(2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 164995
• Molecular Formular: C15H16O9
• Molecular Mass: 340.28214
• Monoisotopic Mass: 340.07943209
• SMILES: c1c(ccc(c1)/C=C/C(=O)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)/C=C/c1ccc(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H16O9/c16-9(17)6-3-7-1-4-8(5-2-7)23-15-12(20)10(18)11(19)13(24-15)14(21)22/h1-6,10-13,15,18-20H,(H,16,17)(H,21,22)/b6-3+/t10-,11-,12+,13-,15+/m0/s1
• InChIKey: SOKJXEKPKWKYKR-KPGYTNHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-(2-Carboxyethenyl)phenyl β-D-Glucopyranosiduronic Acid; p-Coumaric Acid 4-O-β-D-Glucuronide

Database IDs

• CAS Number: 214689-30-2
• PubChem SID: 162259128
• PubChem CID: 71314996

CALCULATED PROPERTIES

• Acid pKa: 3.1252298
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -4.1202636
• LogD (pH = 7.4): -6.8471026
• Log P: -0.11527262
• Molar Refractivity: 77.0526 cm^3
• Polarizability: 30.537802 Å^3
• Polar Surface Area: 153.75 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C755370

p-Coumaric Acid 4-O-β-D-Glucuronide is the glucuronide conjugate of p-Coumaric Acid. p-Coumaric Acid 4-O-β-D-Glucuronide is one of the metabolites in human biological fluids after coffee consumption. p-Coumaric Acid 4-O-β-D-Glucuronide is also a metabolit

REFERENCES

• Fumeaux, R. et al.: Org. Biomol. Chem., 8, 5199 (2010)
• Zalko, D. et al.: Drug Metab. Disp., 31, 168 (2010)
• Thibaut, R. et al.: Xenobiotica, 28, 745 (2010)