harmine   Click here for help

GtoPdb Ligand ID: 9352

PDB Ligand Immunopharmacology Ligand
Comment: Harmine is a plant-derived β-carboline alkaloid that has psychoactive activity. It has been reported as an inhibitor of dual specificity tyrosine phosphorylation regulated kinases of the Dyrk1 subfamily [1,3] and monoamine oxidase A [4-5,7]. Harmine has been tested in preclincal studies for antidepressant potential [2]
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 37.91
Molecular weight 212.09
XLogP 2.51
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc2c(c1)[nH]c1c2ccnc1C
Isomeric SMILES COc1ccc2c(c1)[nH]c1c2ccnc1C
InChI InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
dual specificity tyrosine phosphorylation regulated kinase 1A Hs Inhibitor Inhibition 7.5 pIC50 - 3
pIC50 7.5 (IC50 3.3x10-8 M) [3]
dual specificity tyrosine phosphorylation regulated kinase 1B Hs Inhibitor Inhibition 6.8 pIC50 - 3
pIC50 6.8 (IC50 1.66x10-7 M) [3]