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

• ChemBase ID: 169763
• Molecular Formular: C22H22O10
• Molecular Mass: 446.40408
• Monoisotopic Mass: 446.1212969
• SMILES: O1[C@H]([C@@H](O)[C@H]([C@@H]([C@@H]1CO)O)O)Oc1c(cc2c(c1)occ(c2=O)c1ccc(cc1)O)OC
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2cc3occ(c(=O)c3cc2OC)c2ccc(cc2)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C22H22O10/c1-29-15-6-12-14(30-9-13(18(12)25)10-2-4-11(24)5-3-10)7-16(15)31-22-21(28)20(27)19(26)17(8-23)32-22/h2-7,9,17,19-24,26-28H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1
• InChIKey: OZBAVEKZGSOMOJ-MIUGBVLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-hydroxyphenyl)-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: glycitin
• Synonyms: 7-(β-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one; Glycitein 7-O-Glucoside; Glycitein 7-O-β-glucoside; Glycitein-7-β-O-glucoside; Glycitin

Database IDs

• CAS Number: 40246-10-4
• PubChem SID: 162263895
• PubChem CID: 187808

CALCULATED PROPERTIES

• Acid pKa: 8.962557
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 0.30454963
• LogD (pH = 7.4): 0.29304197
• Log P: 0.30469835
• Molar Refractivity: 108.3096 cm^3
• Polarizability: 42.728 Å^3
• Polar Surface Area: 155.14 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 227-230°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G635410

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