Ligand id: 224

Name: melatonin

Abbreviated name: MLT

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Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

1. Audinot V, Mailliet F, Lahaye-Brasseur C, Bonnaud A, Le Gall A, Amossé C, Dromaint S, Rodriguez M, Nagel N, Galizzi JP, Malpaux B, Guillaumet G, Lesieur D, Lefoulon F, Renard P, Delagrange P, Boutin JA. (2003)
New selective ligands of human cloned melatonin MT1 and MT2 receptors.
Naunyn Schmiedebergs Arch Pharmacol, 367: 553-561. [PMID:12764576]
2. 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]
3. Carlberg C. (2000)
Gene regulation by melatonin.
Ann. N. Y. Acad. Sci., 917: 387-96. [PMID:11268365]
4. 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]
5. Dubocovich ML. (1985)
Characterization of a retinal melatonin receptor.
J. Pharmacol. Exp. Ther., 234 (2): 395-401. [PMID:2991499]
6. Dubocovich ML, Masana MI, Iacob S, Sauri DM. (1997)
Melatonin receptor antagonists that differentiate between the human Mel1aand Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor.
Naunyn Schmiedebergs Arch. Pharmacol., 355: 365-375. [PMID:9089668]
7. 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]
8. 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]
9. 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: 954-964. [PMID:12750432]
10. 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]
11. 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]
12. 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]