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))
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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2D Structure
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Physico-chemical Properties
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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
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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)
Immunopharmacology Comments
Melatonin-mediated transcriptional activation of the clock gene transcription factor RZR/ROR complex inhibits 5‐lipoxygenase [4,11] (a major producer of the proinflammatory leukotriene B4 that is found in elevated levels in synovial fluid from RA joints), and through this pathway can elicit anti‐allergic and anti‐inflammatory actions. Note: RZR/ROR refers to the retinoic acid receptor (RAR)-related orphan nuclear receptors. The interplay of melatonin and circadian clock regulation with inflammation in rheumatoid and osteoarthritis, as well as the potential protective effects of melatonin in these conditions was reviewed by Jahanban-Esfahlan et al. (2017) [9]. Accumulating evidence indicates that melatonin regulates TLR3- , TLR4- and TLR9-triggered innate immune responses in macrophages [3,5,8,12-13].