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

• ChemBase ID: 171092
• Molecular Formular: C24H34O5
• Molecular Mass: 402.52376
• Monoisotopic Mass: 402.24062419
• SMILES: [C@@]12(C(=CC(=O)CC2)C(C[C@@H]2[C@@H]1CC[C@]1([C@H]2CC[C@@]1(C(=O)C)OC(=O)C)C)CO)C
• Canonical SMILES: OCC1C[C@@H]2[C@@H]([C@@]3(C1=CC(=O)CC3)C)CC[C@]1([C@H]2CC[C@]1(OC(=O)C)C(=O)C)C
• InChI: InChI=1S/C24H34O5/c1-14(26)24(29-15(2)27)10-7-20-18-11-16(13-25)21-12-17(28)5-8-22(21,3)19(18)6-9-23(20,24)4/h12,16,18-20,25H,5-11,13H2,1-4H3/t16?,18-,19+,20+,22-,23+,24+/m1/s1
• InChIKey: NKGLDEZBTQRRJN-XFTPORKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-acetyl-8-(hydroxymethyl)-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: (1S,2R,10R,11S,14R,15S)-14-acetyl-8-(hydroxymethyl)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• Synonyms: (6α/6β)-17-(Acetyloxy)-6-(hydroxymethyl)pregn-4-ene-3,20-dione; Megestrol Acetate Impurity; 6(α/β)-Hydroxymethyl Megestrol Acetate (Megestrol Acetate Impurity)(Mixture of Diastereomers)

Database IDs

• PubChem SID: 164227002
• PubChem CID: 71749255

CALCULATED PROPERTIES

• Acid pKa: 17.586067
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.770599
• LogD (pH = 7.4): 2.770599
• Log P: 2.770599
• Molar Refractivity: 109.6571 cm^3
• Polarizability: 43.32088 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H950785

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)