CHEBI:17515 - L-γ-glutamyl-L-cysteine

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ChEBI Name L-γ-glutamyl-L-cysteine
ChEBI ID CHEBI:17515
ChEBI ASCII Name L-gamma-glutamyl-L-cysteine
Definition A molecular entity formed when L-cysteine amino group binds to the γ-carbonyl of L-glutamic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:39975, CHEBI:10566, CHEBI:10570, CHEBI:12400, CHEBI:12404, CHEBI:17971, CHEBI:24185, CHEBI:24194
Supplier Information eMolecules:537269, ZINC000004543724
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Docosatetraenoic acid designates any straight chain 22:4 fatty acid. (See Essential fatty acid for nomenclature.) One isomer is of particular interest: all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the common name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain. This unsaturated fatty acid is also metabolized by cells to biologically active products viz., dihomoprostaglandins, and epoxydocosatrienoic acids (EDTs, also known as dihomo-EETs). In addition to being endothelium-derived hyperpolarizing factors, EDTs have demonstrated anti-endoplasmic reticulum stress and anti-nociceptive activities. They are hydrolyzed by the soluble epoxide hydrolase (sEH) to dihydroxydocosatrienoic acids (DHDTs) and hence might play a role in the efficacy of sEH inhibitors.
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Formula C8H14N2O5S
Net Charge 0
Average Mass 250.27324
Monoisotopic Mass 250.06234
InChI InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
InChIKey RITKHVBHSGLULN-WHFBIAKZSA-N
SMILES N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) 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): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing L-γ-glutamyl-L-cysteine (CHEBI:17515) has functional parent L-cysteine (CHEBI:17561)
L-γ-glutamyl-L-cysteine (CHEBI:17515) has functional parent L-glutamic acid (CHEBI:16015)
L-γ-glutamyl-L-cysteine (CHEBI:17515) has role Escherichia coli metabolite (CHEBI:76971)
L-γ-glutamyl-L-cysteine (CHEBI:17515) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
L-γ-glutamyl-L-cysteine (CHEBI:17515) has role human metabolite (CHEBI:77746)
L-γ-glutamyl-L-cysteine (CHEBI:17515) has role mouse metabolite (CHEBI:75771)
L-γ-glutamyl-L-cysteine (CHEBI:17515) is a gamma-glutamylcysteine (CHEBI:24195)
L-γ-glutamyl-L-cysteine (CHEBI:17515) is conjugate acid of L-γ-glutamyl-L-cysteinate(1−) (CHEBI:58173)
Incoming DON-10-gamma-glutamylcysteine (CHEBI:149450) has functional parent L-γ-glutamyl-L-cysteine (CHEBI:17515)
L-γ-glutamyl-L-cysteinate(1−) (CHEBI:58173) is conjugate base of L-γ-glutamyl-L-cysteine (CHEBI:17515)
IUPAC Name
L-γ-glutamyl-L-cysteine
Synonyms Sources
5-L-Glutamyl-L-cysteine KEGG COMPOUND
gamma-Glu-Cys ChEBI
gamma-Glutamylcysteine KEGG COMPOUND
gamma-L-Glutamyl-L-cysteine KEGG COMPOUND
γGluCys ChEBI
Glu(-Cys) JCBN
L-gamma-glutamyl-L-cysteine PDBeChem
L-gamma-Glutamylcysteine KEGG COMPOUND
Manual Xrefs Databases
C00007507 KNApSAcK
C00669 KEGG COMPOUND
DB03408 DrugBank
Gamma-Glutamylcysteine Wikipedia
HMDB0001049 HMDB
L-GAMMA-GLUTAMYLCYSTEINE MetaCyc
View more database links
Registry Numbers Types Sources
1729154 Reaxys Registry Number Reaxys
636-58-8 CAS Registry Number ChemIDplus
Citation Type Source
11409324 PubMed citation Europe PMC
Last Modified
27 January 2016