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

• ChemBase ID: 168900
• Molecular Formular: C23H23ClO10
• Molecular Mass: 494.87572
• Monoisotopic Mass: 494.09797462
• 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(=O)c1ccc(cc1)Cl
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)C(Oc2ccc(cc2)C(=O)c2ccc(cc2)Cl)(C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H23ClO10/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/h3-10,16-19,21,26-28H,1-2H3,(H,29,30)/t16-,17-,18+,19-,21-/m0/s1
• InChIKey: BHOJZVSZYFTIOZ-UNJWAJPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoate] β-D-Glucopyranuronic Acid; Fenofibric Acid Acyl-β-D-glucuronide

Database IDs

• CAS Number: 60318-63-0
• PubChem SID: 162263032
• PubChem CID: 10028724

CALCULATED PROPERTIES

• Acid pKa: 3.1243713
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 0.06269182
• LogD (pH = 7.4): -1.0471416
• Log P: 2.4106922
• Molar Refractivity: 115.4919 cm^3
• Polarizability: 46.27883 Å^3
• Polar Surface Area: 159.82 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 152-155°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F248660

A metabolite of Fenofibrate (F248640).

REFERENCES

• Heberer, T., et al.: Toxicol. Lett., 131 5 (2002)
• Larsen, T., et al.: J. Biotechnol., 113, 295 (2002)
• Escher, B., et al.: Environ. Sci. Technol., 40, 7402 (2002)