(1S,2S,3S,5R,9R,11S,12R,13S,16R,17S)-16-acetyl-2,17-dimethyl-6-oxo-10-oxahexacyclo[10.7.0.02,8.03,5.09,11.013,17]nonadec-7-en-16-yl acetate

• ChemBase ID: 166070
• 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]([C@H]4[C@@H]3O4)[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]2[C@@H]2O[C@@H]2C2=CC(=O)[C@H]3[C@@H]([C@]12C)C3)C(=O)C
• InChI: InChI=1S/C24H30O5/c1-11(25)24(29-12(2)26)8-6-14-19-15(5-7-22(14,24)3)23(4)16-9-13(16)18(27)10-17(23)20-21(19)28-20/h10,13-16,19-21H,5-9H2,1-4H3/t13-,14+,15+,16+,19+,20-,21+,22+,23+,24+/m1/s1
• InChIKey: XFELGPWPVWOTLJ-IWMHJGDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3S,5R,9R,11S,12R,13S,16R,17S)-16-acetyl-2,17-dimethyl-6-oxo-10-oxahexacyclo[10.7.0.0^2,^8.0^3,^5.0^9,^1^1.0^1^3,^1^7]nonadec-7-en-16-yl acetate
• IUPAC Traditional name: (1S,2S,3S,5R,9R,11S,12R,13S,16R,17S)-16-acetyl-2,17-dimethyl-6-oxo-10-oxahexacyclo[10.7.0.0^2,^8.0^3,^5.0^9,^1^1.0^1^3,^1^7]nonadec-7-en-16-yl acetate
• Synonyms: (1β,2β,6α,7α)-17-(Acetyloxy)-6,7-epoxy-1,2-dihydro-3'H-cyclopropa[1,2]pregna-1,4-diene-3,20-dione; 6α,7α-Epoxy-1β,2β-dihydro-17-hydroxy-3'H-cyclopropa[1,2]pregna-1,4-diene-3,20-dione Acetate; 6-Deschloro-6,7-epoxy Cyproterone Acetate

Database IDs

• CAS Number: 15423-97-9
• PubChem SID: 162260203
• PubChem CID: 13423625

CALCULATED PROPERTIES

• Acid pKa: 17.465479
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.6979582
• LogD (pH = 7.4): 2.6979582
• Log P: 2.6979582
• Molar Refractivity: 105.2666 cm^3
• Polarizability: 41.949455 Å^3
• Polar Surface Area: 72.97 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288530

An impurity of Cyproterone acetate (C989100).

REFERENCES

• Shapiro, E., et al.: J. Med. Chem., 12, 631 (1969)
• Centurion, O., et al.: Steroids, 60, 434 (1969)