methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(Z)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxane-2-carboxylate

• ChemBase ID: 177424
• Molecular Formular: C21H22O9
• Molecular Mass: 418.39398
• Monoisotopic Mass: 418.12638228
• SMILES: O([C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)OC)O)O)O)c1cc(cc(c1)/C=C\c1ccc(cc1)O)O
• Canonical SMILES: COC(=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/C21H22O9/c1-28-20(27)19-17(25)16(24)18(26)21(30-19)29-15-9-12(8-14(23)10-15)3-2-11-4-6-13(22)7-5-11/h2-10,16-19,21-26H,1H3/b3-2-/t16-,17-,18+,19-,21+/m0/s1
• InChIKey: MZBXGSXFXCHWLG-DLEPXKDTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(Z)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(Z)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxane-2-carboxylate
• Synonyms: 3-Hydroxy-5-[(1Z)-2-(4-hydroxyphenyl)ethenyl]phenyl β-D-Glucopyranosiduronic Acid Methyl Ester; cis Resveratrol 3-O-β-D-Glucuronide Methyl Ester

Database IDs

• PubChem SID: 164233334
• PubChem CID: 71752011

CALCULATED PROPERTIES

• Acid pKa: 9.101935
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 1.6003834
• LogD (pH = 7.4): 1.591961
• Log P: 1.6004914
• Molar Refractivity: 104.2364 cm^3
• Polarizability: 40.98463 Å^3
• Polar Surface Area: 145.91 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R150060

Intermediate in the preparation of cis Resveratrol metabolite.