(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-[4-hydroxy(1,2,3,4,5,6-13C6)phenyl]ethenyl]phenoxy}oxane-2-carboxylic acid

• ChemBase ID: 177413
• Molecular Formular: C20H20O9
• Molecular Mass: 410.32332903
• Monoisotopic Mass: 410.13086125
• SMILES: O([C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)c1cc(cc(c1)/C=C/[13c]1[13cH][13cH][13c]([13cH][13cH]1)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2cc(/C=C/[13c]3[13cH][13cH][13c]([13cH][13cH]3)O)cc(c2)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C20H20O9/c21-12-5-3-10(4-6-12)1-2-11-7-13(22)9-14(8-11)28-20-17(25)15(23)16(24)18(29-20)19(26)27/h1-9,15-18,20-25H,(H,26,27)/b2-1+/t15-,16-,17+,18-,20+/m0/s1/i3+1,4+1,5+1,6+1,10+1,12+1
• InChIKey: QWSAYEBSTMCFKY-ONBJXNBSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-[4-hydroxy(1,2,3,4,5,6-^1^3C₆)phenyl]ethenyl]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-[4-hydroxy(1,2,3,4,5,6-^1^3C₆)phenyl]ethenyl]phenoxy}oxane-2-carboxylic acid
• Synonyms: 3-Hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl-13C6 β-D-Glucopyranosiduronic Acid; Resveratrol-13C6 3-O-Glucuronide; trans-Resveratrol-13C6 3-O-β-D-Glucuronide

Database IDs

• PubChem SID: 164233323
• PubChem CID: 71752002

CALCULATED PROPERTIES

• Acid pKa: 3.1353626
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -0.88327813
• LogD (pH = 7.4): -2.0100691
• Log P: 1.4545974
• Molar Refractivity: 99.4673 cm^3
• Polarizability: 38.91712 Å^3
• Polar Surface Area: 156.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R150017

A labelled metabolite of trans Resveratrol (R150000).

REFERENCES

• Schroder, H., et al.: Clin. Nutr., 20, 429 (2001)
• Yu, C., et al.: Pharm. Res., 19, 1907 (2001)
• Rimando, A., et al.: J. Agric. Food Chem., 52, 4713 (2001)
• Walle, T., et al.: Drug Metab. Dispos., 32, 1377 (2001)
• Ito, H., et al.: Br. J. Nutr., 94, 500 (2