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
1. Coombs TC, Tanega C, Shen M, Wang JL, Auld DS, Gerritz SW, Schoenen FJ, Thomas CJ, Aubé J. (2013)
Small-molecule pyrimidine inhibitors of the cdc2-like (Clk) and dual specificity tyrosine phosphorylation-regulated (Dyrk) kinases: development of chemical probe ML315.
Bioorg Med Chem Lett, 23 (12): 3654-61. [PMID:23642479]
2. Ferraz CAA, de Oliveira Júnior RG, Picot L, da Silva Almeida JRG, Nunes XP. (2019)
Pre-clinical investigations of β-carboline alkaloids as antidepressant agents: A systematic review.
Fitoterapia, 137: 104196. [PMID:31175948]
3. Göckler N, Jofre G, Papadopoulos C, Soppa U, Tejedor FJ, Becker W. (2009)
Harmine specifically inhibits protein kinase DYRK1A and interferes with neurite formation.
FEBS J, 276 (21): 6324-37. [PMID:19796173]
4. Herraiz T, Guillén H. (2018)
Monoamine Oxidase-A Inhibition and Associated Antioxidant Activity in Plant Extracts with Potential Antidepressant Actions.
Biomed Res Int, 2018: 4810394. [PMID:29568754]
5. Jiang B, Meng L, Zou N, Wang H, Li S, Huang L, Cheng X, Wang Z, Chen W, Wang C. (2019)
Mechanism-based pharmacokinetics-pharmacodynamics studies of harmine and harmaline on neurotransmitters regulatory effects in healthy rats: Challenge on monoamine oxidase and acetylcholinesterase inhibition.
Phytomedicine, 62: 152967. [PMID:31154274]
6. Liu X, Li M, Tan S, Wang C, Fan S, Huang C. (2017)
Harmine is an inflammatory inhibitor through the suppression of NF-κB signaling.
Biochem Biophys Res Commun, 489 (3): 332-338. [PMID:28551404]
7. Miralles A, Esteban S, Sastre-Coll A, Moranta D, Asensio VJ, García-Sevilla JA. (2005)
High-affinity binding of beta-carbolines to imidazoline I2B receptors and MAO-A in rat tissues: norharman blocks the effect of morphine withdrawal on DOPA/noradrenaline synthesis in the brain.
Eur J Pharmacol, 518 (2-3): 234-42. [PMID:16061219]