3-(4-hydroxyphenyl)-7-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

• ChemBase ID: 165360
• Molecular Formular: C21H20O9
• Molecular Mass: 416.3781
• Monoisotopic Mass: 416.11073222
• SMILES: O1[C@H]([C@H](O)C([C@@H](C1CO)O)O)Oc1ccc2c(c1)occ(c2=O)c1ccc(cc1)O
• Canonical SMILES: OCC1O[C@@H](Oc2ccc3c(c2)occ(c3=O)c2ccc(cc2)O)[C@@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16?,18-,19?,20+,21-/m1/s1
• InChIKey: KYQZWONCHDNPDP-VOUWZBHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-hydroxyphenyl)-7-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: 3-(4-hydroxyphenyl)-7-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
• Synonyms: Daidzein 7-O-Glucoside; Daidzein-7-β-O-Glucopyranoside; 7-(β-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Daidzoside; NPI 031D; Daidzin

Database IDs

• CAS Number: 552-66-9
• PubChem SID: 162259493
• PubChem CID: 71315165

CALCULATED PROPERTIES

• Acid pKa: 8.962957
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 0.46222103
• LogD (pH = 7.4): 0.45072386
• Log P: 0.46236962
• Molar Refractivity: 101.8464 cm^3
• Polarizability: 40.17439 Å^3
• Polar Surface Area: 145.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 217-222°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D103530

A metabolite of isoflavone derivatives. A derivative of Daidzin. Inhibitor.

REFERENCES

• Whalley, J.L., et al.: Bioorg. Med. Chem. Lett., 8, 1569 (1998)
• Song, T., et al.: J. Agric. Food Chem., 47, 1607 (1998)