(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-2,16-dimethyl-6,9-dioxopentacyclo[9.7.0.02,8.03,5.012,16]octadec-7-en-15-yl acetate

• ChemBase ID: 172059
• Molecular Formular: C24H30O5
• Molecular Mass: 398.492
• Monoisotopic Mass: 398.20932406
• SMILES: [C@H]12[C@H](C(=O)C=C3[C@]1([C@@H]1[C@@H](CC3=O)[C@H]3[C@](CC1)([C@@](CC3)(OC(=O)C)C(=O)C)C)C)C2
• Canonical SMILES: CC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC(=O)C2=CC(=O)[C@H]3[C@@H]([C@]12C)C3)C(=O)C
• InChI: InChI=1S/C24H30O5/c1-12(25)24(29-13(2)26)8-6-16-14-10-21(28)19-11-20(27)15-9-18(15)23(19,4)17(14)5-7-22(16,24)3/h11,14-18H,5-10H2,1-4H3/t14-,15+,16-,17-,18-,22-,23-,24-/m0/s1
• InChIKey: WIRUTYUSQYFQAC-FDTZYFLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-2,16-dimethyl-6,9-dioxopentacyclo[9.7.0.0^2,^8.0^3,^5.0^1^2,^1^6]octadec-7-en-15-yl acetate
• IUPAC Traditional name: (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-2,16-dimethyl-6,9-dioxopentacyclo[9.7.0.0^2,^8.0^3,^5.0^1^2,^1^6]octadec-7-en-15-yl acetate
• Synonyms: 1β,2β-Dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4-diene-3,6,20-trione Acetate; 6-Keto Cyproterone Acetate

Database IDs

• CAS Number: 17184-05-3
• PubChem SID: 164227969
• PubChem CID: 71749674

CALCULATED PROPERTIES

• Acid pKa: 17.828089
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.0967321
• LogD (pH = 7.4): 3.0967321
• Log P: 3.0967321
• Molar Refractivity: 106.6699 cm^3
• Polarizability: 42.055782 Å^3
• Polar Surface Area: 77.51 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K187650

An impurity of Cyproterone acetate (C989100), a new antiandrogenic steroid.

REFERENCES

• Wiechert, R., et al.: Arzneim.Forsch., 17 1103 (1967)