(1S,2S,7S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.02,7.011,15]heptadec-13-en-5-one

• ChemBase ID: 177156
• Molecular Formular: C24H31NO
• Molecular Mass: 349.50904
• Monoisotopic Mass: 349.24056462
• SMILES: C1C(=O)C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=CC2)c1cccnc1)C)C
• Canonical SMILES: O=C1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC=C2c1cccnc1)C)C
• InChI: InChI=1S/C24H31NO/c1-23-11-9-18(26)14-17(23)5-6-19-21-8-7-20(16-4-3-13-25-15-16)24(21,2)12-10-22(19)23/h3-4,7,13,15,17,19,21-22H,5-6,8-12,14H2,1-2H3/t17-,19-,21-,22-,23-,24+/m0/s1
• InChIKey: FKNZCFYWNHCQGE-IRMBCWQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,7S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-13-en-5-one
• IUPAC Traditional name: (1S,2S,7S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-13-en-5-one
• Synonyms: (5α)-17-(3-Pyridinyl)androst-16-en-3-one

Database IDs

• CAS Number: 154229-26-2
• PubChem SID: 164233066
• PubChem CID: 11725391

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.5067554
• LogD (pH = 7.4): 4.5773735
• Log P: 4.578373
• Molar Refractivity: 105.4243 cm^3
• Polarizability: 41.435966 Å^3
• Polar Surface Area: 29.96 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P991665

(5α)-17-(3-Pyridinyl)androst-16-en-3-one is a related compound of Abiraterone (A108490). (5α)-17-(3-Pyridinyl)androst-16-en-3-one is a 17-(3-pyridyl)-substituted steroid useful in cancer treatment such as prostatic cancer and breast cancer.

REFERENCES

• Potter, G.A., et al.: J. Med. Chem., 38, 2463 (1995)