[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
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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2D Structure
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SMILES / InChI / InChIKey
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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
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
BindingDB Ligand 50019056
CAS Registry No. 58569-55-4
ChEMBL Ligand CHEMBL13786
Ensembl Gene ENSG00000181195 (Hs), ENSRNOG00000008943 (Rn), ENSMUSG00000045573 (Mm)
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
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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