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

• ChemBase ID: 169613
• Molecular Formular: C24H22O13
• Molecular Mass: 518.42368
• Monoisotopic Mass: 518.10604076
• SMILES: c1(cc(cc2c1c(=O)c(co2)c1ccc(cc1)O)O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)COC(=O)CC(=O)O)O
• Canonical SMILES: OC(=O)CC(=O)OC[C@@H]1O[C@@H](Oc2cc(O)c3c(c2)occ(c3=O)c2ccc(cc2)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C24H22O13/c25-11-3-1-10(2-4-11)13-8-34-15-6-12(5-14(26)19(15)20(13)30)36-24-23(33)22(32)21(31)16(37-24)9-35-18(29)7-17(27)28/h1-6,8,16,21-26,31-33H,7,9H2,(H,27,28)/t16-,21-,22+,23-,24-/m1/s1
• InChIKey: FRAUJUKWSKMNJY-RSEYPYQYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 51011-05-3
• PubChem SID: 162263745
• PubChem CID: 15934091

CALCULATED PROPERTIES

• Acid pKa: 3.3721933
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -0.97257614
• LogD (pH = 7.4): -2.3136353
• Log P: 1.1421582
• Molar Refractivity: 119.3229 cm^3
• Polarizability: 47.183857 Å^3
• Polar Surface Area: 209.51 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G350035

A metabolite of isoflavone derivatives. A derivative of Genistin (G350020). 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)