melatonin   Click here for help

GtoPdb Ligand ID: 224

Abbreviated name: MLT
Synonyms: Circadin®
Approved drug PDB Ligand Immunopharmacology Ligand
melatonin is an approved drug (EMA (2007))
Compound class: Metabolite or derivative
Comment: Melatonin is a hormone involved in regulating circadian rhythms in animals. Melatonin activates a family of melatonin receptors.

SARS-CoV-2 and COVID-19: The effect of viral infection (including by influenza and SARS-CoV-2) on the melatonergic pathway, and how this might modulate the inflammatory response was reviewed by Anderson and Reiter in May 2020 [1].
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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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View more information in the IUPHAR Pharmacology Education Project: melatonin

melatonin is commercially available from our sponsors

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 CDK toolkit. 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 2
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 54.12
Molecular weight 232.12
XLogP 1.6
No. Lipinski's rules broken 0
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.

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Canonical SMILES COc1ccc2c(c1)c(CCNC(=O)C)c[nH]2
Isomeric SMILES COc1ccc2c(c1)c(CCNC(=O)C)c[nH]2
InChI InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
InChI Key DRLFMBDRBRZALE-UHFFFAOYSA-N
References
1. Anderson G, Reiter RJ. (2020)
Melatonin: Roles in influenza, Covid-19, and other viral infections.
Rev Med Virol, 30 (3): e2109. DOI: 10.1002/rmv.2109 [PMID:32314850]
2. Audinot V, Mailliet F, Lahaye-Brasseur C, Bonnaud A, Le Gall A, Amossé C, Dromaint S, Rodriguez M, Nagel N, Galizzi JP et al.. (2003)
New selective ligands of human cloned melatonin MT1 and MT2 receptors.
Naunyn Schmiedebergs Arch Pharmacol, 367 (6): 553-61. [PMID:12764576]
3. Calvo JR, González-Yanes C, Maldonado MD. (2013)
The role of melatonin in the cells of the innate immunity: a review.
J Pineal Res, 55 (2): 103-20. [PMID:23889107]
4. Carlberg C. (2000)
Gene regulation by melatonin.
Ann N Y Acad Sci, 917: 387-96. [PMID:11268365]
5. Carrillo-Vico A, Lardone PJ, Alvarez-Sánchez N, Rodríguez-Rodríguez A, Guerrero JM. (2013)
Melatonin: buffering the immune system.
Int J Mol Sci, 14 (4): 8638-83. [PMID:23609496]
6. Dubocovich ML. (1985)
Characterization of a retinal melatonin receptor.
J Pharmacol Exp Ther, 234 (2): 395-401. [PMID:2991499]
7. Dubocovich ML, Masana MI, Iacob S, Sauri DM. (1997)
Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor.
Naunyn Schmiedebergs Arch Pharmacol, 355 (3): 365-75. [PMID:9089668]
8. Huang SH, Cao XJ, Wei W. (2008)
Melatonin decreases TLR3-mediated inflammatory factor expression via inhibition of NF-kappa B activation in respiratory syncytial virus-infected RAW264.7 macrophages.
J Pineal Res, 45 (1): 93-100. [PMID:18312297]
9. Jahanban-Esfahlan R, Mehrzadi S, Reiter RJ, Seidi K, Majidinia M, Baghi HB, Khatami N, Yousefi B, Sadeghpour A. (2018)
Melatonin in regulation of inflammatory pathways in rheumatoid arthritis and osteoarthritis: involvement of circadian clock genes.
Br J Pharmacol, 175 (16): 3230-3238. [PMID:28585236]
10. Millan MJ, Gobert A, Lejeune F, Dekeyne A, Newman-Tancredi A, Pasteau V, Rivet JM, Cussac D. (2003)
The novel melatonin agonist agomelatine (S20098) is an antagonist at 5-hydroxytryptamine2C receptors, blockade of which enhances the activity of frontocortical dopaminergic and adrenergic pathways.
J Pharmacol Exp Ther, 306 (3): 954-64. [PMID:12750432]
11. Steinhilber D, Brungs M, Werz O, Wiesenberg I, Danielsson C, Kahlen JP, Nayeri S, Schräder M, Carlberg C. (1995)
The nuclear receptor for melatonin represses 5-lipoxygenase gene expression in human B lymphocytes.
J Biol Chem, 270 (13): 7037-40. [PMID:7706239]
12. Xia MZ, Liang YL, Wang H, Chen X, Huang YY, Zhang ZH, Chen YH, Zhang C, Zhao M, Xu DX et al.. (2012)
Melatonin modulates TLR4-mediated inflammatory genes through MyD88- and TRIF-dependent signaling pathways in lipopolysaccharide-stimulated RAW264.7 cells.
J Pineal Res, 53 (4): 325-34. [PMID:22537289]
13. Xu X, Wang G, Ai L, Shi J, Zhang J, Chen YX. (2018)
Melatonin suppresses TLR9-triggered proinflammatory cytokine production in macrophages by inhibiting ERK1/2 and AKT activation.
Sci Rep, 8 (1): 15579. [PMID:30349079]