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

• ChemBase ID: 129962
• Molecular Formular: C20H20O9
• Molecular Mass: 404.3674
• Monoisotopic Mass: 404.11073222
• SMILES: O=C(O)[C@H]1O[C@@H](Oc2cc(O)cc(/C=C/c3ccc(O)cc3)c2)[C@H](O)[C@@H](O)[C@@H]1O
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](Oc2cc(/C=C/c3ccc(cc3)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
• InChIKey: QWSAYEBSTMCFKY-OTPOQTMVSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 387372-17-0
• PubChem SID: 162224248
• PubChem CID: 5273285
• Chemspider ID: 4437760
• Wikipedia Title: Trans-Resveratrol-3-O-glucuronide

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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: >150°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Safety Statements: R

DETAILS

Toronto Research Chemicals - R150015

A 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