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

• ChemBase ID: 169765
• Molecular Formular: C25H24O13
• Molecular Mass: 532.45026
• Monoisotopic Mass: 532.12169083
• SMILES: O1[C@H]([C@@H](O)[C@H]([C@@H]([C@@H]1COC(=O)CC(=O)O)O)O)Oc1c(cc2c(c1)occ(c2=O)c1ccc(cc1)O)OC
• Canonical SMILES: COc1cc2c(cc1O[C@@H]1O[C@@H](COC(=O)CC(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)occ(c2=O)c1ccc(cc1)O
• InChI: InChI=1S/C25H24O13/c1-34-16-6-13-15(35-9-14(21(13)30)11-2-4-12(26)5-3-11)7-17(16)37-25-24(33)23(32)22(31)18(38-25)10-36-20(29)8-19(27)28/h2-7,9,18,22-26,31-33H,8,10H2,1H3,(H,27,28)/t18-,22-,23+,24-,25-/m1/s1
• InChIKey: OWMHCYFEIJPHFB-GOZZSVHWSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 137705-39-6
• PubChem SID: 162263897
• PubChem CID: 23724657

CALCULATED PROPERTIES

• Acid pKa: 3.3502285
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -1.4971828
• LogD (pH = 7.4): -2.7885714
• Log P: 0.6380522
• Molar Refractivity: 123.8052 cm^3
• Polarizability: 49.065884 Å^3
• Polar Surface Area: 198.51 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G635425

A metabolite of isoflavone derivatives. A derivative of Glycitein (G635410). 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)