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

• ChemBase ID: 158814
• Molecular Formular: C26H33NO2
• Molecular Mass: 391.54572
• Monoisotopic Mass: 391.2511293
• SMILES: C1[C@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC=C1c1cccnc1)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC=C2c2cccnc2)C)C1)C
• InChI: InChI=1S/C26H33NO2/c1-17(28)29-20-10-12-25(2)19(15-20)6-7-21-23-9-8-22(18-5-4-14-27-16-18)26(23,3)13-11-24(21)25/h4-6,8,14,16,20-21,23-24H,7,9-13,15H2,1-3H3/t20-,21+,23+,24+,25+,26-/m1/s1
• InChIKey: UVIQSJCZCSLXRZ-BRSOJCHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5R,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,13-dien-5-yl acetate
• IUPAC Traditional name: (1S,2R,5R,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,13-dien-5-yl acetate
• Synonyms: (3β)-17-(3-Pyridinyl)androsta-5,16-dien-3-ol Acetate (Ester); CB 7630; Abiraterone Acetate

Database IDs

• CAS Number: 154229-18-2
• PubChem SID: 162252949
• PubChem CID: 71312699

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.3348007
• LogD (pH = 7.4): 4.405419
• Log P: 4.4064183
• Molar Refractivity: 116.4539 cm^3
• Polarizability: 45.55833 Å^3
• Polar Surface Area: 39.19 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 127-130°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A108500

Abiraterone acetate is a novel steroidal inhibitor of human Cytochrome P450 (17α-Hydroxylase-C17,20-lyase): potential agent for the treatment of prostatic cancer.

REFERENCES

• Denis, L., et al.: Cancer, 72, 3888 (1993)
• Potter, G.A., et al.: J. Med. Chem., 38, 2463 (1993)
• Denmeade, S., et al.: Nat. Rev., 2, 389(1993)
• Scher, H., et al.: J. Clin. Oncol., 23, 8253 (1993)