(1S,2R,8R,10R,11S,14R,15S)-14-acetyl-8-hydroxy-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl acetate

• ChemBase ID: 170721
• Molecular Formular: C24H34O5
• Molecular Mass: 402.52376
• Monoisotopic Mass: 402.24062419
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](C[C@]2(O)C)[C@H]2[C@](CC1)([C@](CC2)(C(=O)C)OC(=O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)[C@](C)(O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(OC(=O)C)C(=O)C)C)C
• InChI: InChI=1S/C24H34O5/c1-14(25)24(29-15(2)26)11-8-19-17-13-23(5,28)20-12-16(27)6-9-21(20,3)18(17)7-10-22(19,24)4/h12,17-19,28H,6-11,13H2,1-5H3/t17-,18+,19+,21-,22+,23-,24+/m1/s1
• InChIKey: BIIFPBLHBAQCTJ-MCLNPTNPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8R,10R,11S,14R,15S)-14-acetyl-8-hydroxy-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: (1S,2R,8R,10R,11S,14R,15S)-14-acetyl-8-hydroxy-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• Synonyms: (6β)-17-(Acetyloxy)-6-hydroxy-6-methylpregn-4-ene-3,20-dione; 6β,17-Dihydroxy-6-methylpregn-4-ene-3,20-dione 17-Acetate; 6β-Hydroxymedroxyprogesterone 17-Acetate; 6β-Hydroxy Medroxy Progesterone 17-Acetate

Database IDs

• CAS Number: 984-47-4
• PubChem SID: 164226631
• PubChem CID: 71749110

CALCULATED PROPERTIES

• Acid pKa: 14.379707
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.8920703
• LogD (pH = 7.4): 2.8920703
• Log P: 2.8920703
• Molar Refractivity: 109.4105 cm^3
• Polarizability: 43.32088 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H944505

6β-Hydroxy Medroxy Progesterone 17-Acetate is a major metabolite of Medroxyprogesterone 17-Acetate (M203560) as well as an impurity of Megestrol Acetate (M208050).

REFERENCES

• Chen, J. et al.: Chem. Pharnac. Bull., 57, 835 (2009)
• Zhang J.-W. et al.: Drug Metab. Dispos., 36, 2292 (2009)
• Fang, X.G. et al.: Acta Pharm. Sin., 21, 613 (2009)