(2S,3S,4S,5R,6S)-6-{4-[(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168847
• Molecular Formular: C30H29F2NO9
• Molecular Mass: 585.5493664
• Monoisotopic Mass: 585.18103795
• SMILES: c1cc(ccc1[C@H](CC[C@H]1C(=O)N([C@@H]1c1ccc(cc1)O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O)c1ccc(cc1)F)O)F
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)[C@@H]2[C@@H](CC[C@@H](c3ccc(cc3)F)O)C(=O)N2c2ccc(cc2)F)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C30H29F2NO9/c31-17-5-1-15(2-6-17)22(34)14-13-21-23(33(28(21)38)19-9-7-18(32)8-10-19)16-3-11-20(12-4-16)41-30-26(37)24(35)25(36)27(42-30)29(39)40/h1-12,21-27,30,34-37H,13-14H2,(H,39,40)/t21-,22+,23-,24+,25+,26-,27+,30-/m1/s1
• InChIKey: UOFYCFMTERCNEW-ADEYADIWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{4-[(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{4-[(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-[(2S,3R)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-2-azetidinyl]phenyl β-D-Glucopyranosiduronic Acid; Ezetimibe Phenoxy Glucuronide; Sch 58235 Glucuronide; Sch 60663; EZM-G; Ezetimibe Phenoxy β-D-Glucuronide

Database IDs

• CAS Number: 190448-57-8
• PubChem SID: 162262979
• PubChem CID: 9894653

CALCULATED PROPERTIES

• Acid pKa: 3.2282856
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 0.36065388
• LogD (pH = 7.4): -0.82900447
• Log P: 2.6113343
• Molar Refractivity: 140.8735 cm^3
• Polarizability: 55.267056 Å^3
• Polar Surface Area: 156.99 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 140-150°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - E975030

Phase-II metabolite of Ezetimibe, an antihyperlipoproteinemic. A Cholesterol absorption inhibitor.This compound is very hygroscopic. Handle with care.

REFERENCES

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