(1S,2S,3S,5R,11R,12S,13R,15R,16S)-15-acetyl-9-chloro-13-hydroxy-2,16-dimethyl-6-oxopentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-15-yl acetate

• ChemBase ID: 170175
• Molecular Formular: C24H29ClO5
• Molecular Mass: 432.93706
• Monoisotopic Mass: 432.17035171
• SMILES: [C@H]12[C@H](C(=O)C=C3[C@]1([C@@H]1[C@@H](C=C3Cl)[C@H]3[C@](CC1)([C@](C[C@H]3O)(C(=O)C)OC(=O)C)C)C)C2
• Canonical SMILES: CC(=O)O[C@@]1(C[C@H]([C@@H]2[C@]1(C)CC[C@H]1[C@H]2C=C(C2=CC(=O)[C@H]3[C@@H]([C@]12C)C3)Cl)O)C(=O)C
• InChI: InChI=1S/C24H29ClO5/c1-11(26)24(30-12(2)27)10-20(29)21-14-8-18(25)17-9-19(28)13-7-16(13)23(17,4)15(14)5-6-22(21,24)3/h8-9,13-16,20-21,29H,5-7,10H2,1-4H3/t13-,14-,15+,16+,20-,21-,22+,23+,24+/m1/s1
• InChIKey: HRANPRDGABOKNQ-ORGXEYTDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3S,5R,11R,12S,13R,15R,16S)-15-acetyl-9-chloro-13-hydroxy-2,16-dimethyl-6-oxopentacyclo[9.7.0.0^2,^8.0^3,^5.0^1^2,^1^6]octadeca-7,9-dien-15-yl acetate
• IUPAC Traditional name: (1S,2S,3S,5R,11R,12S,13R,15R,16S)-15-acetyl-9-chloro-13-hydroxy-2,16-dimethyl-6-oxopentacyclo[9.7.0.0^2,^8.0^3,^5.0^1^2,^1^6]octadeca-7,9-dien-15-yl acetate
• Synonyms: (1β,2β,15β)-17-(Acetyloxy)-6-chloro-1,2-dihydro-15-hydroxy-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione; 15β-Hydroxy Cyproterone Acetate

Database IDs

• CAS Number: 65423-26-9
• PubChem SID: 164226085
• PubChem CID: 163085

CALCULATED PROPERTIES

• Acid pKa: 14.793403
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.2572982
• LogD (pH = 7.4): 2.2572982
• Log P: 2.2572982
• Molar Refractivity: 113.3584 cm^3
• Polarizability: 44.22081 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate

DETAILS

Toronto Research Chemicals - H825160

Metabolite of Cyproterone Acetate

REFERENCES

• Kuhnz, W., et al.: Eur. J. Clin. Pharmacol., 53, 75 (1997)
• Lewis, D., et al.: J. Steroid Biochem. Mol. Biol., 74, 179 (1997)