(1R)-3-[(2S,3R)-2-[4-(acetyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl acetate

• ChemBase ID: 168845
• Molecular Formular: C28H25F2NO5
• Molecular Mass: 493.4986064
• Monoisotopic Mass: 493.17007935
• SMILES: c1cc(ccc1[C@@H](CC[C@H]1C(=O)N([C@@H]1c1ccc(cc1)OC(=O)C)c1ccc(cc1)F)OC(=O)C)F
• Canonical SMILES: CC(=O)O[C@@H](c1ccc(cc1)F)CC[C@H]1C(=O)N([C@@H]1c1ccc(cc1)OC(=O)C)c1ccc(cc1)F
• InChI: InChI=1S/C28H25F2NO5/c1-17(32)35-24-13-5-20(6-14-24)27-25(28(34)31(27)23-11-9-22(30)10-12-23)15-16-26(36-18(2)33)19-3-7-21(29)8-4-19/h3-14,25-27H,15-16H2,1-2H3/t25-,26-,27-/m1/s1
• InChIKey: DCEGDCNFJOXKQY-ZONZVBGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-3-[(2S,3R)-2-[4-(acetyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl acetate
• IUPAC Traditional name: (1R)-3-[(2S,3R)-2-[4-(acetyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl acetate
• Synonyms: (3R,4S)-3-[(3S)-3-(Acetyloxy)-3-(4-fluorophenyl)propyl]-4-[4-(acetyloxy)phenyl]-1-(4-fluorophenyl)-2-azetidinone; Ezetimibe Diacetate

Database IDs

• CAS Number: 163380-20-9
• PubChem SID: 162262977
• PubChem CID: 10505317

CALCULATED PROPERTIES

• Acid pKa: 18.597858
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.9110794
• LogD (pH = 7.4): 4.9110794
• Log P: 4.9110794
• Molar Refractivity: 127.1647 cm^3
• Polarizability: 49.275497 Å^3
• Polar Surface Area: 72.91 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Foam

DETAILS

Toronto Research Chemicals - E975020

Protected Ezetimibe derivative.

REFERENCES

• Rosenblum, S., et al.: J. Med. Chem., 41, 973 (1998)