[(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]methyl acetate

• ChemBase ID: 169764
• Molecular Formular: C24H24O11
• Molecular Mass: 488.44076
• Monoisotopic Mass: 488.13186159
• SMILES: O1[C@H]([C@@H](O)[C@H]([C@@H]([C@@H]1COC(=O)C)O)O)Oc1c(cc2c(c1)occ(c2=O)c1ccc(cc1)O)OC
• Canonical SMILES: COc1cc2c(cc1O[C@@H]1O[C@@H](COC(=O)C)[C@H]([C@@H]([C@@H]1O)O)O)occ(c2=O)c1ccc(cc1)O
• InChI: InChI=1S/C24H24O11/c1-11(25)32-10-19-21(28)22(29)23(30)24(35-19)34-18-8-16-14(7-17(18)31-2)20(27)15(9-33-16)12-3-5-13(26)6-4-12/h3-9,19,21-24,26,28-30H,10H2,1-2H3/t19-,21-,22+,23-,24-/m1/s1
• InChIKey: DUBPGEJGGVZKDD-PFKOEMKTSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 134859-96-4
• PubChem SID: 162263896
• PubChem CID: 10228095

CALCULATED PROPERTIES

• Acid pKa: 8.962558
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 0.745675
• LogD (pH = 7.4): 0.7341674
• Log P: 0.74582374
• Molar Refractivity: 117.4611 cm^3
• Polarizability: 46.583836 Å^3
• Polar Surface Area: 161.21 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G635420

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)