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CHEBI:6618 - Met-enkephalin

ChEBI IDCHEBI:6618
ChEBI NameMet-enkephalin
Stars
DefinitionA pentapeptide comprising L-tyrosine, glycine, glycine, L-phenylalanine and L-methionine residues joined in sequence by peptide linkages. It is an endogenous opioid peptide with antitumor, analgesic, and immune-boosting properties.
Last Modified3 March 2022
DownloadsMolfile
FormulaC27H35N5O7S
Net Charge0
Average Mass573.672
Monoisotopic Mass573.22572
SMILESCSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O
InChIInChI=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
InChIKeyYFGBQHOOROIVKG-FKBYEOEOSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
delta-opioid receptor agonist  A compound that exhibits agonist activity at the δ-opioid receptor.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mu-opioid receptor agonist  A compound that exhibits agonist activity at the μ-opioid receptor.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
delta-opioid receptor agonist  A compound that exhibits agonist activity at the δ-opioid receptor.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
mu-opioid receptor agonist  A compound that exhibits agonist activity at the μ-opioid receptor.
ChEBI Ontology
Outgoing Relation(s)
Met-enkephalin (CHEBI:6618) has functional parent L-methionine (CHEBI:16643)
Met-enkephalin (CHEBI:6618) has functional parent L-phenylalanine (CHEBI:17295)
Met-enkephalin (CHEBI:6618) has functional parent L-tyrosine (CHEBI:17895)
Met-enkephalin (CHEBI:6618) has functional parent glycine (CHEBI:15428)
Met-enkephalin (CHEBI:6618) has role analgesic (CHEBI:35480)
Met-enkephalin (CHEBI:6618) has role antineoplastic agent (CHEBI:35610)
Met-enkephalin (CHEBI:6618) has role human metabolite (CHEBI:77746)
Met-enkephalin (CHEBI:6618) has role δ-opioid receptor agonist (CHEBI:64054)
Met-enkephalin (CHEBI:6618) has role μ-opioid receptor agonist (CHEBI:55322)
Met-enkephalin (CHEBI:6618) is a pentapeptide (CHEBI:48545)
Met-enkephalin (CHEBI:6618) is tautomer of Met-enkephalin zwitterion (CHEBI:189868)
Incoming Relation(s)
Met-enkephalin zwitterion (CHEBI:189868) is tautomer of Met-enkephalin (CHEBI:6618)
IUPAC Name 
L-tyrosylglycylglycyl-L-phenylalanyl-L-methionine
INNs  Source
metencefalinaWHO MedNet
metenkefalinWHO MedNet
métenkefalineWHO MedNet
metenkefalinumWHO MedNet
Synonyms  Source
MET-enkephalinKEGG COMPOUND
methionine enkephalinKEGG COMPOUND
H-L-Tyr-Gly-Gly-L-Phe-L-Met-OHChEBI
Tyr-Gly-Gly-Phe-MetChemIDplus
L-Tyr-Gly-Gly-L-Phe-L-MetChemIDplus
Tyr-Gly-Gly-Phe-Met-OHChemIDplus
Brand Name  Source
LupexChemIDplus
Manual XrefsDatabases
C11684KEGG COMPOUND
DB12668DrugBank
391597ChemSpider
Met-enkephalinWikipedia
Registry NumbersSources
CAS:58569-55-4ChemIDplus
Citations