5,7-dihydroxy-3-[4-hydroxy(2,6-2H2)phenyl]-4H-chromen-4-one

• ChemBase ID: 169609
• Molecular Formular: C15H10O5
• Molecular Mass: 270.2369
• Monoisotopic Mass: 270.05282342
• SMILES: c1c(cc2c(c1O)c(=O)c(co2)c1ccc(cc1)O)O
• Canonical SMILES: Oc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
• InChI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
• InChIKey: TZBJGXHYKVUXJN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-3-[4-hydroxy(2,6-^2H₂)phenyl]-4H-chromen-4-one
• IUPAC Traditional name: 5,7-dihydroxy-3-[4-hydroxy(2,6-^2H₂)phenyl]chromen-4-one
• Synonyms: 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one-d2; Baichanin A-d2; Bonistein-d2; 4',5,7-Trihydroxyisoflavone-d2; GeniVida-d2; Genisteol-d2; NSC 36586-d2; Prunetol-d2; Sophoricol-d2; Genistein-2',6'-d2See G350010

Database IDs

• CAS Number: 315204-48-9
• PubChem SID: 162263741
• PubChem CID: 71317061

CALCULATED PROPERTIES

• Acid pKa: 6.6064487
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.0443766
• LogD (pH = 7.4): 2.2225897
• Log P: 3.0768723
• Molar Refractivity: 71.6829 cm^3
• Polarizability: 27.11967 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; Ethyl Acetate
• Apperance: Pale Yellow Solid
• Melting Point: 304-305°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G350005

Exhibits specific inhibitory activity against tyrosine kinases,including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell prolif

REFERENCES

• Akiyama, T., et al.: J. Biol. Chem., 262, 5592 (1987)
• O'Dell, T.J., et al.: Nature, 353, 588 (1987)
• Aharonovits, O., et al.: Biochim Biophys. Acta, 1112, 181 (1987)
• Platanias, L.C., et al.: J. Biol. Chem., 267, 24053 (1987)
• Yoshida, H., et al.: Biochi