(1S,2S,10R,11S,14R,15S)-14-(2H3)acetyl-8-chloro-14-hydroxy-2,15-dimethyl(4,6-2H2)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6,8-trien-5-one

• ChemBase ID: 165725
• Molecular Formular: C21H25ClO3
• Molecular Mass: 360.8744
• Monoisotopic Mass: 360.14922234
• SMILES: C1=C[C@]2(C(=CC1=O)C(=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)Cl)C
• Canonical SMILES: O=C1C=C[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/C21H25ClO3/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/h4,7,10-11,14-16,25H,5-6,8-9H2,1-3H3/t14-,15+,16+,19-,20+,21+/m1/s1
• InChIKey: ZSAMZEYLGUEVJW-TTYLFXKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,10R,11S,14R,15S)-14-(^2H₃)acetyl-8-chloro-14-hydroxy-2,15-dimethyl(4,6-^2H₂)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,8-trien-5-one
• IUPAC Traditional name: (1S,2S,10R,11S,14R,15S)-14-(^2H₃)acetyl-8-chloro-14-hydroxy-2,15-dimethyl(4,6-^2H₂)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,8-trien-5-one
• Synonyms: 6-Chloro-17-hydroxypregna-1,4,6-triene-3,20-dione-d5; Δ1-Chlormadinone-d5; Delmadinone-d5

Database IDs

• PubChem SID: 162259858
• PubChem CID: 71315362

CALCULATED PROPERTIES

• Acid pKa: 12.6991
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.2738442
• LogD (pH = 7.4): 3.273842
• Log P: 3.2738442
• Molar Refractivity: 101.0314 cm^3
• Polarizability: 38.368828 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D230657

Labelled Delmadinone (D230655). Progesterone with antiestrogen and antiandrogen activity.

REFERENCES

• Brown-Grant, K., et al.: J. Endocrinol., 38, 145 (1967)
• Ferraresi, R., et al.: J. Allergy Clin. Immunol., 55, 25 (1967)