(1S,2S,10R,11S,14R,15S)-14-acetyl-2,4,8,15-tetramethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6,8-trien-14-yl acetate

• ChemBase ID: 173894
• Molecular Formular: C25H32O4
• Molecular Mass: 396.51918
• Monoisotopic Mass: 396.2300595
• SMILES: [C@@]12(C(=CC(=O)C(=C2)C)C(=C[C@@H]2[C@@H]1CC[C@]1([C@H]2CC[C@@]1(C(=O)C)OC(=O)C)C)C)C
• Canonical SMILES: CC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C=C(C2=CC(=O)C(=C[C@]12C)C)C)C(=O)C
• InChI: InChI=1S/C25H32O4/c1-14-11-18-19(23(5)13-15(2)22(28)12-21(14)23)7-9-24(6)20(18)8-10-25(24,16(3)26)29-17(4)27/h11-13,18-20H,7-10H2,1-6H3/t18-,19+,20+,23-,24+,25+/m1/s1
• InChIKey: DBRWQZMZXVVIKF-DAHGFBLPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,10R,11S,14R,15S)-14-acetyl-2,4,8,15-tetramethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,8-trien-14-yl acetate
• IUPAC Traditional name: (1S,2S,10R,11S,14R,15S)-14-acetyl-2,4,8,15-tetramethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6,8-trien-14-yl acetate
• Synonyms: Megestrol Acetate Impurity; 2-Methyl-Δ1-megestrol Acetate (Megestrol Acetate Impurity)

Database IDs

• PubChem SID: 164229804
• PubChem CID: 29983912

CALCULATED PROPERTIES

• Acid pKa: 17.829681
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.1171184
• LogD (pH = 7.4): 4.1171184
• Log P: 4.1171184
• Molar Refractivity: 114.1058 cm^3
• Polarizability: 44.043472 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid
• Melting Point: 227-229°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M320260

A related impurity in Megestrol acetate (M208050).

REFERENCES

• Schneider, F., et al.: Helv. Chim. Acta, 56, 2396 (1973)
• Aisner, J., et al.: Semin. Oncol., 15, 68 (1973)
• Krischenowski, D., et al.: Steroids, 58, 278 (1973)
• Bratoeff, E., et al.: Chem. Pharm. Bull., 51, 1132 (1973)