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

• ChemBase ID: 164870
• Molecular Formular: C16H19ClO9
• Molecular Mass: 390.76966
• Monoisotopic Mass: 390.07175987
• 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)Cl
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)C(Oc2ccc(cc2)Cl)(C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H19ClO9/c1-16(2,26-8-5-3-7(17)4-6-8)15(23)25-14-11(20)9(18)10(19)12(24-14)13(21)22/h3-6,9-12,14,18-20H,1-2H3,(H,21,22)/t9-,10-,11+,12-,14-/m0/s1
• InChIKey: LCJVUUVMVSSIGZ-HNRZYHPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[2-(4-chlorophenoxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[2-(4-chlorophenoxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Clofibryl Glucuronide; Clofibric Acid Acyl-β-D-glucuronide (90%); 1-[2-(4-Chlorophenoxy)-2-methylpropanoate] β-D-Glucopyranuronic Acid; Clofibric β-Glucuronide; Clofibric Acid Glucuronide

Database IDs

• CAS Number: 72072-47-0
• PubChem SID: 162259004
• PubChem CID: 155696

CALCULATED PROPERTIES

• Acid pKa: 3.1442387
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.3781543
• LogD (pH = 7.4): -2.5034142
• Log P: 0.9513391
• Molar Refractivity: 84.9164 cm^3
• Polarizability: 34.731754 Å^3
• Polar Surface Area: 142.75 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 56-64°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C586940

A metabolite of Clofibric Acid.

REFERENCES

• Ding, A., et al.: Drug. Metab. Dispos., 23, 369 (1995)
• Sallustio, B., et al.: Toxicol. Appl. Pharmacol., 147, 459 (1995)
• Akira, K., et al.: Drug Metab. Dispos., 26, 457 (1995)
• Sallustio, B., et al.: Curr. Drug Metab., 1, 163 (1995)