstraits d’argumentation

Author

Munro, Yann, Bloch, Isabelle, Chetouani, Mohamed, Lesot, Marie-Jeanne, Pelachaud, Catherine, and Munro, Yann

Subjects
[INFO.INFO-AI] Computer Science [cs]/Artificial Intelligence [cs.AI], Modèles structurels causaux, Explications en intelligence artificielle (XAI), Systèmes abstraits d'argumentation
Abstract

Les modèles structurels causaux et les systèmes abstraits d'argumentation sont deux approches s'inscrivant dans les problématiques de l'intelligence artificielle explicable. Dans cet article, nous mettons en évidence une équivalence entre un cas particulier de ces modèles causaux, que nous appelons graphes causaux argumentatifs, et les systèmes abstraits d'argumentation. Nous proposons également une transformation permettant de passer d'une représentation à l'autre.

Published
2022

9. Fuzzy Conceptual Graphs: a comparative discussion

Author

Adam Faci, Marie-Jeanne Lesot, Claire Laudy, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Thales Research and Technologies [Orsay] (TRT), and THALES

Subjects
FOS: Computer and information sciences, Computer Science - Logic in Computer Science, Logique floue, Computer Science - Artificial Intelligence, Computer Science - Information Theory, Information Theory (cs.IT), [INFO.INFO-DS]Computer Science [cs]/Data Structures and Algorithms [cs.DS], [INFO.INFO-LO]Computer Science [cs]/Logic in Computer Science [cs.LO], Knowledge Representation, Logic in Computer Science (cs.LO), Artificial Intelligence (cs.AI), Fuzzy Logic, [INFO.INFO-IT]Computer Science [cs]/Information Theory [cs.IT], Conceptual Graphs, Représentation de la connaissance, Graphes conceptuels
Abstract

International audience; Conceptual Graphs (CG) are a graph-based knowledge representation and reasoning formalism; fuzzy Conceptual Graphs (fCG) constitute an extension that enriches their expressiveness, exploiting the fuzzy set theory so as to relax their constraints at various levels. This paper proposes a comparative study of existing approaches over their respective advantages and possible limitations. The discussion revolves around three axes: (a) Critical view of each approach and comparison with previous propositions from the state of the art; (b) Presentation of the many possible interpretations of each definition to illustrate its potential and its limits; (c) Clarification of the part of CG impacted by the definition as well as the relaxed constraint.; Les Graphes Conceptuels (GC) sont un formalisme de représentation de la connaissance et de raisonnement basé sur les graphes. Les Graphes Conceptuels flous (GCf) constituent une extension qui enrichit leur expressivité, en exploitant la théorie des ensembles flous de manière à relâcher leurs contraintes à différents niveaux. Cet article propose une étude comparative des approches existantes sur leurs avantages respectifs et leurs éventuelles limitations. La discussion s'articule autour de trois axes: (a) Vue critique de chaque approche et comparaison avec les propositions précédentes de l'état de l'art; (b) Présentation des interprétations possibles de chaque définition pour illustrer son potentiel et ses limites; (c) Clarification de la partie des GC impactée par la définition ainsi que la contrainte relâchée.

Published
2021

10. Vers une formulation floue des explications par contraste

Author

Bloch, Isabelle, Lesot, Marie-Jeanne, Laboratoire Traitement et Communication de l'Information (LTCI), Institut Mines-Télécom [Paris] (IMT)-Télécom Paris, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Image, Modélisation, Analyse, GEométrie, Synthèse (IMAGES), Institut Mines-Télécom [Paris] (IMT)-Télécom Paris-Institut Mines-Télécom [Paris] (IMT)-Télécom Paris, Département Images, Données, Signal (IDS), Télécom ParisTech, and Bloch, Isabelle

Subjects
[INFO]Computer Science [cs], [INFO] Computer Science [cs], ComputingMilieux_MISCELLANEOUS
Abstract

National audience

Published
2021

11. Exploring the enantiomeric 13C position-specific isotope fractionation: challenges and anisotropic NMR-based analytical strategy

Author

Virginie Silvestre, P. Berdagué, Gérald S. Remaud, Philippe Lesot, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université Paris-Saclay, Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN), and ISOTOP 2018-2019 grant) from CNRS

Subjects
13C-{1H} NMR, Polypeptide liquid crystals, 010405 organic chemistry, Chemistry, Carbon-13, Context (language use), 13C-RCSA, 010402 general chemistry, 01 natural sciences, Biochemistry, 0104 chemical sciences, Analytical Chemistry, Residual chemical shift anisotropy, Enantiopure drug, Isotope fractionation, Liquid crystal, Computational chemistry, (13C/12C) ratio, Enantiomeric isotopic fractionation, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Homochirality, Enantiomer, Chirality
Abstract

International audience; Trying to answer the intriguing and fundamental question related to chiral induction/amplification at the origin of homochirality in Nature: "Is there a relationship between enantiomeric and isotopic fractionation of carbon 13 in chiral molecules?" is a difficult but stimulating challenge. Although isotropic 13C-PSIA NMR is a promising tool for determination of (13C/12C) ratios capable of providing key 13C isotopic data for understanding the reaction mechanisms of biological processes or artificial transformations, this method does not provide access to any enantiomeric 13C isotopic data unless mirror-image isomers are first physically separated. Interestingly, 13C spectral enantiodiscriminations can be potentially performed in situ in presence of enantiopure entities as chiral-europium complexes or chiral liquid crystals (CLCs). In this work, we explored for the first time the capabilities of the anisotropic 13C-{1H} NMR using PBLG-based lyotropic CLCs as enantiodiscriminating media in the context of the enantiomeric position-specific 13C isotope fractionation (EPSIF), within the requested precision of the order of the permil. As enantiomeric NMR signals are discriminated on the basis of a difference of 13C residual chemical shift anisotropy (13C-RCSA) prior to be deconvoluted, analysis of enantiomeric mixtures becomes possible. The analytical potential of this approach when using poly--benzyl-L-glutamate (PBLG) is presented, and the preliminary quantitative results on small model chiral molecules obtained at 17.5 T with a cryogenic NMR probe are reported and discussed

Published
2021
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12. CG2A: Conceptual Graphs Generation Algorithm

Author

Marie-Jeanne Lesot, Adam Faci, Claire Laudy, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Thales Research and Technologies [Orsay] (TRT), and THALES

Subjects
FOS: Computer and information sciences, Vocabulary, [INFO.INFO-DB]Computer Science [cs]/Databases [cs.DB], Formalism (philosophy), Computer science, Test data generation, media_common.quotation_subject, [INFO.INFO-DS]Computer Science [cs]/Data Structures and Algorithms [cs.DS], Databases (cs.DB), Predictability, [INFO.INFO-MO]Computer Science [cs]/Modeling and Simulation, Set (abstract data type), Ontological knowledge, Computer Science - Databases, Conceptual graph, ComputingMethodologies_SYMBOLICANDALGEBRAICMANIPULATION, Conceptual Graphs, Data generation, Variability, Algorithm, media_common
Abstract

International audience; Conceptual Graphs (CGs) are a formalism to represent knowledge. However producing a CG database is complex. To the best of our knowledge, existing methods do not fully use the expressivity of CGs. It is particularly troublesome as it is necessary to have CG databases to test and validate algorithms running on CGs. This paper proposes CG2A, an algorithm to build synthetic CGs exploiting most of their expressivity. CG2A takes as input constraints that constitute ontological knowledge including a vocabulary and a set of CGs with some label variables, called γ-CGs, as components of the generated CGs. Extensions also enable the automatic generation of the set of γ-CGs and vocabulary to ease the database generation and increase variability.; Les graphes conceptuels (GC) sont un formalisme permettant de représenter les connaissances. Cependant, la production d'une base de données de GC est complexe. À notre connaissance, les méthodes existantes n'utilisent pas pleinement l'expressivité des GC. Cela est particulièrement gênant car il est nécessaire de disposer de bases de données de GC pour tester et valider les algorithmes fonctionnant sur les GC. Cet article propose CG2A, un algorithme permettant de construire des GC synthétiques en exploitant au maximum leur expressivité. CG2A prend en entrée des contraintes qui constituent des connaissances ontologiques, comprenant un vocabulaire et un ensemble de GC particuliers incluant des variables, appelées GC-γ, comme composants des GC générés. Des extensions permettent également la génération automatique de l'ensemble des GC-γ et du vocabulaire pour faciliter la génération de la base de données et augmenter la variabilité.

Published
2021
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13. Fuzzy Approaches for Soft Computing and Approximate Reasoning: Theories and Applications: Dedicated to Bernadette Bouchon-Meunier

Author

Lesot, Marie-Jeanne, Marsala, Christophe, Learning, Fuzzy and Intelligent systems (LFI), LIP6, and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

International audience; This book gathers cutting-edge papers in the area of Computational Intelligence, presented by specialists, and covering all major trends in the research community in order to provide readers with a rich primer. It presents an overview of various soft computing topics and approximate reasoning-based approaches, both from theoretical and applied perspectives. Numerous topics are covered: fundamentals aspects of fuzzy sets theory, reasoning approaches (interpolative, analogical, similarity-based), decision and optimization theory, fuzzy databases, soft machine learning, summarization, interpretability and XAI. Moreover, several application-based papers are included, e.g. on image processing, semantic web and intelligent tutoring systems. This book is dedicated to Bernadette Bouchon-Meunier in honor of her achievements in Computational Intelligence, which, throughout her career, have included profuse and diverse collaborations, both thematically and geographically.

Published
2021
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14. XAI: a Natural Application Domain for Fuzzy Set Theory

Author

Bouchon-Meunier, Bernadette, Laurent, Anne, Lesot, Marie-Jeanne, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), and Alice E. Smith

Subjects
MESH: Fuzzy logic, Artificial Intelligence, Explainable AI (XAI), Computing With Words, Machine Learning, Approximate Reasoning, ComputingMilieux_MISCELLANEOUS, [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

International audience

Published
2021

15. Lotfi A. Zadeh, the visionary in Explainable Artificial Intelligence

Author

Bouchon-Meunier, Bernadette, Lesot, Marie-Jeanne, Marsala, Christophe, Bouchon-Meunier, Bernadette, Learning, Fuzzy and Intelligent systems (LFI), LIP6, and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
ACM: I.: Computing Methodologies/I.2: ARTIFICIAL INTELLIGENCE, fuzzy sets, [INFO.INFO-AI] Computer Science [cs]/Artificial Intelligence [cs.AI], knowledge represen-tation, artificial intelligence, eXplainable artificial intelligence (XAI), [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI], Lotfi A. Zadeh
Abstract

International audience; In this paper, we describe various aspects of Explainable Artificial Intelligence (XAI) and we show that fuzzy systems can help to approach several of these aspects. We focus on the pioneering works of L. A. Zadeh that offer precious tools for the current XAI challenges. We show that they are not limited to approaches of natural language, but they also help to assist the user in understanding the meaning of the decisions made by artificial intelligence-based systems and to provide explanations about the way these decisions are made.

Published
2021

16. Logique pour l'informatique

Author

Jaume, Mathieu, Journault, Matthieu, Lesot, Marie-Jeanne, Manoury, Pascal, Mounier, Isabelle, Modélisation et Vérification (MoVe), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Algorithmes, Programmes et Résolution (APR), Laboratoire d'Informatique de Paris 6 (LIP6), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Learning, Fuzzy and Intelligent systems (LFI), and Jaume, Mathieu

Subjects
ACM: F.: Theory of Computation/F.4: MATHEMATICAL LOGIC AND FORMAL LANGUAGES, Logique, ACM: F.: Theory of Computation/F.3: LOGICS AND MEANINGS OF PROGRAMS, [INFO.INFO-LO] Computer Science [cs]/Logic in Computer Science [cs.LO], [INFO.INFO-LO]Computer Science [cs]/Logic in Computer Science [cs.LO], [INFO]Computer Science [cs], [INFO] Computer Science [cs]
Abstract

National audience; Cet ouvrage débute par une introduction à la logique des prédicats du premier ordre : syntaxe, sémantique et preuves formelles. Il guide ensuite le lecteur vers quelques uns de ses aspects plus avancés : théorème de complétude, théorème d'indécidabilité. Se tournant ensuite vers les rapports de la logique et de l'informatique, il présente les méthodes algorithmiques de démonstration automatique comme la résolution et l'unification ainsi que des applications plus directes des concepts logiques au domaine informatique (problème SAT, bases de données relationnelles, vérification de modèle, etc.)Sa lecture ne demande aucun prérequis en la matière et peut s'adresser à tout étudiant débutant en logique (licence ou master d'informatique, élève ingénieur). L'exposé des notions de base de logique sont accompagnées de nombreux exercices corrigés.

Published
2020

17. Subspace clustering et degrés de typicité d'attributs : une étude prospective

Author

Lesot, Marie-Jeanne, Revault d'Allonnes, Adrien, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Laboratoire d'Informatique Avancée de Saint-Denis (LIASD), Université Paris 8 Vincennes-Saint-Denis (UP8), and Revault d'Allonnes, Adrien

Subjects
[INFO.INFO-AI] Computer Science [cs]/Artificial Intelligence [cs.AI], [INFO.INFO-LG]Computer Science [cs]/Machine Learning [cs.LG], [INFO]Computer Science [cs], [INFO.INFO-LG] Computer Science [cs]/Machine Learning [cs.LG], [INFO] Computer Science [cs], [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

Subspace clustering can offer, beside a decomposition of data into homogeneous and distinct clusters, a characterisation of the subspaces in which the clusters live. This paper explores the possibility of capturing the notion of characteristic features in the framework of typicality degrees , as typical features. To that aim, it discusses the notion of typicality degrees for features and proposes an Alternating Cluster Estimation algorithm, named TbSC, to exploit these degrees within subspace clustering. It illustrates their differences experimentally using simple data sets., Au-delà de la décomposition de données en clusters homogènes et distincts, le subspace-clustering peut proposer une caractérisation des sous-espaces dans lesquels les clusters vivent. Cet article propose d'étudier la possibilité de capturer la notion d'attribut caractéristique dans le cadre des degrés de typicité, comme attribut ty-pique. Dans ce but, il étudie la notion de degrés de typicité pour les attributs et propose un algorithme d'estimation alternée de clusters, nommé TbSC, afin d'exploiter ces degrés dans le subspace clustering. Il illustre leurs différences sur des bases de données simples.

Published
2020

18. Subspace Clustering and Feature Typicality Degrees: a Prospective Study

Author

Adrien Revault d'Allonnes, Marie-Jeanne Lesot, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Laboratoire d'Informatique Avancée de Saint-Denis (LIASD), and Université Paris 8 Vincennes-Saint-Denis (UP8)

Subjects
Computer science, business.industry, Pattern recognition, 02 engineering and technology, 010501 environmental sciences, 01 natural sciences, Linear subspace, [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI], Data set, ComputingMethodologies_PATTERNRECOGNITION, Subspace clustering, Simple (abstract algebra), 0202 electrical engineering, electronic engineering, information engineering, Feature (machine learning), 020201 artificial intelligence & image processing, [INFO]Computer Science [cs], Artificial intelligence, business, 0105 earth and related environmental sciences
Abstract

International audience; Subspace clustering can offer, beside a decomposition of data into homogeneous and distinct clusters, a charac-terisation of the subspaces in which the clusters live. This paper explores the possibility of capturing the notion of characteristic features in the framework of typicality degrees, as typical features. To that aim, it discusses the notion of typicality degrees for features and proposes an Alternating Cluster Estimation algorithm, named TbSC, to exploit these degrees within subspace clustering. It illustrates their differences experimentally using simple data sets.

Published
2020
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19. 2H QUOSY 2D-NMR Experiments in Weakly Aligning Systems: From the Conventional to the UF Approach

Author

Abdelkrim Meddour, Boris Gouilleux, Philippe Lesot, Université Paris-Saclay, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS), and Financement récurrent du CNRS et de l'Université PAris-Sud/ Paris-Saclay

Subjects
Materials science, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Molecular physics, Homonuclear molecule, Spectral line, Liquid crystal, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Quadrupolar splitting, Physical and Theoretical Chemistry, Spectroscopy, QUOSY, Chemical shift, 021001 nanoscience & nanotechnology, Deuterium, Atomic and Molecular Physics, and Optics, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Ultrafast, 0210 nano-technology, 2D-NMR, Ultrashort pulse, Two-dimensional nuclear magnetic resonance spectroscopy, Aligning media
Abstract

We describe three anisotropic ultrafast (UF) QUadrupolar Ordered SpectroscopY (QUOSY) 2D-NMR experiments (referred to as ADUF 2D NMR spectroscopy) designed for recording the 2 H homonuclear 2D spectra of weakly aligned (deuterated) solutes in sub-second experiment times. These new ADUF 2D experiments derive from the Q-COSY, Q-resolved and Q-DQ 2D pulse sequences (J. Am. Chem. Soc. 1999, 121, 5249) and allow the correlation between the two components of each quadrupolar doublet, and then their assignment on the basis of 2 H chemical shifts. The UF 2D pulse sequences are analyzed by using the Cartesian spin-operator formalism for spin I=1 nuclei with a small quadrupolar moment. The optimal experimental/practical conditions as well as the resolution, sensitivity and quantification issues of these ADUF 2D experiments are discussed on comparison to their conventional 2D counterparts and their analytical potentialities. Illustrative ADUF 2D experiments using deuterated achiral/prochiral/chiral solutes in poly-γ-benzyl-L-glutamate based chiral liquid crystals are presented, as well as the first examples of natural abundance deuterium (ANADUF) 2D spectrum using 14.1 T magnetic field and a basic gradient unit (53 G.cm-1 ) in oriented solvents.

Published
2020
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20. Concept Membership Modeling Using a Choquet Integral

Author

Olivier Pivert, Ronald R. Yager, Marie-Jeanne Lesot, Grégory Smits, Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-IMT Atlantique (IMT Atlantique), and Institut Mines-Télécom [Paris] (IMT)-Institut Mines-Télécom [Paris] (IMT)

Subjects
Property (philosophy), Information retrieval, [INFO.INFO-DB]Computer Science [cs]/Databases [cs.DB], Computer science, media_common.quotation_subject, Aggregate (data warehouse), 020207 software engineering, 02 engineering and technology, Data point, Choquet integral, [INFO.INFO-IR]Computer Science [cs]/Information Retrieval [cs.IR], 0202 electrical engineering, electronic engineering, information engineering, Fuzzy concept, 020201 artificial intelligence & image processing, Relevance (information retrieval), Function (engineering), Membership function, ComputingMilieux_MISCELLANEOUS, media_common
Abstract

Imprecise and subjective concepts, as e.g. promising students, may be used within data mining tasks or database queries to faithfully describe data properties of interest. However, defining these concepts is a demanding task for the end-user. We thus provide a strategy, called CHOCOLATE, that only requires the user to give a tiny subset of data points that are representative of the concept he/she has in mind, and that infers a membership function from them. This function may then be used to retrieve, from the whole dataset, a ranked list of points that satisfy the concept of interest. CHOCOLATE relies on a Choquet integral to aggregate the relevance of individual attribute values among all the representative points as well as the representativity of sets of such attribute values. As a consequence, a valuable property of the proposed approach is that it is able to both capture properties shared by most of the user-selected representative data points as well as specific properties possessed by only one specific representative data point.

Published
2020
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21. Information Processing and Management of Uncertainty in Knowledge-Based Systems: 18th International Conference, IPMU 2020, Lisbon, Portugal, June 15-19, 2020, Proceedings, Part II

Author

Lesot, Marie-Jeanne, Vieira, Susana, Reformat, Marek, Carvalho, João Paulo, Wilbik, Anna, Bouchon-Meunier, Bernadette, Yager, Ronald, Learning, Fuzzy and Intelligent systems (LFI), LIP6, and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
ComputingMilieux_MISCELLANEOUS, [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

International audience

Published
2020
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22. Information Processing and Management of Uncertainty in Knowledge-Based Systems: 18th International Conference, IPMU 2020, Lisbon, Portugal, June 15-19, 2020, Proceedings, Part III

Author

Lesot, Marie-Jeanne, Vieira, Susana, Reformat, Marek, Carvalho, João Paulo, Wilbik, Anna, Bouchon-Meunier, Bernadette, Yager, Ronald, Learning, Fuzzy and Intelligent systems (LFI), LIP6, and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
ComputingMilieux_MISCELLANEOUS, [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

International audience

Published
2020
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23. Cover Feature: Hydrogen Isotope Exchange Catalyzed by Ru Nanocatalysts: Labelling of Complex Molecules Containing N ‐Heterocycles and Reaction Mechanism Insights (Chem. Eur. J. 22/2020)

Author

Sébastien Garcia-Argote, Iker del Rosal, Philippe Lesot, Donia Bouzouita, Laurent Maron, Simon Tricard, Sophie Feuillastre, Marie Certiat, Romuald Poteau, Elodie Marcon, Bruno Chaudret, David-Alexandre Buisson, Viktor Pfeifer, Alberto Palazzolo, Grégory Pieters, Service de Chimie Bio-Organique et de Marquage (SCBM), Médicaments et Technologies pour la Santé (MTS), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Laboratoire de physique et chimie des nano-objets (LPCNO), Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes (IRSAMC), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS), Modélisation Physique et Chimique (LPCNO), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes (IRSAMC), Department of Chemistry and Chemical Biology [Harvard], Harvard University [Cambridge], Laboratoire de Physique Quantique (LPQ), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes (IRSAMC), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Paris-Sud - Paris 11 (UP11)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Harvard University, and Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Reaction mechanism, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Hydrogen isotope, Organic Chemistry, 02 engineering and technology, General Chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Combinatorial chemistry, Catalysis, Nanomaterial-based catalyst, 0104 chemical sciences, Deuterium, Labelling, Molecule, Tritium, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2020
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24. Chemical Synthesis of [ 2 H]-Ethyl Tosylate and Exploration of Its Crypto-optically Active Character Combining Complementary Spectroscopic Tools

Author

Timothée Naret, David-Alexandre Buisson, Philippe Lesot, Sophie Feuillastre, Prasad L. Polavarapu, Andrew R. Puente, Grégory Pieters, Jeanne Crassous, Service de Chimie Bio-Organique et de Marquage (SCBM), Médicaments et Technologies pour la Santé (MTS), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Vanderbilt University [Nashville], Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université Paris-Saclay, Centre National de la Recherche Scientifique, ANR-17-CE11-0014,Carb2zyme,Carb2zyme: Nouvelle chimie pour la formation de liaisons carbone-carbone par une classe émergente de métallo-enzymes(2017), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Deuterium NMR, 010402 general chemistry, 01 natural sciences, Biochemistry, Chemical synthesis, Crypto-chirality, Computational chemistry, QC calculations, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Absolute configuration, Physical and Theoretical Chemistry, Quantum chemical, Quantitative Biology::Biomolecules, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Optically active, Enantiopurity, 0104 chemical sciences, 2H-NMR, Deuterium, Chiral oriented media, VCD analysis, Vibrational circular dichroism, Enantiomer
Abstract

International audience; Small chiral molecules are excellent candidates to push the boundaries of enantiodiscrimination analytical techniques. Here is reported the synthesis of two new deuterated chiral probes, (R)- and (S)-[2H]-ethyl tosylate, obtained with high enantiomeric excesses. Due to their crypto-optically active properties, the discrimination of each enantiomer is challenging. Whereas their enantiopurity is determined by 2H NMR in chiral anisotropic media, their identification was performed by combining quantum chemical calculations and vibrational circular dichroism analysis.

Published
2020
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25. Deuterium Residual Quadrupolar Couplings: Crossing the Current Frontiers in the Relative Configuration Analysis of Natural Products

Author

Philippe Lesot, Roberto R. Gil, P. Berdagué, Armando Navarro-Vázquez, Université Paris-Saclay, Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Carnegie Mellon University [Pittsburgh] (CMU), Federal University of Pernambuco [Recife], and Recurrent funding (CNRS, Université Paris-Saclay)

Subjects
PBLG, Magnetic Resonance Spectroscopy, Materials science, Molecular model, Molecular Conformation, Pharmaceutical Science, Residual, 01 natural sciences, Spectral line, Analytical Chemistry, Relative configuration, 3D molecular structure, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Drug Discovery, Anisotropy, Anisotropic solvent, Pharmacology, chemistry.chemical_classification, Biological Products, Molecular Structure, 010405 organic chemistry, Alignment tensor, Organic Chemistry, Strychnine, Polymer, Deuterium, Artemisinins, Liquid Crystals, 0104 chemical sciences, 3. Good health, 010404 medicinal & biomolecular chemistry, Dipole, Complementary and alternative medicine, chemistry, Lyotropic liquid crystal, Chemical physics, Natural abundance, Natural bioactive products, Molecular Medicine, 2D-NMR
Abstract

International audience; The determination of the 3D structure (configuration and preferred conformation) of complex natural and synthetic organic molecules is a long-standing but still challenging task for chemists, with various implications in pharmaceutical sciences whether or not these substances have specific bioactivities. Nuclear magnetic resonance (NMR) in aligning media, either lyotropic liquid crystals (LLCs) or polymer gels, in combination with molecular modeling is a unique framework for solving complex structural problems whose analytical wealth lies in the establishment of nonlocal structural correlations. As an alternative to the already well-established anisotropic NMR parameters, such as RDCs (residual dipolar couplings) and RCSAs (residual chemical shift anisotropies), it is shown here that deuterium residual quadrupolar couplings (2H-RQCs) can be extracted from 2H 2D-NMR spectra recorded at the natural abundance level in samples oriented in a homopolypeptide LLCs (poly-γ-benzyl-L-glutamate (PBLG)). These 2H-RQCs were successfully used to address nontrivial structural problems in organic molecules. The performance and scope of this new tool is examined for two natural chiral compounds of pharmaceutical interest (strychnine and artemisinin). This is the first report in which the 3D structure/relative configuration of complex bioactive molecules is unambiguously determined using only 2H-RQCs, which, in this case, are at 2H natural abundance.

Published
2020
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26. Determination of the natural deuterium distribution of fatty acids by application of 2H 2D-NMR in liquid crystals: fundamentals, advances, around and beyond

Author

Philippe Lesot, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Recurrent funding (CNRS and Univ. Paris-Sud/Paris-Saclay)

Subjects
PBLG, Materials science, Isotopic distribution, 02 engineering and technology, 01 natural sciences, Isotope fractionation, natural abundance, Computational chemistry, Liquid crystal, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Bioproducts, Prochiral, chiral liquid crystal, General Materials Science, 2D NMR, triglyceride, Fatty acids, chemistry.chemical_classification, 010405 organic chemistry, Fatty acid, General Chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, Deuterium, NAD, 0104 chemical sciences, chemistry, isotope fractionation, fatty acid, 0210 nano-technology, 2D-NMR, Two-dimensional nuclear magnetic resonance spectroscopy, SNIF-NMR
Abstract

International audience; Based on pionneering work reported in the 1980’s by Martin and co-workers, experimental investigation of the site-specific, natural (2H/1H) isotope fractionation in bioproducts by natural abundance deuterium 1D-NMR (NAD 1D-NMR) spectroscopy is the method of choice to understand the enzymatic mechanisms leading to their synthesis or transformation, but also to determine their geographical or botanical origins. This approach, known as 2H-SNIF-NMRTM method, is also an effective tool in the fight against the counterfeiting of molecules of economical interests. However, the use of achiral isotropic solvents has two significant disadvantages that reduce accessible isotopic information: a rate of overlap of signals generally too high for complex analytes and the absence of spectral discrimination of enantiotopic directions in prochiral compounds. Both drawbacks can be overcome by replacing liquid solvents with chiral liquid cristals (CLC). In this review, we overview the theoretical basis and the analytical advantages of anisotropic NAD (ANAD) 2D-NMR using polypeptide-based, lyotropic CLCs as enantiodiscriminating ordered NMR solvents. We discuss how and why ANAD 2D-NMR can provide a robust alternative to the conventional method of determining isotopic ratios, (2H/1H)i, particularly when applied to long-chain fatty acids or homogeneous triglycerides. Various applicative aspects are presented.

Published
2020
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27. Hydrogen isotope exchange catalyzed by Ru nanocatalysts: labelling of complex molecules containing N-heterocycles and reaction mechanism insights

Author

Pfeifer, Viktor, Certiat, Marie, Bouzouita, Donia, Palazzolo, Alberto, Garcia‐Argote, Sébastien, Marcon, Elodie, Buisson, David‐Alexandre, Lesot, Philippe, Maron, Laurent, Chaudret, Bruno, Tricard, Simon, del Rosal, Iker, Poteau, Romuald, Feuillastre, Sophie, Pieters, Grégory, Service de Chimie Bio-Organique et de Marquage (SCBM), Médicaments et Technologies pour la Santé (MTS), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Optoélectronique Quantique (LPCNO), Laboratoire de physique et chimie des nano-objets (LPCNO), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Fédération de recherche « Matière et interactions » (FeRMI), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), HPCs CALcul en MIdiPyrénées (CALMIP-OLYMPE, grant P1415), The Grand Equipement National de Calcul Intensif (GENCI-TGCC, grant 6211), European Project: 675071,H2020,H2020-MSCA-ITN-2015,ISOTOPICS(2016), Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université Paris-Saclay, Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie de Toulouse (ICT-FR 2599), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes (IRSAMC), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Paris-Saclay, Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Université Paris-Saclay, Modélisation Physique et Chimique (LPCNO), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes (IRSAMC), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), We acknowledge HPCs CALcul en MIdiPyrénées (CALMIP-OLYMPE, grant P1415) and the Grand Equipement National de Calcul Intensif (GENCI-TGCC, grant 6211) for generous allocations of computer time., Université de Toulouse (UT)-Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes (IRSAMC), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), and Université Paris-Sud - Paris 11 (UP11)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Heterogeneous catalysis, Full Paper, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Imidazoles, [CHIM.CATA]Chemical Sciences/Catalysis, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Full Papers, nanocatalysis, Deuterium, Tritium, Catalysis, Ruthenium, Heterocyclic Compounds, Deuteration, [CHIM]Chemical Sciences, N-heterocyclic carbenes, C−H Activation, hydrogen isotopic exchange, Isotopic exchange, C-H activation, [CHIM.RADIO]Chemical Sciences/Radiochemistry, Hydrogen
Abstract

Ruthenium nanocatalysis can provide effective deuteration and tritiation of oxazole, imidazole, triazole and carbazole substructures in complex molecules using D2 or T2 gas as isotopic sources. Depending on the substructure considered, this approach does not only represent a significant step forward in practice, with notably higher isotope uptakes, a broader substrate scope and a higher solvent applicability compared to existing procedures, but also the unique way to label important heterocycles using hydrogen isotope exchange. In terms of applications, the high incorporation of deuterium atoms, allows the synthesis of internal standards for LC‐MS quantification. Moreover, the efficacy of the catalyst permits, even under subatmospheric pressure of T2 gas, the preparation of complex radiolabeled drugs owning high molar activities. From a fundamental point of view, a detailed DFT‐based mechanistic study identifying undisclosed key intermediates, allowed a deeper understanding of C−H (and N−H) activation processes occurring at the surface of metallic nanoclusters., Ruthenium nanocatalysis can provide effective deuteration and tritiation of oxazole, imidazole, triazole and carbazole substructures in complex molecules using D2 or T2 gas as isotopic sources. In terms of application, the high incorporation of deuterium atoms allows the synthesis of deuterated internal standards for LC/MS quantification and the efficacy of the catalytic process permits the preparation of complex radiolabelled drugs owning high specific activities by using a subatmospheric pressure of T2 gas.

Published
2020
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28. Multinuclear NMR in Polypeptide Liquid Crystals: Three Fertile Decades of Methodological Developments and Analytical Challenges

Author

Abdelkrim Meddour, Christie Aroulanda, P. Berdagué, Denis Merlet, Jonathan Farjon, Philippe Lesot, Olivier Lafon, Nicolas Giraud, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université Paris Descartes - Paris 5 (UPD5), Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS), Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille, Recurrent funding (CNRS and University Paris-Sud), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes - Faculté des Sciences et des Techniques, Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS), Unité de Catalyse et de Chimie du Solide - UMR 8181 (UCCS), Université d'Artois (UA)-Ecole Centrale de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Université Paris-Sud - Paris 11 (UP11)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)

Subjects
Nuclear and High Energy Physics, Materials science, Oriented media, 010402 general chemistry, 01 natural sciences, Biochemistry, 030218 nuclear medicine & medical imaging, Analytical Chemistry, 03 medical and health sciences, 0302 clinical medicine, Liquid crystal, Computational chemistry, Stereochemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Analytical applications, Anisotropy, Nuclear Magnetic Resonance, Biomolecular, Spectroscopy, Quantitative Biology::Biomolecules, Anisotropic, Stereoisomerism, Nuclear magnetic resonance spectroscopy, Deuterium, NMR, Liquid Crystals, 0104 chemical sciences, NMR spectra database, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Intramolecular force, CLC, Enantiodetection, Enantiomer, Polypeptide, Peptides, Chirality (chemistry), Magnetic dipole–dipole interaction
Abstract

Review on invitation by Prof. Bodenhausen; International audience; NMR spectroscopy of oriented samples makes accessible residual anisotropic intramolecular NMR interactions, such as chemical shift anisotropy (RCSA), dipolar coupling (RDC), and quadrupolar coupling (RQC), while preserving high spectral resolution. In addition, in a chiral aligned environment, enantiomers of chiral molecules or enantiopic elements of prochiral compounds adopt different average orientations on the NMR timescale, and hence produce distinct NMR spectra or signals. NMR spectroscopy in chiral aligned media is a powerful analytical tool, and notably provides unique information on (pro)chirality analysis, natural isotopic fractionation, stereochemistry, as well as molecular conformation and configuration. Significant progress has been made in this area over the three last decades, particularly using polypeptide-based chiral liquid crystals (CLCs) made of organic solutions of helically chiral polymers (as PBLG) in organic solvents. This review presents an overview of NMR in polymeric LCs. In particular, we describe the theoretical tools and the major NMR methods that have been developed and applied to study (pro)chiral molecules dissolved in such oriented solvents. We also discuss the representative applications illustrating the analytical potential of this original NMR tool. This overview article is dedicated to thirty years of original contributions to the development of NMR spectroscopy in polypeptide-based chiral liquid crystals.

Published
2019
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29. Designing and building a low-cost portable FT-NMR spectrometer in 2019: A modern challenge

Author

Philippe Lesot, Alain Louis-Joseph, Laboratoire de synthèse organique (DCSO), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS), and Recurrent funding

Subjects
[PHYS]Physics [physics], Spectrometer, Benchtop, 010405 organic chemistry, General Chemical Engineering, General Chemistry, 010402 general chemistry, 01 natural sciences, NMR, 0104 chemical sciences, visual_art, Magnet, In situ analysis, Electronic component, visual_art.visual_art_medium, Electronic engineering, Electronic design, Low-cost, Field-programmable gate array, Spectroscopy, Realization (systems)
Abstract

High-field Fourier-Transform Nuclear Magnetic Resonance (FT-NMR) spectroscopy is a high performance spectroscopic technique that is essential in many analytical fields. The non-destructive nature of NMR makes it a preferred means of analyzing chemical and biological environments. Compact benchtop NMR spectrometers are low-cost alternatives to conventional high-field and high-resolution spectrometers. A research laboratory may want to develop its own compact FT-NMR spectrometer ("home-built benchtop NMR") with a very low financial cost (∼10 k€). But why? First of all, to use it punctually as an additional channel (nucleus X) to a high-resolution spectrometer, and also to be able to couple it with complementary physics instruments such as an optical microscope to study spin diffusion in semiconductors, for instance. In addition, a "home-built" NMR spectrometer can be used with a low-field permanent magnet for the quantification of species that does not necessarily require high-resolution, avoiding the need for weekly and expensive cryogenic services. Outside the research laboratory, this portable NMR can be used for the in situ analysis of outdoor natural environments. Finally, this compact spectrometer is naturally dedicated to the teaching of NMR technique and is open to the study of the basic electronic functions that constitute an NMR spectrometer. The main question then arises: how to build a robust "Home-Built” NMR? In this article, we describe the realization of an NMR instrument based on electronic components and boards (LNA, ADC, FPGA, ARM, DDS…) easily commercially available, allowing one to obtain a benchtop NMR instrument presenting both a high acquisition dynamics and a good signal-to-noise ratio.

Published
2019
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30. Semi-Supervised Learning and Graph Neural Networks for Fake News Detection

Author

Benjamin Devillers, Manal Saadi, Fragkiskos D. Malliaros, Adrien Benamira, Ayush K. Ray, Etienne Lesot, CentraleSupélec, Centre de vision numérique (CVN), Institut National de Recherche en Informatique et en Automatique (Inria)-CentraleSupélec, OPtimisation Imagerie et Santé (OPIS), Inria Saclay - Ile de France, Institut National de Recherche en Informatique et en Automatique (Inria)-Institut National de Recherche en Informatique et en Automatique (Inria)-Centre de vision numérique (CVN), and Institut National de Recherche en Informatique et en Automatique (Inria)-CentraleSupélec-CentraleSupélec

Subjects
Fake news detection, Artificial neural network, business.industry, Computer science, Binary number, 02 engineering and technology, Semi-supervised learning, Machine learning, computer.software_genre, Electronic mail, [INFO.INFO-SI]Computer Science [cs]/Social and Information Networks [cs.SI], Graph neural networks, [INFO.INFO-LG]Computer Science [cs]/Machine Learning [cs.LG], 020204 information systems, 0202 electrical engineering, electronic engineering, information engineering, Task analysis, Disinformation, Graph (abstract data type), 020201 artificial intelligence & image processing, Social media, [INFO]Computer Science [cs], Artificial intelligence, business, computer
Abstract

International audience; Social networks have become the main platforms for information dissemination. Nevertheless, due to the increasing number of users, social media platforms tend to be highly vulnerable to the propagation of disinformation-making the detection of fake news a challenging task. In this work, we focus on content-based methods for detecting fake news-casting the problem to a binary text classification one (an article corresponds to either fake news or not). The main challenge here stems from the fact that the number of labeled data is limited; very few articles can be examined and annotated as fake. To this extend, we opted for semi-supervised learning approaches. In particular, our work proposes a graph-based semi-supervised fake news detection method, based on graph neural networks. The experimental results indicate that the proposed methodology achieves better performance compared to traditional classification techniques, especially when trained on limited number of labeled articles.

Published
2019

31. The Dangers of Post-hoc Interpretability: Unjustified Counterfactual Explanations

Author

Xavier Renard, Marie-Jeanne Lesot, Marcin Detyniecki, Thibault Laugel, Christophe Marsala, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), AXA France, AXA, and Polish Academy of Sciences (PAN)

Subjects
FOS: Computer and information sciences, Counterfactual thinking, Computer Science - Machine Learning, 0303 health sciences, Post hoc, Computer Science - Artificial Intelligence, Computer science, Machine Learning (stat.ML), 02 engineering and technology, Machine Learning (cs.LG), [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI], 03 medical and health sciences, Artificial Intelligence (cs.AI), [INFO.INFO-LG]Computer Science [cs]/Machine Learning [cs.LG], Statistics - Machine Learning, 0202 electrical engineering, electronic engineering, information engineering, Econometrics, 020201 artificial intelligence & image processing, 030304 developmental biology, Interpretability
Abstract

International audience; Post-hoc interpretability approaches have been proven to be powerful tools to generate explanations for the predictions made by a trained black-box model. However, they create the risk of having explanations that are a result of some artifacts learned by the model instead of actual knowledge from the data. This paper focuses on the case of counterfactual explanations and asks whether the generated instances can be justified, i.e. continuously connected to some ground-truth data. We evaluate the risk of generating unjustified counter-factual examples by investigating the local neighborhoods of instances whose predictions are to be explained and show that this risk is quite high for several datasets. Furthermore, we show that most state of the art approaches do not differentiate justified from unjustified counterfactual examples, leading to less useful explanations.

Published
2019
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32. A proximal framework for fuzzy subspace clustering

Author

Christophe Marsala, Marie-Jeanne Lesot, Arthur Guillon, Learning, Fuzzy and Intelligent systems (LFI), LIP6, and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
0209 industrial biotechnology, Optimization problem, Logic, 02 engineering and technology, Function (mathematics), Linear subspace, Expression (mathematics), Term (time), [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI], Euclidean distance, 020901 industrial engineering & automation, Operator (computer programming), [INFO.INFO-LG]Computer Science [cs]/Machine Learning [cs.LG], Artificial Intelligence, 0202 electrical engineering, electronic engineering, information engineering, 020201 artificial intelligence & image processing, Cluster analysis, Algorithm, ComputingMilieux_MISCELLANEOUS, Mathematics
Abstract

This paper proposes a fuzzy partitioning subspace clustering algorithm that minimizes a variant of the FCM cost function with a weighted Euclidean distance and a non-differentiable penalty term. The form of the cost function suggests to split the optimization problem, taking advantage of the framework of proximal optimization. The expression of the proximal operator for the penalty term is derived and implemented in a new algorithm, PFSCM, which combines proximal descent and alternate optimization. A discussion on the extension of this work to produce sparse estimations of the subspaces is conducted. Experimental results show the relevance of the proposed approach.

Published
2019
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33. FRELS: Fast and Reliable Estimated Linguistic Summaries

Author

Olivier Pivert, Grégory Smits, Pierre Nerzic, Marie-Jeanne Lesot, Symbolic and Human-centric view of dAta MANagement (SHAMAN), GESTION DES DONNÉES ET DE LA CONNAISSANCE (IRISA-D7), Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), SMITS, Grégory, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)

Subjects
Vocabulary, [INFO.INFO-DB]Computer Science [cs]/Databases [cs.DB], Computer science, Relational database, media_common.quotation_subject, Reliability (computer networking), Process (computing), 02 engineering and technology, Automatic summarization, Fuzzy logic, Linguistics, 020204 information systems, Histogram, [INFO.INFO-IR]Computer Science [cs]/Information Retrieval [cs.IR], 0202 electrical engineering, electronic engineering, information engineering, [INFO.INFO-DB] Computer Science [cs]/Databases [cs.DB], 020201 artificial intelligence & image processing, [INFO.INFO-IR] Computer Science [cs]/Information Retrieval [cs.IR], Tuple, media_common
Abstract

International audience; The linguistic summarization of a dataset is a process whose complexity depends linearly on the size of the dataset and exponentially on the size of the fuzzy vocabulary. To efficiently summarize large datasets stored in Relational DataBases, reliable estimated cardinalities can be derived from statistics about the data distribution maintained by the RDB Management System, with no expensive data scans. This paper proposes to improve the precision of such estimated summaries while preserving their efficiency, by enriching the statistics-based approach with local scan-based corrections when needed: the proposed FRELS method provides efficient strategies both for identifying the needs and performing the corrections. Experiments conducted on real data show that FRELS remains incomparably more efficient than data-scan-based approaches to data summarization and offers a better precision than purely statistics-based approaches. The generation of estimated linguistic summaries takes a couple of seconds, even for datasets containing millions of tuples, with a reliability of more than 95%.

Published
2019

34. Study of an Abating Aggregation Operator in Many-Valued Logic

Author

Revault d'Allonnes, Adrien, Lesot, Marie-Jeanne, Laboratoire d'Informatique Avancée de Saint-Denis (LIASD), Université Paris 8 Vincennes-Saint-Denis (UP8), Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), and Revault d'Allonnes, Adrien

Subjects
[INFO.INFO-AI] Computer Science [cs]/Artificial Intelligence [cs.AI], [INFO]Computer Science [cs], [INFO] Computer Science [cs], [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

International audience; This paper considers a parametrised aggregation operator, originally introduced in the formal framework of many-valued logic and in the applicative context of information scoring. It studies this operator, outside this applicative context, looking at specific configurations of interest: highlighting the wide range of its instantiations, from the lower to the upper extreme cases; showing some t-norms it can encode, as specific cases; and also how it allows rich and flexible intermediate behaviours.

Published
2019

35. If I don’t know, should I infer? Reasoning around ignorance in a many-valued framework

Author

Revault d'Allonnes, Adrien, Lesot, Marie-Jeanne, Laboratoire d'Informatique Avancée de Saint-Denis (LIASD), Université Paris 8 Vincennes-Saint-Denis (UP8), Learning, Fuzzy and Intelligent systems (LFI), Laboratoire d'Informatique de Paris 6 (LIP6), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Lesot, Marie-Jeanne

Subjects
[INFO.INFO-AI] Computer Science [cs]/Artificial Intelligence [cs.AI], [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

International audience; —Many-valued logic allows to reason with partial truth measured by degrees on a discrete scale, but it suffers from an ambiguous interpretation of the middle truth level, considered as intermediate truth or as ignorance, i.e. inability to assess truth. The L e M extension introduces an additional value, outside the truth scale, to distinguish between these two notions. This paper studies L e M from a logical perspective, examining how to reason in this framework: it discusses the definition of appropriate semantics for the logical connectives and it considers an inference task, proposing a Modus Ponens variant for L e M .

Published
2017

36. (Cover Profile) 2H and 13C NMR-Based Enantiodetection Using Polyacetylene versus Polypeptide Aligning Media: Versatile and Complementary Tools for Chemists

Author

Philippe Lesot, Philippe Berdagué, Abdelkrim Meddour, Alexander Kreiter, Markus Noll, Michael Reggelin, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS), and Technische Universität Darmstadt (TU Darmstadt)

Subjects
010405 organic chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Cover profile, General Chemistry, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences
Abstract

International audience; Invited for this month’s cover are the collaborating groups of Dr. Philippe Lesot (DR CNRS) at Universit Paris-Sud/UniversitParis-Saclay, France, and Professor Michael Reggelin at TU Darmstadt, Germany. The cover shows the proton-decoupled natural abundance deuterium (NAD-{1H}) Q-resolved Fz 2D-NMR spectrum of ()-3-methylhexane measured in the anisotropic lyotropic chiral liquid-crystalline phase formed by a concentrated solution of a helically chiral polyarylacetylene in chloroform solvent. Seventeen out of the twenty possible deuterium quadrupolar doublets are observed, demonstrating the enormous enantiodifferentiating capability of the system, even for an unfunctionalized chiral alkane. Read the full text of the article at 10.1002/cplu.201800493.

Published
2019
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37. 2H and 13C NMR-Based Enantiodetection Using Polyacetylene versus Polypeptide Aligning Media: Versatile and Complementary Tools for Chemists

Author

Alexander Kreiter, Markus Noll, Michael Reggelin, P. Berdagué, Abdelkrim Meddour, Philippe Lesot, Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Technische Universität Darmstadt (TU Darmstadt), and Recurrent funding from CNRS and University of Paris-Sud

Subjects
PBLG, Materials science, 010402 general chemistry, 01 natural sciences, Molecular dynamics, Polyacetylene, chemistry.chemical_compound, Computational chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Chirality, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Enantiodiscrimination, Enantiomorphism, General Chemistry, Nuclear magnetic resonance spectroscopy, Carbon-13 NMR, NMR, 0104 chemical sciences, Mesophase, Chiral model, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Lyotropic liquid crystal, Racemic mixture, PLA, Enantiomer
Abstract

International audience; In this work, the practical/analytical potential of an L-valinederived polyacetylene (PLA) lyotropic liquid crystal (LLC) isexamined to spectrally discriminate enantiomers (racemic mixture) or enantiotopic directions of a large collection (23) of(pro)chiral model compounds (from rigid to flexible and polar to apolar ones), thus covering various important aspects ofenantiomorphism. Experimental 2H-{1H} (deuterated analytes and at natural abundance level) and 13C-{1H} NMR results are discussed in terms of the difference of 2H-RQCs or 13C-RCSAs and compared to those obtained in polypeptide-type LLCs (PBLG). The analysis of the NMR results provides an overview of the enantiodifferentiation capabilities of PLA and gives useful/ practical hints for the chemist to select the most appropriate chiral oriented system. Astonishing NAD NMR results wereobtained in the case of one of the simplest, chiral alkanes, 3-methylhexane. From a theoretical viewpoint, the data collected highlight the key molecular factors involved in orientation/discrimination processes, as a basis for optimizing computationalprediction (molecular dynamics simulation), as well asdesigning novel helically chiral polymers as new enantiodiscriminating aligning media. In addition, a new, robust and efficientprotocol to synthesize PLA and its enantiomer (PDA) on a large scale and with small polydispersities is proposed.

Published
2019
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38. ROHSA: Regularized Optimization for Hyper-Spectral Analysis: Application to phase separation of 21 cm data

Author

marchal, antoine, Miville-Deschênes, Marc-Antoine, Orieux, François, Gac, Nicolas, Soussen, Charles, Lesot, Marie-Jeanne, Revault d'Allonnes, Adrien, Salomé, Quentin, Astrophysique Interprétation Modélisation (AIM (UMR_7158 / UMR_E_9005 / UM_112)), Centre National de la Recherche Scientifique (CNRS)-Institut national des sciences de l'Univers (INSU - CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris Diderot - Paris 7 (UPD7), Laboratoire des signaux et systèmes (L2S), Centre National de la Recherche Scientifique (CNRS)-CentraleSupélec-Université Paris-Sud - Paris 11 (UP11), Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Laboratoire d'Informatique Avancée de Saint-Denis (LIASD), Université Paris 8 Vincennes-Saint-Denis (UP8), Laboratoire d'études spatiales et d'instrumentation en astrophysique (LESIA (UMR_8109)), Institut national des sciences de l'Univers (INSU - CNRS)-Observatoire de Paris, PSL Research University (PSL)-PSL Research University (PSL)-Université Paris Diderot - Paris 7 (UPD7)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Université Paris-Sud - Paris 11 (UP11)-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université Paris Diderot - Paris 7 (UPD7)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Astrophysique Interprétation Modélisation (AIM (UMR7158 / UMR_E_9005 / UM_112)), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut national des sciences de l'Univers (INSU - CNRS)-Université Paris Diderot - Paris 7 (UPD7)-Centre National de la Recherche Scientifique (CNRS)

Subjects
ISM: kinematics and dynamics, ISM: structure, methods: observational, [PHYS.ASTR]Physics [physics]/Astrophysics [astro-ph], methods: data analysis, ISM: clouds, [SPI.SIGNAL]Engineering Sciences [physics]/Signal and Image processing, methods: numerical
Abstract

20 pages, 21 figures; Accepted for publication in A&A; International audience; Context. Extracting the multiphase structure of the neutral interstellar medium is key to understanding star formation in galaxies. The radiative condensation of the diffuse warm neutral medium producing a thermally unstable lukewarm medium and a dense cold medium is closely related to the initial step leading the atomic-to-molecular (HI-to-H2) transition and the formation of molecular clouds. Up to now, the mapping of these phases out of 21 cm emission hyper-spectral cubes has remained elusive mostly due to the velocity blending of individual cold structures present on a given line of sight. As a result, most of the current knowledge about the HI phases rests on a small number of absorption measurements on lines of sight crossing radio sources.Aims. The goal of this work is to develop a new algorithm to perform separation of diffuse sources in hyper-spectral data. Specifically the algorithm was designed in order to address the velocity blending problem by taking advantage of the spatial coherence of the individual sources. The main scientific driver of this effort was to extract the multiphase structure of the HI from 21 cm line emission only, providing a means to map each phase separately, but the algorithm developed here should be generic enough to extract diffuse structures in any hyper-spectral cube.Methods. We developed a new Gaussian decomposition algorithm named ROHSA based on a multi-resolution process from coarse to fine grid. ROHSA uses a regularized nonlinear least-square criterion to take into account the spatial coherence of the emission and the multiphase nature of the gas simultaneously. In order to obtain a solution with spatially smooth parameters, the optimization is performed on the whole data cube at once. The performances of ROHSA were tested on a synthetic observation computed from numerical simulations of thermally bi-stable turbulence. We apply ROHSA to a 21 cm observation of a region of high Galactic latitude from the GHIGLS survey and present our findings.Results. The evaluation of ROHSA on synthetic 21 cm observations shows that it is able to recover the multiphase nature of the HI. For each phase, the power spectra of the column density and centroid velocity are well recovered. More generally, this test reveals that a Gaussian decomposition of HI emission is able to recover physically meaningful information about the underlying three-dimensional fields (density, velocity, and temperature). The application on a real 21 cm observation of a field of high Galactic latitude produces a picture of the multiphase HI, with isolated, filamentary, and narrow (σ ~ 1−2 km s−1) structures, and broader (σ ~ 4−10 km s−1), diffuse, and space-filling components. The test-case field used here contains significant intermediate-velocity clouds that were well mapped out by the algorithm. As ROHSA is designed to extract spatially coherent components, it performs well at projecting out the noise.Conclusions. In this paper we introduce ROHSA, a new algorithm that performs a separation of diffuse sources in hyper-spectral data on the basis of a Gaussian decomposition. The algorithm makes no assumption about the nature of the sources, except that each one has a similar line width. The tests we made shows that ROHSA is well suited to decomposing complex 21 cm line emission of regions of high Galactic latitude, but its design is general enough that it could be applied to any hyper-spectral data type for which a Gaussian model is relevant.

Published
2019
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39. Régularisation laplacienne pour le subspace clustering

Author

Guillon, Arthur, Lesot, Marie-Jeanne, Marsala, Christophe, Learning, Fuzzy and Intelligent systems (LFI), LIP6, and Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[INFO.INFO-LG]Computer Science [cs]/Machine Learning [cs.LG], [INFO]Computer Science [cs], ComputingMilieux_MISCELLANEOUS, [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

International audience

Published
2018

40. Génération efficace de résumés linguistiques estimés

Author

Smits, Grégory, Nerzic, Pierre, Pivert, Olivier, Lesot, Marie-Jeanne, Symbolic and Human-centric view of dAta MANagement (SHAMAN), GESTION DES DONNÉES ET DE LA CONNAISSANCE (IRISA-D7), Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)

Subjects
[INFO.INFO-DB]Computer Science [cs]/Databases [cs.DB], ComputingMilieux_MISCELLANEOUS
Abstract

National audience

Published
2018

41. OSACA: Discovering Ordinal Categorical Attributes

Author

Marsala, Christophe, Laurent, Anne, Lesot, Marie-Jeanne, Rifqi, Maria, Castelltort, Arnaud, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), WEB-CUBE, Laboratoire d'Informatique de Robotique et de Microélectronique de Montpellier (LIRMM), Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM), Laboratoire d'économie mathématique et de microéconomie appliquée (LEMMA), and Université Panthéon-Assas (UP2)-Sorbonne Université (SU)

Subjects
Gradual Patterns, Mesure d'entropie d'ordre, Rank Discrimination Measure, [INFO.INFO-LG]Computer Science [cs]/Machine Learning [cs.LG], Motifs graduels, Ordinal Attributes, [INFO]Computer Science [cs], Mathematical Morphology, Attributs ordinaux, Morphologie mathématique, [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

International audience; This paper proposes to exploit heterogeneous data, i.e. data described by both numerical and categorical features, so as to discover whether, based on information provided by the numerical attributes, some categorical attributes actually are ordinal ones. The proposed 3-step methodology OSACA, first extracts gradual patterns from the numerical attributes ; it then applies mathematical morphology tools to induce an associated order on the categorical attributes. The third step evaluates the quality of the candidate rankings through measures derived from the rank entropy discrimination.; Les bases de données dites hétérogènes contiennent des données décrites par des attributsà la fois symboliques et numériques. Cet article propose une méthode, appelée OSACA, pour identifier, parmi les attributs symboliques, les attributs ordinaux, en exploitant les informations fournies par les attributs numériques. Pour ce faire, OSACA procède en trois étapes : des motifs graduels sont d'abord extraits des attributs numériques. Des filtres morphologiques sont ensuite appliqués aux attributs symboliques pour déterminer des ordres sur les valeurs catégoriellesà partir de l'ordre induit par les motifs graduels. Enfin, une mesure d'entropie d'ordre per-met d'évaluer la pertinence des ordres candidats.

Published
2018

42. OSACA: Découverte d'attributs symboliques ordinaux

Author

Marsala, Christophe, Laurent, Anne, Lesot, Marie-Jeanne, Rifqi, Maria, Castelltort, Arnaud, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), WEB-CUBE, Laboratoire d'Informatique de Robotique et de Microélectronique de Montpellier (LIRMM), Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM), Laboratoire d'économie mathématique et de microéconomie appliquée (LEMMA), and Université Panthéon-Assas (UP2)-Sorbonne Université (SU)

Subjects
Gradual Patterns, Mesure d'entropie d'ordre, Rank Discrimination Measure, [INFO.INFO-LG]Computer Science [cs]/Machine Learning [cs.LG], Motifs graduels, Ordinal Attributes, [INFO]Computer Science [cs], Mathematical Morphology, Attributs ordinaux, Morphologie mathématique, [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

International audience; This paper proposes to exploit heterogeneous data, i.e. data described by both numerical and categorical features, so as to discover whether, based on information provided by the numerical attributes, some categorical attributes actually are ordinal ones. The proposed 3-step methodology OSACA, first extracts gradual patterns from the numerical attributes ; it then applies mathematical morphology tools to induce an associated order on the categorical attributes. The third step evaluates the quality of the candidate rankings through measures derived from the rank entropy discrimination.; Les bases de données dites hétérogènes contiennent des données décrites par des attributsà la fois symboliques et numériques. Cet article propose une méthode, appelée OSACA, pour identifier, parmi les attributs symboliques, les attributs ordinaux, en exploitant les informations fournies par les attributs numériques. Pour ce faire, OSACA procède en trois étapes : des motifs graduels sont d'abord extraits des attributs numériques. Des filtres morphologiques sont ensuite appliqués aux attributs symboliques pour déterminer des ordres sur les valeurs catégoriellesà partir de l'ordre induit par les motifs graduels. Enfin, une mesure d'entropie d'ordre per-met d'évaluer la pertinence des ordres candidats.

Published
2018

43. Discovering Ordinal Attributes Through Gradual Patterns, Morphological Filters and Rank Discrimination Measures

Author

Christophe Marsala, Marie-Jeanne Lesot, Maria Rifqi, Anne Laurent, Arnaud Castelltort, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), WEB-CUBE, Laboratoire d'Informatique de Robotique et de Microélectronique de Montpellier (LIRMM), Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM), Laboratoire d'économie mathématique et de microéconomie appliquée (LEMMA), Université Panthéon-Assas (UP2)-Sorbonne Université (SU), Ciucci D., Pasi G., and Vantaggi B.

Subjects
[INFO.INFO-DB]Computer Science [cs]/Databases [cs.DB], Exploit, Computer science, Gradual patterns, 020207 software engineering, 02 engineering and technology, Ordinal attributes, Mathematical morphology, computer.software_genre, [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI], Rank discrimination measure, 0202 electrical engineering, electronic engineering, information engineering, Heterogeneous data, Entropy (information theory), 020201 artificial intelligence & image processing, Data mining, Categorical variable, computer
Abstract

International audience; This paper proposes to exploit heterogeneous data, i.e. data described by both numerical and categorical features, so as to gain knowledge about the categorical attributes from the numerical ones. More precisely, it aims at discovering whether, according to a given data set, based on information provided by the numerical attributes, some categorical attributes actually are ordinal ones and, additionally, at establishing ranking relations between the category values. To that aim, the paper proposes the 3-step methodology OSACA, standing for Order Seeking Algorithm for Categorical Attributes: it first consists in extracting gradual patterns from the numerical attributes, to identify rich ranking information about the data; it then applies mathematical morphology tools, more precisely alternated filters, to induce an associated order on the categorical attributes. The third step evaluates the quality of the candidate rankings through an original measure derived from the rank entropy discrimination.

Published
2018
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44. Defining Locality for Surrogates in Post-hoc Interpretablity

Author

Laugel, Thibault, Renard, Xavier, Lesot, Marie-Jeanne, Marsala, Christophe, Detyniecki, Marcin, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), AXA France, AXA, and Polish Academy of Sciences (PAN)

Subjects
FOS: Computer and information sciences, Computer Science - Learning, Artificial Intelligence (cs.AI), [INFO.INFO-LG]Computer Science [cs]/Machine Learning [cs.LG], Computer Science - Artificial Intelligence, Statistics - Machine Learning, Machine Learning (stat.ML), [STAT.OT]Statistics [stat]/Other Statistics [stat.ML], Machine Learning (cs.LG), [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI]
Abstract

Local surrogate models, to approximate the local decision boundary of a black-box classifier, constitute one approach to generate explanations for the rationale behind an individual prediction made by the back-box. This paper highlights the importance of defining the right locality, the neighborhood on which a local surrogate is trained, in order to approximate accurately the local black-box decision boundary. Unfortunately, as shown in this paper, this issue is not only a parameter or sampling distribution challenge and has a major impact on the relevance and quality of the approximation of the local black-box decision boundary and thus on the meaning and accuracy of the generated explanation. To overcome the identified problems, quantified with an adapted measure and procedure, we propose to generate surrogate-based explanations for individual predictions based on a sampling centered on particular place of the decision boundary, relevant for the prediction to be explained, rather than on the prediction itself as it is classically done. We evaluate the novel approach compared to state-of-the-art methods and a straightforward improvement thereof on four UCI datasets., presented at 2018 ICML Workshop on Human Interpretability in Machine Learning (WHI 2018), Stockholm, Sweden

Published
2018

45. Efficient Generation of Reliable Estimated Linguistic Summaries

Author

Olivier Pivert, Marie-Jeanne Lesot, Pierre Nerzic, Grégory Smits, Symbolic and Human-centric view of dAta MANagement (SHAMAN), GESTION DES DONNÉES ET DE LA CONNAISSANCE (IRISA-D7), Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS), Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche en Informatique et Systèmes Aléatoires (IRISA), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Bretagne Sud (UBS)-École normale supérieure - Rennes (ENS Rennes)-Institut National de Recherche en Informatique et en Automatique (Inria)-Télécom Bretagne-CentraleSupélec-Centre National de la Recherche Scientifique (CNRS)

Subjects
Soft computing, [INFO.INFO-DB]Computer Science [cs]/Databases [cs.DB], Computer science, Relational database, 02 engineering and technology, Automatic summarization, Electronic mail, Linguistics, Visualization, Data access, 020204 information systems, [INFO.INFO-IR]Computer Science [cs]/Information Retrieval [cs.IR], 0202 electrical engineering, electronic engineering, information engineering, 020201 artificial intelligence & image processing, Tuple
Abstract

International audience; Summarizing data with linguistic statements is a crucial and topical issue that has been largely addressed by the soft computing community. The goal of summarization is to generate statements that linguistically describe the properties observed in a dataset. This paper addresses the issue of efficiently extracting these summaries and rendering them to the final user, in the case where the data to be summarized are stored in a relational data base: it proposes a novel strategy that leverages the statistics about the data distribution maintained by the database system. This paper shows that reliable summaries can be very efficiently estimated based on these statistics only and without any costly data access. Additionally, it proposes a visualization of the set of extracted summaries that offers a fruitful interactive exploration tool to the user. Experiments performed on two real data bases show the relevance and efficiency of the proposed approach: with a negligible loss of accuracy, we provide the first linguistic summarization approach whose processing time does not depend on the size of the dataset. The generation of estimated linguistic summaries takes less than one second even for dataset containing millions of tuples.

Published
2018

46. Comparison-based Inverse Classification for Interpretability in Machine Learning

Author

Christophe Marsala, Thibault Laugel, Marcin Detyniecki, Xavier Renard, Marie-Jeanne Lesot, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Groupe AXA (AXA), Jesús Medina, Manuel Ojeda-Aciego, José Luis Verdegay, David A. Pelta, Inma P. Cabrera, Bernadette Bouchon-Meunier, and Ronald R. Yager

Subjects
Computer science, business.industry, 05 social sciences, Closeness, 050301 education, Inverse, 02 engineering and technology, Machine learning, computer.software_genre, comparison-based, [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI], [INFO.INFO-LG]Computer Science [cs]/Machine Learning [cs.LG], Close neighbor, 0202 electrical engineering, electronic engineering, information engineering, local explanation, 020201 artificial intelligence & image processing, Artificial intelligence, post-hoc interpretability, business, inverse classification, 0503 education, computer, Classifier (UML), Interpretability, Test data
Abstract

International audience; In the context of post-hoc interpretability, this paper addresses the task of explaining the prediction of a classifier, considering the case where no information is available, neither on the classifier itself , nor on the processed data (neither the training nor the test data). It proposes an inverse classification approach whose principle consists in determining the minimal changes needed to alter a prediction: in an instance-based framework, given a data point whose classification must be explained, the proposed method consists in identifying a close neighbor classified differently, where the closeness definition integrates a spar-sity constraint. This principle is implemented using observation generation in the Growing Spheres algorithm. Experimental results on two datasets illustrate the relevance of the proposed approach that can be used to gain knowledge about the classifier.

Published
2018
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47. Dynamic Trust Scoring of Railway Sensor Information

Author

Andrzej Bielecki, Teodora Petrisor, Adrien Revault d'Allonnes, Marie-Jeanne Lesot, Marcin Lenart, Learning, Fuzzy and Intelligent systems (LFI), LIP6, Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Thales Research and Technology [Palaiseau], THALES, AGH University of Science and Technology [Krakow, PL] (AGH UST), Laboratoire d'Informatique Avancée de Saint-Denis (LIASD), Université Paris 8 Vincennes-Saint-Denis (UP8), Learning, Fuzzy and Intelligent systems ( LFI ), Laboratoire d'Informatique de Paris 6 ( LIP6 ), Université Pierre et Marie Curie - Paris 6 ( UPMC ) -Centre National de la Recherche Scientifique ( CNRS ) -Université Pierre et Marie Curie - Paris 6 ( UPMC ) -Centre National de la Recherche Scientifique ( CNRS ), AGH University of Science and Technology [Pologne], AGH University of Science and Technology, Laboratoire d'Informatique Avancée de Saint-Denis ( LIASD ), and Université Paris 8 Vincennes-Saint-Denis ( UP8 )

Subjects
Value (ethics), [ INFO ] Computer Science [cs], Computer science, likelihood, 02 engineering and technology, Machine learning, computer.software_genre, Domain (software engineering), Task (project management), credibility, [INFO.INFO-AI]Computer Science [cs]/Artificial Intelligence [cs.AI], sensor, 020204 information systems, Component (UML), Credibility, 0202 electrical engineering, electronic engineering, information engineering, [INFO]Computer Science [cs], [ INFO.INFO-AI ] Computer Science [cs]/Artificial Intelligence [cs.AI], Reliability (statistics), reliability, business.industry, trust, Fuse (electrical), 020201 artificial intelligence & image processing, Artificial intelligence, information scoring, business, computer
Abstract

International audience; A sensor can encounter many situations where its readings can be untrustworthy and the ability to recognise this is an important and challenging task. It opens the possibility to assess sensors for forensic or maintenance purposes, compare them or fuse their information. We present a proposition to score a piece of information produced by a sensor as an aggregation of three dimensions called reliability, likelihood and credibility into a trust value that take into account a temporal component. The approach is validated on data from the railway domain.

Published
2018
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48. Fuzzy inferences using geometric compatibility or using graduality and ambiguity constraints

Author

Valerie Cross, Marie-Jeanne Lesot, Lesot, Marie-Jeanne, Learning, Fuzzy and Intelligent systems (LFI), Laboratoire d'Informatique de Paris 6 (LIP6), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
0209 industrial biotechnology, business.industry, media_common.quotation_subject, Classical logic, Inference, 02 engineering and technology, Ambiguity, Disjoint sets, [INFO] Computer Science [cs], Fuzzy logic, 020901 industrial engineering & automation, Compatibility (mechanics), 0202 electrical engineering, electronic engineering, information engineering, 020201 artificial intelligence & image processing, [INFO]Computer Science [cs], Artificial intelligence, Transposition (logic), Modus ponens, business, ComputingMilieux_MISCELLANEOUS, media_common, Mathematics
Abstract

In classical logic, Modus Ponens allows to infer new knowledge in the case where the antecedent of a given rule is observed, establishing that the rule conclusion then holds. Approximate reasoning extends the principle to the case where the observation does not totally match the rule antecedent. Several approaches have been proposed to deal with the extreme case where the observation is actually disjoint from the rule antecedent, using different principles to guide inference and avoid producing total uncertainty. This paper studies two of them, namely Geometric Compatibility Modification (GCM) and the Transformation-based Constraint-Guided Generalised Modus Ponens (T-CGMP), that respectively perform a type of approximate analogical reasoning and extend the GMP: it provides an indepth comparison, to determine their relationships, common points and distinct features. It thus provides guidelines for the definition of fuzzy inference schemes.

Published
2017

49. Transformation-based constraint-guided Generalised Modus Ponens

Author

Michael Blot, Marcin Detyniecki, Marie-Jeanne Lesot, Learning, Fuzzy and Intelligent systems (LFI), Laboratoire d'Informatique de Paris 6 (LIP6), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Lesot, Marie-Jeanne, and Machine Learning and Information Access (MLIA)

Subjects
Deduction theorem, business.industry, Inference, 02 engineering and technology, Fuzzy control system, [INFO] Computer Science [cs], Computer Science::Logic in Computer Science, Premise, 0202 electrical engineering, electronic engineering, information engineering, Fuzzy number, Fuzzy set operations, 020201 artificial intelligence & image processing, [INFO]Computer Science [cs], Artificial intelligence, business, Modus ponens, Rule of inference, ComputingMilieux_MISCELLANEOUS, Mathematics
Abstract

Generalised Modus Ponens (GMP) allows to perform logical inference in the case where an observation partially matches the premise of an implication, enriching the rule exploitation as compared to binary classical logic. This paper proposes to further enhance the rule exploitation, integrating additional constraints to guide the inference, both to reduce uncertainty in case of partial match and to perform inference in the case of an observation disjoint from the rule premise. These constraints are expressed as logical predicates derived from properties that characterise the observation, in an absolute way or relatively to the rule premise. An extension of GMP is proposed, to take into account the constraints, based on transformation operations applied to the fuzzy sets involved in the rule and the observation. An instantiation to a GMP preserving graduality and ambiguity is established and its validity is proven.

Published
2016

50. Nuclear Magnetic Resonance Spectroscopy-Applicable Elements—Hydrogen Isotopes: 2 H NMR

Author

Philippe Lesot, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Centre National de la Recherche Scientifique (CNRS)

Subjects
liquids, Materials science, Hydrogen, Isotope, 010405 organic chemistry, Liquid crystals, chemistry.chemical_element, Nuclear magnetic resonance spectroscopy, 010402 general chemistry, Deuterium, 01 natural sciences, NMR, 0104 chemical sciences, chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Proton NMR, Physical chemistry, Solids, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018
Full Text
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