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

• ChemBase ID: 166068
• Molecular Formular: C24H30O4
• Molecular Mass: 382.4926
• Monoisotopic Mass: 382.21440944
• SMILES: [C@H]12[C@H](C(=O)C=C3[C@]1([C@@H]1[C@@H](C=C3)[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]2C=CC2=CC(=O)[C@H]3[C@@H]([C@]12C)C3)C(=O)C
• InChI: InChI=1S/C24H30O4/c1-13(25)24(28-14(2)26)10-8-18-16-6-5-15-11-21(27)17-12-20(17)23(15,4)19(16)7-9-22(18,24)3/h5-6,11,16-20H,7-10,12H2,1-4H3/t16-,17+,18-,19-,20-,22-,23-,24-/m0/s1
• InChIKey: ARUYPSAYKHCXNE-UQNNAPNASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-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,15R,16S)-15-acetyl-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)-17-(Acetyloxy)-1,2-dihydro-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione; 17-Hydroxy-1α,2α-methylenepregna-4,6-diene-3,20-dione Acetate; 6-Deschloro Cyproterone Acetate

Database IDs

• CAS Number: 2701-50-0
• PubChem SID: 162260201
• PubChem CID: 13519086

CALCULATED PROPERTIES

• Acid pKa: 17.829681
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.402094
• LogD (pH = 7.4): 3.402094
• Log P: 3.402094
• Molar Refractivity: 107.0933 cm^3
• Polarizability: 41.7186 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288520

An impurity of Cyproterone acetate (C989100).

REFERENCES

• Shapiro, E., et al.: J. Med. Chem., 12, 631 (1969)
• Shibata, K., et al.: Chem. Pharm. Bull., 40, 935 (1969)
• Centurion, O., et al.: Steroids, 60, 434 (1969)