chrysin   

GtoPdb Ligand ID: 8789

Synonyms: NSC-407436
Comment: Chrysin is a dietary flavinoid. It is reported to inhibit the EROD (7-ethoxyresorufin-O-deethylase) activity of the extrahepatic cytochrome P450 enzymes CYP1A1 and CYP1B1 [1]. The compound also has antibacterial activity against Gram-negative Helicobacter pylori and is reported to inhibit H. pylori HsrA (homeostatic stress regulator) [2].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 70.67
Molecular weight 254.06
XLogP 4.07
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES Oc1cc(O)c2c(c1)oc(cc2=O)c1ccccc1
Isomeric SMILES Oc1cc(O)c2c(c1)oc(cc2=O)c1ccccc1
InChI InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H
InChI Key RTIXKCRFFJGDFG-UHFFFAOYSA-N
Bioactivity Comments
The minimum inhibitory (MIC) and minimum bactericidal (MBC) concentrations for in vitro antibacterial activity against Helicobacter pylori corresponds to the same concentration of chrysin (4-8 μg/ml) [2].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CYP1B1 Hs Inhibitor Inhibition 7.8 pKi - 1
pKi 7.8 (Ki 1.6x10-8 M) [1]
CYP1A1 Hs Inhibitor Inhibition 7.4 pKi - 1
pKi 7.4 (Ki 4.2x10-8 M) [1]