6-{2-[4,4-bis(2H3)methyl-3,4-dihydro-2H-1-benzothiopyran-6-yl]ethynyl}pyridine-3-carboxylic acid

• ChemBase ID: 178097
• Molecular Formular: C19H17NO2S
• Molecular Mass: 323.40878
• Monoisotopic Mass: 323.09799979
• SMILES: C1CSc2c(C1(C)C)cc(cc2)C#Cc1ncc(cc1)C(=O)O
• Canonical SMILES: OC(=O)c1ccc(nc1)C#Cc1ccc2c(c1)C(C)(C)CCS2
• InChI: InChI=1S/C19H17NO2S/c1-19(2)9-10-23-17-8-4-13(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: IQIBKLWBVJPOQO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-{2-[4,4-bis(^2H₃)methyl-3,4-dihydro-2H-1-benzothiopyran-6-yl]ethynyl}pyridine-3-carboxylic acid
• IUPAC Traditional name: 6-{2-[4,4-bis(^2H₃)methyl-2,3-dihydro-1-benzothiopyran-6-yl]ethynyl}pyridine-3-carboxylic acid
• Synonyms: 6-[2-(3,4-Dihydro-4,4-(dimethyl-d6)-2H-1-benzothiopyran-6-yl-d2)ethynyl]-3-pyridinecarboxylic Acid; AGN 190299-d8; Tazarotenic Acid-d8

Database IDs

• PubChem SID: 164234007
• PubChem CID: 71752333

CALCULATED PROPERTIES

• Acid pKa: 3.7620583
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.7699814
• LogD (pH = 7.4): 1.2334486
• Log P: 4.5160384
• Molar Refractivity: 88.3643 cm^3
• Polarizability: 35.360546 Å^3
• Polar Surface Area: 50.19 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T010062

Labelled Tazarotenic Acid (T010060). Tazarotenic acid is the major active metabolite of Tazarotene (T010050).

REFERENCES

• Nagpal, S., et al.: J. Biol. Chem., 270, 923 (1995)
• Madhu, C., et al.: J. Pharm. Sci., 86, 972 (1995)
• Attar, M., et al.: Drug Metab. Dispos., 31, 476 (1995)