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

• ChemBase ID: 169612
• Molecular Formular: C21H20O10
• Molecular Mass: 432.3775
• Monoisotopic Mass: 432.10564684
• SMILES: Oc1ccc(cc1)c1coc2c(c(cc(c2)O[C@@H]2O[C@H]([C@H](O)[C@H]([C@H]2O)O)CO)O)c1=O
• Canonical SMILES: 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/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2/t15-,18-,19+,20+,21+/m0/s1
• InChIKey: ZCOLJUOHXJRHDI-NWRWZVFGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: 5-hydroxy-3-(4-hydroxyphenyl)-7-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
• Synonyms: Genistein 7-O-Glucoside; Genistein-7-β-O-Glucopyranoside; 7-(β-D-Glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Genistoside; NSC 5112; Genistin

Database IDs

• CAS Number: 529-59-9
• PubChem SID: 162263744
• PubChem CID: 71317062

CALCULATED PROPERTIES

• Acid pKa: 8.356791
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): 0.80820525
• LogD (pH = 7.4): 0.7627874
• Log P: 0.8088043
• Molar Refractivity: 103.8273 cm^3
• Polarizability: 40.83827 Å^3
• Polar Surface Area: 166.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White to Grey Solid
• Melting Point: 274-276°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - G350020

A derivative of Genistein. 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)