berberine   Click here for help

GtoPdb Ligand ID: 11353

Synonyms: umbellatine
PDB Ligand
Comment: Berberine is a botanical alkaloid compound that has found use in traditional medicine in some countries. It is poorly orally bioavailable and interacts adversely with prescription drugs.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 0
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 40.8
Molecular weight 336.12
XLogP 4.7
No. Lipinski's rules broken 0
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Canonical SMILES COc1c(OC)ccc2c1c[n+]1CCc3c(c1c2)cc1c(c3)OCO1
Isomeric SMILES COc1c(OC)ccc2c1c[n+]1CCc3c(c1c2)cc1c(c3)OCO1
InChI InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CYP2D6 Hs Inhibitor Inhibition 5.4 pIC50 - 1
pIC50 5.4 [1]