5,7-dihydroxy-3-(4-hydroxyphenyl)-8-methoxy-4H-chromen-4-one

• ChemBase ID: 105289
• Molecular Formular: C16H12O6
• Molecular Mass: 300.26288
• Monoisotopic Mass: 300.0633881
• SMILES: COc1c(O)cc(O)c2c1occ(c2=O)c1ccc(O)cc1
• Canonical SMILES: COc1c(O)cc(c2c1occ(c2=O)c1ccc(cc1)O)O
• InChI: InChI=1S/C16H12O6/c1-21-15-12(19)6-11(18)13-14(20)10(7-22-16(13)15)8-2-4-9(17)5-3-8/h2-7,17-19H,1H3
• InChIKey: UYLQOGTYNFVQQX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-3-(4-hydroxyphenyl)-8-methoxy-4H-chromen-4-one
• IUPAC Traditional name: psi-tectorigenin
• Synonyms: Isotectorigenin; Pseudotectorigenin; 5,7,4'-Trihydroxy-8-methoxyisoflavone; Psi-Tectorigenin; ψ-TECTORIGENIN

Database IDs

• CAS Number: 13111-57-4
• PubChem SID: 162092584
• PubChem CID: 5353911
• CHEMBL: 242741
• Wikipedia Title: Psi-Tectorigenin

CALCULATED PROPERTIES

• Acid pKa: 7.1244507
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.9090884
• LogD (pH = 7.4): 2.4566388
• Log P: 2.9192011
• Molar Refractivity: 78.1461 cm^3
• Polarizability: 29.653658 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 02159667

Inhibits EGF-receptor Tyrosine Kinase, which in turn blocks phosphatidylinositol turnover.

REFERENCES

• Imoto, M., et al., J. Antibiotics, 44: 915, (1991).