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

• ChemBase ID: 177414
• Molecular Formular: C20H20O9
• Molecular Mass: 404.3674
• Monoisotopic Mass: 404.11073222
• SMILES: Oc1cc(cc(c1)/C=C\c1ccc(cc1)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)O
• Canonical SMILES: Oc1cc(/C=C\c2ccc(cc2)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+/m0/s1
• InChIKey: CDEBVTGYVFHDMA-BMPGWQKJSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 387372-26-1
• PubChem SID: 164233324
• PubChem CID: 71752003

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

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Light Brown Solid
• Melting Point: >100°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -86°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R150020

A metabolite of cis Resveratrol.

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