CHEBI:89656 - Leu-enkephalin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name Leu-enkephalin
ChEBI ID CHEBI:89656
Definition A pentapeptide comprising L-tyrosine, glycine, glycine, L-phenylalanine and L-leucine residues joined in sequence by peptide linkages. It is an endogenous opioid peptide produced in vertebrate species, including rodents, primates and humans that results from decomposition of proenkephalin or dynorphin and exhibits antinociceptive properties.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:80263
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C28H37N5O7
Net Charge 0
Average Mass 555.632
Monoisotopic Mass 555.26930
InChI InChI=1S/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1
InChIKey URLZCHNOLZSCCA-VABKMULXSA-N
SMILES CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC1=CC=C(O)C=C1)C(O)=O
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) Found in blood plasma (BTO_0000131). See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): delta-opioid receptor agonist
A compound that exhibits agonist activity at the delta-opioid receptor.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
neurotransmitter
An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.
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).
rat metabolite
Any mammalian metabolite produced during a metabolic reaction in rat (Rattus norvegicus).
Application(s): delta-opioid receptor agonist
A compound that exhibits agonist activity at the delta-opioid receptor.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing Leu-enkephalin (CHEBI:89656) has functional parent L-leucine (CHEBI:15603)
Leu-enkephalin (CHEBI:89656) has functional parent L-phenylalanine (CHEBI:17295)
Leu-enkephalin (CHEBI:89656) has functional parent L-tyrosine (CHEBI:17895)
Leu-enkephalin (CHEBI:89656) has functional parent glycine (CHEBI:15428)
Leu-enkephalin (CHEBI:89656) has role δ-opioid receptor agonist (CHEBI:64054)
Leu-enkephalin (CHEBI:89656) has role μ-opioid receptor agonist (CHEBI:55322)
Leu-enkephalin (CHEBI:89656) has role analgesic (CHEBI:35480)
Leu-enkephalin (CHEBI:89656) has role human metabolite (CHEBI:77746)
Leu-enkephalin (CHEBI:89656) has role neurotransmitter (CHEBI:25512)
Leu-enkephalin (CHEBI:89656) has role rat metabolite (CHEBI:86264)
Leu-enkephalin (CHEBI:89656) is a pentapeptide (CHEBI:48545)
Leu-enkephalin (CHEBI:89656) is tautomer of Leu-enkephalin zwitterion (CHEBI:190689)
Incoming Leu-enkephalin zwitterion (CHEBI:190689) is tautomer of Leu-enkephalin (CHEBI:89656)
IUPAC Name
L-tyrosylglycylglycyl-L-phenylalanyl-L-leucine
Synonyms Sources
(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid HMDB
[5-Leucine]enkephalin HMDB
[Leu5]-enkephalin HMDB
[Leu5]enkephalin HMDB
[Leu]enkephalin ChEBI
enkephalin L HMDB
enkephalin, leucine ChemIDplus
H-Tyr-Gly-Gly-Phe-Leu-OH ChEBI
L-ENK ChEBI
L-Tyr-Gly-Gly-L-Phe-L-Leu ChEBI
Leu-ENK ChEBI
Leu-enkephalin ChemIDplus
leucine enkephalin ChemIDplus
leucine-enkephalin ChemIDplus
leucyl-enkephalin ChemIDplus
LeuENK ChEBI
N-(N-(N-(N-L-tyrosylglycyl)glycyl)-L-phenylalanyl)-L-leucine ChemIDplus
Tyr-Gly-Gly-Phe-Leu ChEBI
Tyr-Gly-Gly-Phe-Leu-OH ChEBI
Y-G-G-F-L ChEBI
YGGFL ChEBI
Manual Xrefs Databases
406229 ChemSpider
C16041 KEGG COMPOUND
FDB022389 FooDB
HMDB0001045 HMDB
Leu-enkephalin Wikipedia
View more database links
Registry Numbers Types Sources
3582445 Reaxys Registry Number Reaxys
58822-25-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16802191 PubMed citation Europe PMC
20161518 PubMed citation Europe PMC
20669325 PubMed citation Europe PMC
22323423 PubMed citation Europe PMC
23661424 PubMed citation Europe PMC
23912034 PubMed citation Europe PMC
24480726 PubMed citation Europe PMC
2583565 PubMed citation Europe PMC
26723675 PubMed citation Europe PMC
26763532 PubMed citation Europe PMC
28233882 PubMed citation Europe PMC
28382489 PubMed citation Europe PMC
29351722 PubMed citation Europe PMC
29648788 PubMed citation Europe PMC
29793486 PubMed citation Europe PMC
29981318 PubMed citation Europe PMC
30014064 PubMed citation Europe PMC
30234204 PubMed citation Europe PMC
31843219 PubMed citation Europe PMC
32556047 PubMed citation Europe PMC
32961052 PubMed citation Europe PMC
33389463 PubMed citation Europe PMC
33573373 PubMed citation Europe PMC
33663067 PubMed citation Europe PMC
4069309 PubMed citation Europe PMC
9450624 PubMed citation Europe PMC
Last Modified
03 March 2022