[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl acetate

• ChemBase ID: 165362
• Molecular Formular: C23H22O10
• Molecular Mass: 458.41478
• Monoisotopic Mass: 458.1212969
• SMILES: O1[C@H]([C@@H](O)[C@H]([C@@H]([C@@H]1COC(=O)C)O)O)Oc1ccc2c(c1)occ(c2=O)c1ccc(cc1)O
• Canonical SMILES: CC(=O)OC[C@@H]1O[C@@H](Oc2ccc3c(c2)occ(c3=O)c2ccc(cc2)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H22O10/c1-11(24)30-10-18-20(27)21(28)22(29)23(33-18)32-14-6-7-15-17(8-14)31-9-16(19(15)26)12-2-4-13(25)5-3-12/h2-9,18,20-23,25,27-29H,10H2,1H3/t18-,20-,21+,22-,23-/m1/s1
• InChIKey: ZMOZJTDOTOZVRT-DODNOZFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl acetate
• Synonyms: 7-[(6-O-Acetyl-β-D-glucopyranosyl)oxy]-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 6''-O-Acetyldaidzin; Daidzin 6''-O-Acetate

Database IDs

• CAS Number: 71385-83-6
• PubChem SID: 162259495
• PubChem CID: 156155

CALCULATED PROPERTIES

• Acid pKa: 8.962958
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 0.9033464
• LogD (pH = 7.4): 0.8918493
• Log P: 0.903495
• Molar Refractivity: 110.9979 cm^3
• Polarizability: 44.029476 Å^3
• Polar Surface Area: 151.98 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D103540

A metabolite of isoflavone derivatives. A derivative of Daidzin (D103530). 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)