(2R,7R,10S,11S,14R,15S)-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.02,7.011,15]heptadec-3-ene-14-carboxylic acid

• ChemBase ID: 175988
• Molecular Formular: C19H27NO3
• Molecular Mass: 317.42258
• Monoisotopic Mass: 317.19909373
• SMILES: C1=CC(=O)N[C@H]2[C@]1(C1[C@@H](CC2)[C@H]2[C@](CC1)([C@@H](CC2)C(=O)O)C)C
• Canonical SMILES: O=C1C=C[C@]2([C@H](N1)CC[C@@H]1C2CC[C@]2([C@H]1CC[C@H]2C(=O)O)C)C
• InChI: InChI=1S/C19H27NO3/c1-18-9-7-13-11(12(18)4-5-14(18)17(22)23)3-6-15-19(13,2)10-8-16(21)20-15/h8,10-15H,3-7,9H2,1-2H3,(H,20,21)(H,22,23)/t11-,12-,13?,14-,15+,18-,19+/m0/s1
• InChIKey: FDESQZBVTKLIQN-JOVRCNNESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,7R,10S,11S,14R,15S)-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-14-carboxylic acid
• IUPAC Traditional name: (2R,7R,10S,11S,14R,15S)-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-14-carboxylic acid
• Synonyms: (4aR,4bS,6aS,7S,9aS,9bS,11aR)-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-carboxylic Acid Methyl Ester; (5α,17β)-3-oxo-4-Azaandrost-1-ene-17-carboxylic Acid Methyl Ester; 3-Oxo-4-aza-5α-αndrost-1-ene-17β-carboxylic Acid

Database IDs

• CAS Number: 104239-97-6
• PubChem SID: 164231898
• PubChem CID: 71751365

CALCULATED PROPERTIES

• Acid pKa: 4.763373
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.7926182
• LogD (pH = 7.4): 0.016504638
• Log P: 2.602819
• Molar Refractivity: 87.6715 cm^3
• Polarizability: 34.295666 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol; n-Propanol
• Apperance: Off-White Solid
• Melting Point: >260°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - O847250

A novel intermediate in the synthesis of Finasteride, a 5α-reductase inhibitor used for treatment of benign prostatic hyperplasia acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrogenetic related disorders.

REFERENCES

• Bakshi., et al.: J. Med. Chem., 38, 3189 (1995)