(1S,2R,5S,10R,11S,14R,15S)-14-(2H3)acetyl-8-chloro-5-hydroxy-2,15-dimethyl(4,4,5,6-2H4)tetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-14-yl acetate

• ChemBase ID: 164072
• Molecular Formular: C23H31ClO4
• Molecular Mass: 406.94284
• Monoisotopic Mass: 406.19108715
• SMILES: C1[C@@H](C=C2[C@](C1)([C@@H]1[C@@H](C=C2Cl)[C@H]2[C@](CC1)([C@](CC2)(C(=O)C)OC(=O)C)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=C1)C(=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(OC(=O)C)C(=O)C)C)Cl)C
• InChI: InChI=1S/C23H31ClO4/c1-13(25)23(28-14(2)26)10-7-18-16-12-20(24)19-11-15(27)5-8-21(19,3)17(16)6-9-22(18,23)4/h11-12,15-18,27H,5-10H2,1-4H3/t15-,16+,17-,18-,21+,22-,23-/m0/s1
• InChIKey: QQEHDZXXCDSAFE-JBSAMAPISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10R,11S,14R,15S)-14-(^2H₃)acetyl-8-chloro-5-hydroxy-2,15-dimethyl(4,4,5,6-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• IUPAC Traditional name: (1S,2R,5S,10R,11S,14R,15S)-14-(^2H₃)acetyl-8-chloro-5-hydroxy-2,15-dimethyl(4,4,5,6-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• Synonyms: (3β)-17-(Acetyloxy)-6-chloro-3-hydroxypregna-4,6-dien-20-one-d7; 17α-Acetoxy-6-chloro-3β-hydroxypregna-4,6-dien-20-one-d7; 3β-Hydroxychlormadinone Acetate-d7; 6-Chloro-3β,17-dihydroxypregna-4,6-dien-20-one 17-Acetate-d7; AY 11497-d7; Chlormadinol Acetate-d7

Database IDs

• PubChem SID: 162258207
• PubChem CID: 71314680

CALCULATED PROPERTIES

• Acid pKa: 14.856184
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.3058076
• LogD (pH = 7.4): 3.3058076
• Log P: 3.3058076
• Molar Refractivity: 109.987 cm^3
• Polarizability: 42.998615 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C343462

The labelled active metabolite of Chlormadinone acetate (CMA) (C343500).

REFERENCES

• Vaitukaitis, J., et al.: J. Clin. Endocrinol. Metab., 33, 988 (1971)
• Handy, R., et al.: Drug Metab. Disposition., 2, 214 (1971)
• Fiet, J., et al.: Steroids, 66, 609 (1971)