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

• ChemBase ID: 126516
• Molecular Formular: C21H27ClO3
• Molecular Mass: 362.89028
• Monoisotopic Mass: 362.1648724
• SMILES: O=C1C=C2C(=C[C@@H]3[C@H](CC[C@@]4([C@@](O)(C(=O)C)CC[C@@H]34)C)[C@@]2(C)CC1)Cl
• Canonical SMILES: O=C1CC[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/C21H27ClO3/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/h10-11,14-16,25H,4-9H2,1-3H3/t14-,15+,16+,19-,20+,21+/m1/s1
• InChIKey: VUHJZBBCZGVNDZ-TTYLFXKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-acetyl-8-chloro-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-5-one
• IUPAC Traditional name: chlormadinone
• Synonyms: 6-Chloro-17-hydroxypregna-4,6-diene-3,20-dione; 6-Chloro-6-dehydro-17-hydroxyprogesterone; 6-Chloro-6-dehydro-17-α-hydroxyprogesterone; Chlormadinon; Chlormadinone

Database IDs

• CAS Number: 1961-77-9
• PubChem SID: 162220849
• PubChem CID: 5284533
• ATC CODE: G03DB06
• Chemspider ID: 4447590
• Wikipedia Title: Chlormadinone

CALCULATED PROPERTIES

• Acid pKa: 12.6991005
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.2760208
• LogD (pH = 7.4): 3.2760186
• Log P: 3.2760208
• Molar Refractivity: 99.9381 cm^3
• Polarizability: 38.613174 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dioxane; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 196-199°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C343490

It has been used in combinations as an oral contraceptive.

REFERENCES

• Brennan, D.M., et al.: Acta Endocrinol., 44, 367 (1963)
• Honma., s., et al.: Chem Pharm. Bull., 25 2019 (1963)
• Usui, T., et al.: Acta Urol. Jpn., 27, 327 (1963)