6-[2-(4,4-dimethyl-1-oxo-3,4-dihydro-2H-1λ4-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylic acid

• ChemBase ID: 178098
• Molecular Formular: C19H17NO3S
• Molecular Mass: 339.40818
• Monoisotopic Mass: 339.09291441
• SMILES: C1CS(=O)c2c(C1(C)C)cc(cc2)C#Cc1ncc(cc1)C(=O)O
• Canonical SMILES: OC(=O)c1ccc(nc1)C#Cc1ccc2c(c1)C(C)(C)CCS2=O
• InChI: InChI=1S/C19H17NO3S/c1-19(2)9-10-24(23)17-8-4-13(11-16(17)19)3-6-15-7-5-14(12-20-15)18(21)22/h4-5,7-8,11-12H,9-10H2,1-2H3,(H,21,22)
• InChIKey: SMCJVZRFBIOWHW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[2-(4,4-dimethyl-1-oxo-3,4-dihydro-2H-1λ^4-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylic acid
• IUPAC Traditional name: 6-[2-(4,4-dimethyl-1-oxo-2,3-dihydro-1λ^4-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylic acid
• Synonyms: 6-[2-(3,4-Dihydro-4,4-dimethyl-1-oxido-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic Acid; 6-[(3,4-Dihydro-4,4-dimethyl-1-oxido-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic Acid; Tazarotenic Acid Sulfoxide

Database IDs

• CAS Number: 603952-64-3
• PubChem SID: 164234008
• PubChem CID: 66870917

CALCULATED PROPERTIES

• Acid pKa: 3.762053
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.1311456
• LogD (pH = 7.4): -0.40538698
• Log P: 2.8772032
• Molar Refractivity: 89.89 cm^3
• Polarizability: 35.992462 Å^3
• Polar Surface Area: 67.26 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T010070

Tazarotenic Acid Sulfoxide is the inactive sulfoxide metabolite of Tazarotenic Acid (T010060).

REFERENCES

• Cashman, J., et al.: Chem. Res. Toxicol., 8, 166 (1995)
• Mugford, C., et al.: Drug Metab. Rev., 30, 441 (1995)
• Marill, J., et al.: Biochem. Pharmacol., 63, 933 (1995)