(1S,2R,7R,10S,11S,14S,15S)-2,15-dimethyl-N-(2-methyl-1-oxopropan-2-yl)-5-oxo-6-azatetracyclo[8.7.0.02,7.011,15]heptadec-3-ene-14-carboxamide

• ChemBase ID: 168922
• Molecular Formular: C23H34N2O3
• Molecular Mass: 386.52766
• Monoisotopic Mass: 386.25694296
• 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)(C)C=O)C)C
• Canonical SMILES: O=CC(NC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)C=CC(=O)N2)(C)C
• InChI: InChI=1S/C23H34N2O3/c1-21(2,13-26)25-20(28)17-7-6-15-14-5-8-18-23(4,12-10-19(27)24-18)16(14)9-11-22(15,17)3/h10,12-18H,5-9,11H2,1-4H3,(H,24,27)(H,25,28)/t14-,15-,16-,17+,18+,22-,23+/m0/s1
• InChIKey: GWKLHNVFRBYLTN-WSBQPABSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,7R,10S,11S,14S,15S)-2,15-dimethyl-N-(2-methyl-1-oxopropan-2-yl)-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-14-carboxamide
• IUPAC Traditional name: (1S,2R,7R,10S,11S,14S,15S)-2,15-dimethyl-N-(2-methyl-1-oxopropan-2-yl)-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-14-carboxamide
• Synonyms: (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(1,1-Dimethyl-2-oxoethyl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxamide; Finasteride-ω-al; Finasteride Carboxaldehyde

Database IDs

• CAS Number: 154387-61-8
• PubChem SID: 162263054
• PubChem CID: 15230774

CALCULATED PROPERTIES

• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 13.269881
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.34024
• LogD (pH = 7.4): 2.3404465
• Log P: 2.3404496
• Molar Refractivity: 108.7568 cm^3
• Polarizability: 42.427856 Å^3
• Polar Surface Area: 75.27 Å^2

DETAILS

Toronto Research Chemicals - F342005

A metabolite of Finasteride (F342000) in human bile (M2 metabolite).

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)