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

• ChemBase ID: 173675
• Molecular Formular: C24H32O4
• Molecular Mass: 384.50848
• Monoisotopic Mass: 384.2300595
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2=C)[C@H]2[C@](CC1)([C@@](CC2)(OC(=O)C)C(=O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C(=C)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/C24H32O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h13,18-20H,1,6-12H2,2-5H3/t18-,19+,20+,22-,23+,24+/m1/s1
• InChIKey: YCDZXIYKJHQMIG-GQFGMJRRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-acetyl-2,15-dimethyl-8-methylidene-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-14-acetyl-2,15-dimethyl-8-methylidene-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• Synonyms: 17-(Acetyloxy)-6-methylenepregn-4-ene-3,20-dione; 17-Hydroxy-6-methylenepregn-4-ene-3,20-dione Acetate; 17-Hydroxy-6-methyleneprogesterone Acetate; 17-Acetoxy-6-methylenepregn-4-ene-3,20-dione; 17α-Acetoxy-6-methylenepregn-4-ene-3,20-dione; 17α-Acetoxy-6-methyleneprogesterone; 6,6'-Dehydromedroxyprogesterone Acetate; NSC 58799; 6-Methylene Progesterone Acetate

Database IDs

• CAS Number: 32634-95-0
• PubChem SID: 164229585
• PubChem CID: 94436

CALCULATED PROPERTIES

• Acid pKa: 17.826317
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.781678
• LogD (pH = 7.4): 3.781678
• Log P: 3.781678
• Molar Refractivity: 107.5829 cm^3
• Polarizability: 42.444622 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M304220

6-Methylene Progesterone Acetate is an impurity of Medroxyprogesterone 17-Acetate (M203560). Medroxyprogesterone 17-Acetate impurity F as per EP.

REFERENCES

• Krischenowski, D., et al.: Steroids, 58, 278 (1993)
• Bratoeff, E., et al.: Chem. Pharm. Bull., 51, 1132 (1993)