(2R,3R,4R,5S,6R)-6-{4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl](1,2,3,4,5,6-13C6)phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 177416
• Molecular Formular: C20H20O9
• Molecular Mass: 410.32332903
• Monoisotopic Mass: 410.13086125
• SMILES: O1[C@@H]([C@@H]([C@@H]([C@H]([C@H]1C(=O)O)O)O)O)O[13c]1[13cH][13cH][13c](/C=C/c2cc(cc(O)c2)O)[13cH][13cH]1
• Canonical SMILES: Oc1cc(/C=C/[13c]2[13cH][13cH][13c]([13cH][13cH]2)O[C@H]2O[C@H](C(=O)O)[C@@H]([C@H]([C@H]2O)O)O)cc(c1)O
• InChI: InChI=1S/C20H20O9/c21-12-7-11(8-13(22)9-12)2-1-10-3-5-14(6-4-10)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+/m1/s1/i3+1,4+1,5+1,6+1,10+1,14+1
• InChIKey: CDEBVTGYVFHDMA-DNIMFHOTSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 164233326
• PubChem CID: 71752005

CALCULATED PROPERTIES

• Acid pKa: 3.2601843
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -0.76606804
• LogD (pH = 7.4): -1.9871286
• Log P: 1.4545974
• Molar Refractivity: 99.4673 cm^3
• Polarizability: 38.917168 Å^3
• Polar Surface Area: 156.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R150027

A labelled metabolite of trans Resveratrol (150000).

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