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

• ChemBase ID: 173892
• Molecular Formular: C25H34O4
• Molecular Mass: 398.53506
• Monoisotopic Mass: 398.24570957
• SMILES: [C@@]12(C(=CC(=O)[C@H](C2)C)C(=C[C@@H]2[C@@H]1CC[C@]1([C@H]2CC[C@]1(OC(=O)C)C(=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@H](C[C@]12C)C)C)C(=O)C
• InChI: InChI=1S/C25H34O4/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/h11-12,15,18-20H,7-10,13H2,1-6H3/t15-,18+,19-,20-,23+,24-,25-/m0/s1
• InChIKey: AQMUMBCTNJGBGC-UFNWQTQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4S,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-6,8-dien-14-yl acetate
• IUPAC Traditional name: (1S,2R,4S,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-6,8-dien-14-yl acetate
• Synonyms: (2β)-17-(Acetyloxy)-2,6-dimethylpregna-4,6-diene-3,20-dione; (2β)-Methyl Megestrol Acetate

Database IDs

• PubChem SID: 164229802
• PubChem CID: 29983910

CALCULATED PROPERTIES

• Acid pKa: 17.829681
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.266731
• LogD (pH = 7.4): 4.266731
• Log P: 4.266731
• Molar Refractivity: 113.2299 cm^3
• Polarizability: 44.28529 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 to Pale Yellow
• Melting Point: 196-199°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M320245

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)