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

• ChemBase ID: 164078
• Molecular Formular: C23H31ClO4
• Molecular Mass: 406.94284
• Monoisotopic Mass: 406.19108715
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](C[C@@H]2Cl)[C@H]2[C@](CC1)([C@@](CC2)(OC(=O)C)C(=O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)[C@@H](Cl)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(OC(=O)C)C(=O)C)C)C
• InChI: InChI=1S/C23H31ClO4/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/h11,16-18,20H,5-10,12H2,1-4H3/t16-,17+,18+,20+,21-,22+,23+/m1/s1
• InChIKey: DCVGANSDLNPXGO-WXLIAARGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10R,11S,14R,15S)-14-acetyl-8-chloro-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: hydromadinone acetate
• Synonyms: (6β)-17-(Acetyloxy)-6-chloropregn-4-ene-3,20-dione; 6β-Chloro-17-hydroxypregn-4-ene-3,20-dione Acetate; 6β-Chloro-17-hydroxyprogesterone Acetate; 6β-Chloro-17-acetoxy Progesterone; (6α)-17-(Acetyloxy)-6-chloropregn-4-ene-3,20-dione; 6α-Chloro-17-hydroxypregn-4-ene-3,20-dione Acetate; 6α-Chloro-17-hydroxyprogesterone Acetate; Hydromadinone Acetate; NSC 33170; 6α-Chloro-17-acetoxy Progesterone(Contain ~10% 6-β isomer)

Database IDs

• CAS Number: 2477-73-8; 2658-74-4
• PubChem SID: 162258213
• PubChem CID: 200665

CALCULATED PROPERTIES

• Acid pKa: 16.157812
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.9660854
• LogD (pH = 7.4): 3.9660854
• Log P: 3.9660854
• Molar Refractivity: 107.8233 cm^3
• Polarizability: 42.691822 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C363280

Progesterone (P755900) impurity.

Toronto Research Chemicals - C363285

Progesterone (P755900) impurity.

REFERENCES

• Liang, T., et al.: Biol. Chem., 256, 7998 (1981)
• Bratoeff, E., et al.: J. Steroid Biochem. Mol. Biol., 111, 275 (1981)
• Liang, T., et al.: Biol. Chem., 256, 7998 (1981)
• Bratoeff, E., et al.: J. Steroid Biochem. Mol. Biol., 111, 275 (1981)