(2S,3S,4S,5R,6S)-6-[(2-{[(1S,2R,7R,10S,11S,14S,15S)-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.02,7.011,15]heptadec-3-en-14-yl]formamido}propan-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168958
• Molecular Formular: C28H42N2O9
• Molecular Mass: 550.64108
• Monoisotopic Mass: 550.28903093
• SMILES: C1=CC(=O)N[C@H]2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)C(=O)NC(O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)(C)C)C)C
• Canonical SMILES: O=C1C=C[C@]2([C@H](N1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)NC(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)(C)C)C)C
• InChI: InChI=1S/C28H42N2O9/c1-26(2,39-25-21(34)19(32)20(33)22(38-25)24(36)37)30-23(35)16-7-6-14-13-5-8-17-28(4,12-10-18(31)29-17)15(13)9-11-27(14,16)3/h10,12-17,19-22,25,32-34H,5-9,11H2,1-4H3,(H,29,31)(H,30,35)(H,36,37)/t13-,14-,15-,16+,17+,19-,20-,21+,22-,25-,27-,28+/m0/s1
• InChIKey: CSYHGUBQVUIUAW-SXOJUZMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(2-{[(1S,2R,7R,10S,11S,14S,15S)-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-en-14-yl]formamido}propan-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(2-{[(1S,2R,7R,10S,11S,14S,15S)-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-en-14-yl]formamido}propan-2-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Finasteride 2-(2-Methylpropanol)amide β-D-Glucuronide

Database IDs

• PubChem SID: 162263090
• PubChem CID: 71316753

CALCULATED PROPERTIES

• Acid pKa: 3.3940046
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -1.6526194
• LogD (pH = 7.4): -2.944431
• Log P: 0.25127533
• Molar Refractivity: 137.637 cm^3
• Polarizability: 54.761364 Å^3
• Polar Surface Area: 174.65 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F342025

A metabolite of Finasteride (F342000) in human bile (M1 glucuronide).

REFERENCES

• Faller, B., et al.: Biochemistry, 32, 5705 (1993)
• Carlin, J.R., Drug Metab. Dispos., 25, 100 (1993)
• Bergman, E., et al.: Eur. J. Pharm. Sci., 29, 205 (1993)