(2R,3R,4R,5S,6R)-6-[(2-{4-[(4-chlorophenyl)(hydroxy)methyl]phenoxy}-2-methylpropanoyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168893
• Molecular Formular: C23H25ClO10
• Molecular Mass: 496.8916
• Monoisotopic Mass: 496.11362468
• SMILES: c1c(ccc(c1)OC(C(=O)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)(C)C)C(c1ccc(cc1)Cl)O
• Canonical SMILES: OC(=O)[C@H]1O[C@H](OC(=O)C(Oc2ccc(cc2)C(c2ccc(cc2)Cl)O)(C)C)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C23H25ClO10/c1-23(2,22(31)33-21-18(28)16(26)17(27)19(32-21)20(29)30)34-14-9-5-12(6-10-14)15(25)11-3-7-13(24)8-4-11/h3-10,15-19,21,25-28H,1-2H3,(H,29,30)/t15?,16-,17-,18+,19-,21-/m1/s1
• InChIKey: UJNGWDHZBYRDRO-ZFDAFNFFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-[(2-{4-[(4-chlorophenyl)(hydroxy)methyl]phenoxy}-2-methylpropanoyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-[(2-{4-[(4-chlorophenyl)(hydroxy)methyl]phenoxy}-2-methylpropanoyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[2-[4-[(4-Chlorophenyl)hydroxymethyl]phenoxy]-2-methylpropanoate] β-D-Glucopyranuronic Acid; Fenirofibrate Acyl-β-D-glucuronide (Mixture of Diastereomers)

Database IDs

• CAS Number: 168844-25-5
• PubChem SID: 162263025
• PubChem CID: 71316722

CALCULATED PROPERTIES

• Acid pKa: 3.1615925
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.34505787
• LogD (pH = 7.4): -1.4837346
• Log P: 1.9682295
• Molar Refractivity: 116.0151 cm^3
• Polarizability: 46.668964 Å^3
• Polar Surface Area: 162.98 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F247710

A metabolite of Fenofibrate (F248640).

REFERENCES

• Robertson, D., et al.: Toxicol. Sci., 85, 809 (2005)
• Chen, C., et al.: Chem. Res. Toxicol., 20, 531 (2005)
• Chen, C., et al.: J. Biol. Chem., 283, 4543 (2005)
• Zhu, M., et al.: Drug Metab. Dispos., 34, 1722 (2005)