5,7-dihydroxy-2-[4-hydroxy-3-(2H3)methoxyphenyl]-4H-chromen-4-one

• ChemBase ID: 164754
• Molecular Formular: C16H12O6
• Molecular Mass: 300.26288
• Monoisotopic Mass: 300.0633881
• SMILES: c1(cc(c2c(c1)oc(cc2=O)c1cc(c(cc1)O)OC)O)O
• Canonical SMILES: COc1cc(ccc1O)c1cc(=O)c2c(o1)cc(cc2O)O
• InChI: InChI=1S/C16H12O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-7,17-19H,1H3
• InChIKey: SCZVLDHREVKTSH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-[4-hydroxy-3-(^2H₃)methoxyphenyl]-4H-chromen-4-one
• IUPAC Traditional name: 5,7-dihydroxy-2-[4-hydroxy-3-(^2H₃)methoxyphenyl]chromen-4-one
• Synonyms: 5,7-Dihydroxy-2-[4-hydroxy-3-(methoxy-d3)phenyl]-4H-1-benzopyran-4-one; 4',5,7-Trihydroxy-3'-(methoxy-d3)flavone; 3'-(Methoxy-d3)-4',5,7-trihydroxyflavone; 3'-(Methoxy-d3)apigenin; 3'-O-(Methyl-d3)luteolin; 5,7,4'-Trihydroxy-3'-(methoxy-d3)flavone; Chrysoriol-d3; Luteolin 3'-Methyl Ether-d3; Chrysoeriol-d3

Database IDs

• PubChem SID: 162258889
• PubChem CID: 71314865

CALCULATED PROPERTIES

• Acid pKa: 6.6366467
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.5186331
• LogD (pH = 7.4): 1.7240281
• Log P: 2.549018
• Molar Refractivity: 79.3771 cm^3
• Polarizability: 29.651958 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C432822

The labelled analogue of a methoxyflavonoid that selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells. A metabolite of Luteolin (L475000).

REFERENCES

• Takemura, H. et al.: J. Steroid Biochem. Mol. Biol., 118, 70 (2010)
• Petroianu, G. et al.: Open Med. Chem. J., 3, 1 (2010)
• Takemura, H. et al.: Toxicology, 274, 42 (2010)