[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
Click here for help

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.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

✖
Click here for structure editor
SMILES / InChI / InChIKey
Click here for help

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.

✖
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
Classification Click here for help
Compound class Endogenous peptide in human, mouse or rat
Ligand families/groups Neuropeptides
IUPAC Name Click here for help
(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
International Nonproprietary Names Click here for help
INN number INN
8875 metenkefalin
Synonyms Click here for help
1-5 Adrenorphin | [Met]-enkephalin | IRT-101 | methionine enkephalin | np2 enkephalin | opioid growth factor (OGF)
Gene/Precursor Click here for help
Gene symbol Gene name Species Precursor protein name Synonyms
PENK proenkephalin Human proenkephalin-A preproenkephalin
Penk preproenkephalin Mouse proenkephalin-A ENK, Penk, Penk1, PPA
Penk proenkephalin Rat proenkephalin-A Enk, enkephalin, MGC93514, Penk1, Penk2, Penk-rs, preproenkephalin 2, preproenkephalin, related sequence, proenkephalin, proenkephalin 1, proenkephalin 2, proenkephalin-A, proenkephalin related sequence, proenkephalin, related sequence
Database Links Click here for help
Specialist databases
GPCRdb Ligand [Met]enkephalin
Other databases
BindingDB Ligand 50019056
CAS Registry No. 58569-55-4
ChEMBL Ligand CHEMBL13786
Ensembl Gene ENSRNOG00000008943 (Rn), ENSMUSG00000045573 (Mm), ENSG00000181195 (Hs)
GtoPdb PubChem SID 135651808
Human Protein Atlas ENSG00000181195 (Hs)
PubChem CID 443363
Search Google for chemical match using the InChIKey YFGBQHOOROIVKG-FKBYEOEOSA-N
Search Google for chemicals with the same backbone YFGBQHOOROIVKG
Search PubMed clinical trials metenkefalin
Search PubMed titles metenkefalin
Search PubMed titles/abstracts metenkefalin
UniChem Compound Search for chemical match using the InChIKey YFGBQHOOROIVKG-FKBYEOEOSA-N
UniChem Connectivity Search for chemical match using the InChIKey YFGBQHOOROIVKG-FKBYEOEOSA-N
UniProtKB P04094 (Rn), P22005 (Mm), P01210 (Hs)
Wikipedia Metenkefalin