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Three dermacozines, dermacozines N-P ( 1 - 3 ), were isolated from the piezotolerant Actinomycete strain Dermacoccus abyssi MT 1.1 T , which was isolated from a Mariana Trench sediment in 2006. Herein, we report the elucidation of their structures using a combination of 1D/2D NMR, LC-HRESI-MS n , UV-Visible, and IR spectroscopy. Further confirmation of the structures was achieved through the analysis of data from density functional theory (DFT)-UV-Visible spectral calculations and statistical analysis such as two tailed t -test, linear regression-, and multiple linear regression analysis applied to either solely experimental or to experimental and calculated 13 C-NMR chemical shift data. Dermacozine N ( 1 ) bears a novel linear pentacyclic phenoxazine framework that has never been reported as a natural product. Dermacozine O ( 2 ) is a constitutional isomer of the known dermacozine F while dermacozine P ( 3 ) is 8-benzoyl-6-carbamoylphenazine-1-carboxylic acid. Dermacozine N ( 1 ) is unique among phenoxazines due to its near infrared (NIR) absorption maxima, which would make this compound an excellent candidate for research in biosensing chemistry, photodynamic therapy (PDT), opto-electronic applications, and metabolic mapping at the cellular level. Furthermore, dermacozine N ( 1 ) possesses weak cytotoxic activity against melanoma (A2058) and hepatocellular carcinoma cells (HepG2) with IC 50 values of 51 and 38 μM, respectively.