(4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)azetidin-2-one

• ChemBase ID: 168854
• Molecular Formular: C24H19F2NO3
• Molecular Mass: 407.4093664
• Monoisotopic Mass: 407.13329991
• SMILES: c1cc(ccc1C(=O)CCC1C(=O)N([C@@H]1c1ccc(cc1)O)c1ccc(cc1)F)F
• Canonical SMILES: Oc1ccc(cc1)[C@@H]1C(CCC(=O)c2ccc(cc2)F)C(=O)N1c1ccc(cc1)F
• InChI: InChI=1S/C24H19F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21,23,28H,13-14H2/t21?,23-/m1/s1
• InChIKey: UEPZDXMEEKCJSP-JFGZAKSSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)azetidin-2-one
• IUPAC Traditional name: (4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)azetidin-2-one
• Synonyms: (3R,4S)-1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)-2-azetidinone; EZM-K; Ezetimibe Ketone

Database IDs

• CAS Number: 191330-56-0
• PubChem SID: 162262986
• PubChem CID: 71316707

CALCULATED PROPERTIES

• Acid pKa: 9.484303
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.645519
• LogD (pH = 7.4): 4.6420226
• Log P: 4.6455636
• Molar Refractivity: 108.1327 cm^3
• Polarizability: 41.027866 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E975065

Phase-I metabolite of Ezetimibe (E975000).

REFERENCES

• Shah, V., et al: J. Pharm. Sci., 17, 1551 (2000)
• Van Heek, M., et al.: Br. J. Pharmacol., 134, 409 (2000)
• Watts, G., et al.: Clin. Sci.,103, 595 (2000)
• Ghosal, A., et al.: Drug Metab. Dispos., 32, 314 (2000)
• Sistla, R., et al.: J. Pharm. Biomed. Anal.