(2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-(2H3)methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168943
• Molecular Formular: C16H18O10
• Molecular Mass: 370.30812
• Monoisotopic Mass: 370.08999678
• SMILES: c1c(c(cc(c1)/C=C/C(=O)O)OC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: COc1cc(/C=C/C(=O)O)ccc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C16H18O10/c1-24-9-6-7(3-5-10(17)18)2-4-8(9)25-16-13(21)11(19)12(20)14(26-16)15(22)23/h2-6,11-14,16,19-21H,1H3,(H,17,18)(H,22,23)/b5-3+/t11-,12-,13+,14-,16+/m0/s1
• InChIKey: TWSIWBHKRJLZCF-MBAOVNHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-(^2H₃)methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-(^2H₃)methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-(2-Carboxyethenyl)-2-(methoxy-d3)phenyl β-D-Glucopyranosiduronic Acid; Ferulic Acid-d3 4-O-β-D-Glucuronide

Database IDs

• PubChem SID: 162263075
• PubChem CID: 71316748

CALCULATED PROPERTIES

• Acid pKa: 3.0077899
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.5222306
• LogD (pH = 7.4): -7.0796423
• Log P: -0.27294388
• Molar Refractivity: 83.5158 cm^3
• Polarizability: 33.102245 Å^3
• Polar Surface Area: 162.98 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F308912

Labelled Ferulic Acid 4-O-β-D-Glucuronide, a metabolite of Ferulic Acid (F308910) and Caffeic Acid (C080000). Ferulic Acid 4-O-β-D-Glucuronide is one of the circulating metabolites in human plasma after coffee consumption.

REFERENCES

• Su, M. et al.: Zhong. Zian. Ying. Yao., 26, 501 (2009)
• Rondini, L. et al.: J. Agric. Food Chem., 52, 4338 (2009)
• Redeuil, K. et al.: J. Chrom. A, 1218, 4678 (2009)