harmine   Click here for help

GtoPdb Ligand ID: 9352

PDB Ligand Immunopharmacology Ligand
Compound class: Natural product
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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
InChI Key BXNJHAXVSOCGBA-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
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]