[Met]enkephalin   Click here for help

GtoPdb Ligand ID: 1614

Synonyms: 1-5 Adrenorphin | [Met]-enkephalin | IRT-101 | methionine enkephalin | np2 enkephalin | opioid growth factor (OGF)
Immunopharmacology Ligand
Compound class: Endogenous peptide in human, mouse or rat
Comment: MET-enkephalin (MENK) is an endogenous opioid peptide. It exhibits agonist activity at the δ- and μ-opioid receptors. MENK produces immunomodulatory, neuromodulatory, antinociceptive/analgesic, antidepressant, and gastrointestinal motility modulating activities. It has cytostatic activity vs. cancer cells and may help recruit NK cells to kill tumour cells [3,5,8].
Species: Human, Mouse, Rat
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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
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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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 CSCCC(C(=O)O)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(Cc1ccc(cc1)O)N
Isomeric SMILES CSCC[C@@H](C(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N
InChI InChI=1S/C27H35N5O7S/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39)/t20-,21-,22-/m0/s1
InChI Key YFGBQHOOROIVKG-FKBYEOEOSA-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. Li X, Meng Y, Plotnikoff NP, Youkilis G, Griffin N, Wang E, Lu C, Shan F. (2015)
Methionine enkephalin (MENK) inhibits tumor growth through regulating CD4+Foxp3+ regulatory T cells (Tregs) in mice.
Cancer Biol Ther, 16 (3): 450-9. [PMID:25701137]
2. Meng F, Xie GX, Thompson RC, Mansour A, Goldstein A, Watson SJ, Akil H. (1993)
Cloning and pharmacological characterization of a rat kappa opioid receptor.
Proc Natl Acad Sci USA, 90 (21): 9954-8. [PMID:8234341]
3. Meng Y, Gao X, Chen W, Plotnikoff NP, Griffin N, Zhang G, Shan F. (2017)
Methionine enkephalin (MENK) mounts antitumor effect via regulating dendritic cells (DCs).
Int Immunopharmacol, 44: 61-71. [PMID:28088065]
4. Raynor K, Kong H, Chen Y, Yasuda K, Yu L, Bell GI, Reisine T. (1994)
Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors.
Mol Pharmacol, 45 (2): 330-4. [PMID:8114680]
5. Wang DM, Jiao X, Plotnikoff NP, Griffin N, Qi RQ, Gao XH, Shan FP. (2017)
Killing effect of methionine enkephalin on melanoma in vivo and in vitro.
Oncol Rep, 38 (4): 2132-2140. [PMID:28849104]
6. Wang Q, Gao X, Yuan Z, Wang Z, Meng Y, Cao Y, Plotnikoff NP, Griffin N, Shan F. (2014)
Methionine enkephalin (MENK) improves lymphocyte subpopulations in human peripheral blood of 50 cancer patients by inhibiting regulatory T cells (Tregs).
Hum Vaccin Immunother, 10 (7): 1836-40. [PMID:25424790]
7. Yasuda K, Raynor K, Kong H, Breder CD, Takeda J, Reisine T, Bell GI. (1993)
Cloning and functional comparison of kappa and delta opioid receptors from mouse brain.
Proc Natl Acad Sci USA, 90 (14): 6736-40. [PMID:8393575]
8. Zhao D, Plotnikoff N, Griffin N, Song T, Shan F. (2016)
Methionine enkephalin, its role in immunoregulation and cancer therapy.
Int Immunopharmacol, 37: 59-64. [PMID:26927200]