(1S,2R,10R,11S,13R,15S)-13-fluoro-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-14-one

• ChemBase ID: 169056
• Molecular Formular: C19H27FO
• Molecular Mass: 290.4154832
• Monoisotopic Mass: 290.2045937
• SMILES: C1CCC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3C[C@H](C1=O)F)C
• Canonical SMILES: F[C@@H]1C[C@@H]2[C@](C1=O)(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CCCC2
• InChI: InChI=1S/C19H27FO/c1-18-9-4-3-5-12(18)6-7-13-14(18)8-10-19(2)15(13)11-16(20)17(19)21/h6,13-16H,3-5,7-11H2,1-2H3/t13-,14+,15+,16-,18+,19+/m1/s1
• InChIKey: VHZXNQKVFDBFIK-NBBHSKLNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,13R,15S)-13-fluoro-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-one
• IUPAC Traditional name: (1S,2R,10R,11S,13R,15S)-13-fluoro-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-one
• Synonyms: (16α)-Fluoro-5-androsten-17-one; Fluasterone

Database IDs

• CAS Number: 112859-71-9
• PubChem SID: 162263188
• PubChem CID: 133967

CALCULATED PROPERTIES

• Acid pKa: 16.482288
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.7684493
• LogD (pH = 7.4): 4.7684493
• Log P: 4.7684493
• Molar Refractivity: 82.7895 cm^3
• Polarizability: 32.317684 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F500300

A synthetic derivative of Dehydroepiandrosterone. The reduced androgenicity of Fluasterone may obviate toxicities associated with the androgenicity of the parent compound. Antitumor agent. Used in clinical trials for prostate cancer prevention.

REFERENCES

• Bentley, P., et al.: Food Chem. Toxicol., 31, 857 (1993)
• Rao, K., et al.: Cancer Res., 59, 3084 (1993)
• Masuzaki, H., et al.: Science, 294, 2166 (1993)
• Osawa, E., et al.: Life Sci., 70, 2623 (1993)