(2S,3S,4S,5R,6R)-6-[(1S)-3-[(2S,3R)-1-[4-fluoro(2H4)phenyl]-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168850
• Molecular Formular: C30H29F2NO9
• Molecular Mass: 585.5493664
• Monoisotopic Mass: 585.18103795
• SMILES: C1(=O)[C@@H]([C@H](N1c1ccc(cc1)F)c1ccc(cc1)O)CC[C@@H](c1ccc(cc1)F)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: Oc1ccc(cc1)[C@@H]1[C@@H](CC[C@@H](c2ccc(cc2)F)O[C@@H]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)C(=O)N1c1ccc(cc1)F
• InChI: InChI=1S/C30H29F2NO9/c31-17-5-1-15(2-6-17)22(41-30-26(37)24(35)25(36)27(42-30)29(39)40)14-13-21-23(16-3-11-20(34)12-4-16)33(28(21)38)19-9-7-18(32)8-10-19/h1-12,21-27,30,34-37H,13-14H2,(H,39,40)/t21-,22+,23-,24+,25+,26-,27+,30-/m1/s1
• InChIKey: MPXLJVWGRVISEQ-ADEYADIWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(1S)-3-[(2S,3R)-1-[4-fluoro(^2H₄)phenyl]-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(1S)-3-[(2S,3R)-1-[4-fluoro(^2H₄)phenyl]-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (1S)-1-(4-Fluorophenyl)-3-[(2S,3R)-1-(4-fluorophenyl-d4)-2-(4-hydroxyphenyl)-4-oxo-3-azetidinyl]propyl β-D-Glucopyranosiduronic Acid; SCH 488128-d4; Ezetimibe Hydroxy-d4 β-D-Glucuronide

Database IDs

• PubChem SID: 162262982
• PubChem CID: 71316705

CALCULATED PROPERTIES

• Acid pKa: 3.3605328
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 0.9832578
• LogD (pH = 7.4): -0.3075385
• Log P: 3.1085668
• Molar Refractivity: 141.1424 cm^3
• Polarizability: 55.29539 Å^3
• Polar Surface Area: 156.99 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E975037

A labelled metabolite of Ezetimibe. Antilipemic.

REFERENCES

• Shah, V., et al.: J. Pharm. Sci., 17, 1551 (2000)
• Van Heek, M., et al.: Br. J. Pharmacol., 134, 409 (2000)
• Patrick, J., et al.: Drug Metab. Dispos., 30, 430 (2000)