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

• ChemBase ID: 164074
• Molecular Formular: C23H29ClO4
• Molecular Mass: 404.92696
• Monoisotopic Mass: 404.17543709
• SMILES: C1C(=O)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
• Canonical SMILES: O=C1CC[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/C23H29ClO4/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/h11-12,16-18H,5-10H2,1-4H3/t16-,17+,18+,21-,22+,23+/m1/s1
• InChIKey: QMBJSIBWORFWQT-DFXBJWIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-(^2H₃)acetyl-8-chloro-2,15-dimethyl-5-oxo(4,4,6-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-14-(^2H₃)acetyl-8-chloro-2,15-dimethyl-5-oxo(4,4,6-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• Synonyms: 17-(Acetyloxy)-6-chloropregna-4,6-diene-3,20-dione-d6; 17-Acetoxy-6-chloro-6-dehydroprogesterone-d6; 6-Chloro-17-acetoxy-4,6-pregnadiene-3,20-dione-d6; Chronosyn-d6; Fertiletten-d6; Chlormadinone-d6 Acetate

Database IDs

• PubChem SID: 162258209
• PubChem CID: 71314682

CALCULATED PROPERTIES

• Acid pKa: 17.825098
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.7171462
• LogD (pH = 7.4): 3.7171462
• Log P: 3.7171462
• Molar Refractivity: 109.0896 cm^3
• Polarizability: 42.455414 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 197-199°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C343502

Orally active progesteron with antiandrogenic activity; has been used in combinations as an oral contraceptive. Progestogen; antineoplastic (hormonal).

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)