(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 168148
• Molecular Formular: C21H22O9
• Molecular Mass: 418.39398
• Monoisotopic Mass: 418.12638228
• SMILES: [C@H]1(O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)Oc1ccc2c(c1)OCC(C2)c1ccc(cc1)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)OCC(C3)c2ccc(cc2)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H22O9/c22-13-4-1-10(2-5-13)12-7-11-3-6-14(8-15(11)28-9-12)29-21-18(25)16(23)17(24)19(30-21)20(26)27/h1-6,8,12,16-19,21-25H,7,9H2,(H,26,27)/t12?,16-,17-,18+,19-,21+/m0/s1
• InChIKey: XDPLKWRSVXUQBN-ATVZYYHQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid
• Synonyms: 3,4-Dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-yl-β-D-glucopyranosiduronic Acid; Equol Glucuronide; (R,S)-Equol 7-β-D-Glucuronide

Database IDs

• PubChem SID: 162262280
• PubChem CID: 71316395

CALCULATED PROPERTIES

• Acid pKa: 3.0136414
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.206253
• LogD (pH = 7.4): -2.2298293
• Log P: 1.2438843
• Molar Refractivity: 100.972 cm^3
• Polarizability: 40.06712 Å^3
• Polar Surface Area: 145.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow to Pale Orange Solid
• Melting Point: 140-142°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E593010

(R,S)-Equol 7-β-D-Glucuronide is a glucuronide metabolite of isoflavone Daidzein (D103500).

REFERENCES

• Heinonen, S., et al.: Anal. Biochem., 274, 211 (1999)
• Setchell, K., et al.: J. Nutr., 132, 3577 (1999)
• Thigpen, J., et al.: Comp. Med., 53, 607 (1999)
• Yee, S., et al.: Food Chem. Toxicol., 46, 2713 (1999)