(1S,2R,10R,11S,14R,15S)-14-acetyl-8-chloro-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6,8-trien-14-yl acetate

• ChemBase ID: 126885
• Molecular Formular: C23H27ClO4
• Molecular Mass: 402.91108
• Monoisotopic Mass: 402.15978702
• SMILES: O=C1C=C[C@]2(C(=C1)C(=C[C@@H]1[C@@H]2CC[C@@]2([C@@](OC(=O)C)(C(=O)C)CC[C@@H]12)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(OC(=O)C)C(=O)C)C)Cl)C
• InChI: InChI=1S/C23H27ClO4/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/h5,8,11-12,16-18H,6-7,9-10H2,1-4H3/t16-,17+,18+,21-,22+,23+/m1/s1
• InChIKey: CGBCCZZJVKUAMX-DFXBJWIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-acetyl-8-chloro-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,8-trien-14-yl acetate
• IUPAC Traditional name: tardak
• Synonyms: Delmadinone acetate; 17-(Acetyloxy)-6-chloropregna-1,4,6-triene-3,20-dione; 17-Acetoxy-6-chloropregna-1,4,6-triene-3,20-dione; 17α-Acetoxy-6-chloropregna-1,4,6-triene-3,20-dione; 6-Chloro-17-hydroxypregna-1,4,6-triene-3,20-dione Acetate; Delminal; Estrex; RS 1301; Tardastrex; Tarden; Zenadrex; Δ1-Chlormadinone Acetate

Database IDs

• CAS Number: 13698-49-2
• PubChem SID: 162221211
• PubChem CID: 10135765
• ATC CODE: QG03DX91
• Chemspider ID: 8311278
• Wikipedia Title: Delmadinone_acetate

CALCULATED PROPERTIES

• Acid pKa: 17.829681
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.7149696
• LogD (pH = 7.4): 3.7149696
• Log P: 3.7149696
• Molar Refractivity: 110.1829 cm^3
• Polarizability: 42.21056 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Tan Solid
• Melting Point: 167-170°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D230665

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)