[Met]enkephalin   

GtoPdb Ligand ID: 1614

Synonyms: 1-5 Adrenorphin | [Met]-enkephalin | IRT-101 | methionine enkephalin | np2 enkephalin | opioid growth factor (OGF)
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].

HELM annotation for MENK is PEPTIDE1{Y.G.G.F.M}$$$$.
Species: Human, Mouse, Rat
2D Structure
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SMILES / InChI / InChIKey
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
Compound class Endogenous peptide in human, mouse or rat
Ligand families/groups Neuropeptides
IUPAC Name
(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
INN number INN
8875 metenkefalin
Synonyms
1-5 Adrenorphin | [Met]-enkephalin | IRT-101 | methionine enkephalin | np2 enkephalin | opioid growth factor (OGF)
Gene/Precursor
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
BindingDB Ligand 50019056
CAS Registry No. 58569-55-4
ChEMBL Ligand CHEMBL13786
GtoPdb PubChem SID 135651808
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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Search UniChem for chemical match using the InChIKey YFGBQHOOROIVKG-FKBYEOEOSA-N
Search UniChem for chemicals with the same backbone YFGBQHOOROIVKG
UniProtKB P01210 (Hs), P22005 (Mm), P04094 (Rn)
Wikipedia Metenkefalin