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

• ChemBase ID: 165287
• Molecular Formular: C24H22O12
• Molecular Mass: 502.42428
• Monoisotopic Mass: 502.11112614
• SMILES: O1[C@H]([C@@H](O)[C@H]([C@@H]([C@@H]1COC(=O)CC(=O)O)O)O)Oc1ccc2c(c1)occ(c2=O)c1ccc(cc1)O
• Canonical SMILES: OC(=O)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/C24H22O12/c25-12-3-1-11(2-4-12)15-9-33-16-7-13(5-6-14(16)20(15)29)35-24-23(32)22(31)21(30)17(36-24)10-34-19(28)8-18(26)27/h1-7,9,17,21-25,30-32H,8,10H2,(H,26,27)/t17-,21-,22+,23-,24-/m1/s1
• InChIKey: MTXMHWSVSZKYBT-ASDZUOGYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid
• IUPAC Traditional name: malonyldaidzin
• Synonyms: 7-[[6-O-(2-Carboxyacetyl)-β-D-glucopyranosyl]oxy]-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 6''-O-Malonyldaidzin; Daidzin 6''-O-Malonate

Database IDs

• CAS Number: 124590-31-4
• PubChem SID: 162259420
• PubChem CID: 9913968

CALCULATED PROPERTIES

• Acid pKa: 3.3796062
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -1.3114866
• LogD (pH = 7.4): -2.6239026
• Log P: 0.7957235
• Molar Refractivity: 117.342 cm^3
• Polarizability: 46.506443 Å^3
• Polar Surface Area: 189.28 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D103545

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)