1-[(1S,2R,5S,10R,11S,14R,15S)-8-chloro-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-14-yl]ethan-1-one

• ChemBase ID: 164069
• Molecular Formular: C21H29ClO3
• Molecular Mass: 364.90616
• Monoisotopic Mass: 364.18052247
• SMILES: C1[C@@H](C=C2[C@](C1)([C@@H]1[C@@H](C=C2Cl)[C@H]2[C@](CC1)([C@@](CC2)(O)C(=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(O)C(=O)C)C)Cl)C
• InChI: InChI=1S/C21H29ClO3/c1-12(23)21(25)9-6-16-14-11-18(22)17-10-13(24)4-7-19(17,2)15(14)5-8-20(16,21)3/h10-11,13-16,24-25H,4-9H2,1-3H3/t13-,14+,15-,16-,19+,20-,21-/m0/s1
• InChIKey: WZTUZRFSDWXDRM-IAGOJMRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2R,5S,10R,11S,14R,15S)-8-chloro-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl]ethan-1-one
• IUPAC Traditional name: 1-[(1S,2R,5S,10R,11S,14R,15S)-8-chloro-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl]ethanone
• Synonyms: (3β)-6-Chloro-3,17-dihydroxypregna-4,6-dien-20-one; 6-Chloro-3β,17-dihydroxypregna-4,6-dien-20-one; Clogestone; Chlormadinol

Database IDs

• CAS Number: 20047-75-0
• PubChem SID: 162258204
• PubChem CID: 20055454

CALCULATED PROPERTIES

• H Donor: 2
• LogD (pH = 5.5): 2.8646822
• LogD (pH = 7.4): 2.86468
• Log P: 2.8646822
• Molar Refractivity: 100.8355 cm^3
• Polarizability: 39.15732 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 12.696089
• H Acceptors: 3

DETAILS

Toronto Research Chemicals - C343450

Hormonal contraceptive.

REFERENCES

• Zacharias, S., et al.: Contraception, 33, 203 ( 1986),