(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}-2-methylpropanoyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168923
• Molecular Formular: C29H42N2O10
• Molecular Mass: 578.65118
• Monoisotopic Mass: 578.28394555
• 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(C(=O)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(C(=O)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/C29H42N2O10/c1-27(2,26(39)41-25-21(35)19(33)20(34)22(40-25)24(37)38)31-23(36)16-7-6-14-13-5-8-17-29(4,12-10-18(32)30-17)15(13)9-11-28(14,16)3/h10,12-17,19-22,25,33-35H,5-9,11H2,1-4H3,(H,30,32)(H,31,36)(H,37,38)/t13-,14-,15-,16+,17+,19-,20-,21+,22-,25-,28-,29+/m0/s1
• InChIKey: XCAHIQQKLPVTDT-WQIHUYEGSA-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}-2-methylpropanoyl)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}-2-methylpropanoyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Finasteride Carboxylic Acid Acyl-β-D-glucuronide

Database IDs

• PubChem SID: 162263055
• PubChem CID: 71316738

CALCULATED PROPERTIES

• Acid pKa: 3.3137662
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -1.6502569
• LogD (pH = 7.4): -2.8788953
• Log P: 0.30679974
• Molar Refractivity: 141.9808 cm^3
• Polarizability: 56.722004 Å^3
• Polar Surface Area: 191.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F342010

A metabolite of Finasteride (F342000) in human bile (M3 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)