methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[(2S,3R)-3-[(3R)-3-(acetyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}oxane-2-carboxylate

• ChemBase ID: 159258
• Molecular Formular: C39H39F2NO13
• Molecular Mass: 767.7226664
• Monoisotopic Mass: 767.23894675
• SMILES: c1cc(ccc1[C@@H](CC[C@H]1C(=O)N([C@@H]1c1ccc(cc1)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)c1ccc(cc1)F)OC(=O)C)F
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)[C@@H]2[C@@H](CC[C@H](c3ccc(cc3)F)OC(=O)C)C(=O)N2c2ccc(cc2)F)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C39H39F2NO13/c1-20(43)50-31(24-6-10-26(40)11-7-24)19-18-30-32(42(37(30)47)28-14-12-27(41)13-15-28)25-8-16-29(17-9-25)54-39-36(53-23(4)46)34(52-22(3)45)33(51-21(2)44)35(55-39)38(48)49-5/h6-17,30-36,39H,18-19H2,1-5H3/t30-,31-,32-,33+,34+,35+,36-,39-/m1/s1
• InChIKey: NZXOBPVQKQLFNG-DDDXWAHESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[(2S,3R)-3-[(3R)-3-(acetyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{4-[(2S,3R)-3-[(3R)-3-(acetyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}oxane-2-carboxylate
• Synonyms: 4-[(2S,3R)-3-[(3S)-3-(Acetyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxo-2-azetidinyl]phenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate; 3-O-Acetyl Ezetimibe 2,3,4-Tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• CAS Number: 190448-56-7
• PubChem SID: 162253393
• PubChem CID: 71312881

CALCULATED PROPERTIES

• Acid pKa: 18.597858
• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 4.52173
• LogD (pH = 7.4): 4.52173
• Log P: 4.52173
• Molar Refractivity: 182.2486 cm^3
• Polarizability: 72.753204 Å^3
• Polar Surface Area: 170.27 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloroform,
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A173800

Intermediate in the preparation of Phase-II metabolites of Ezetimibe. Glucuronide azetidinone cholesterol absorption inhibitor.

REFERENCES

• Mutlib, A., et al.: Drug Metab. Dispos., 20, 451 (1992)
• Clader, J., et al.: J. Med. Chem., 39, 3684 (1992)
• van Heek, M., et al.: J. Pharmacol. Exp. Ther., 283, 157 (1992)