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

• ChemBase ID: 168844
• Molecular Formular: C24H21F2NO3
• Molecular Mass: 409.4252464
• Monoisotopic Mass: 409.14894998
• SMILES: c1cc(ccc1[C@H](CC[C@@H]1C(=O)N([C@@H]1c1ccc(cc1)O)c1ccc(cc1)F)O)F
• Canonical SMILES: Oc1ccc(cc1)[C@@H]1[C@H](CC[C@@H](c2ccc(cc2)F)O)C(=O)N1c1ccc(cc1)F
• InChI: InChI=1S/C24H21F2NO3/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/h1-12,21-23,28-29H,13-14H2/t21-,22-,23+/m0/s1
• InChIKey: OLNTVTPDXPETLC-RJGXRXQPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
• IUPAC Traditional name: (3S,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
• Synonyms: (3S,4S)-rel-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone; rac-(3S,4S,3'S)-Ezetimibe

Database IDs

• PubChem SID: 162262976
• PubChem CID: 42066912

CALCULATED PROPERTIES

• Acid pKa: 9.484299
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.559083
• LogD (pH = 7.4): 4.555587
• Log P: 4.559128
• Molar Refractivity: 108.8617 cm^3
• Polarizability: 41.585533 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E975015

The racemic analogue of the 3-epimer impurity of Ezetimibe (E975000), a cholesterol absorption inhibitor.

REFERENCES

• van Heek, M., at al.: J. Pharmacol. Exp. Ther., 283, 157 (1997)
• van Heek, M., at al.: Brit. J. Pharmacol., 129, 1748 (2000)