CHEBI:4828 - ergothioneine

Main ChEBI Ontology Automatic Xrefs
ChEBI Name ergothioneine
ChEBI ID CHEBI:4828
Definition A L-histidine derivative that is Nα,Nα,Nα-trimethyl-L-histidine in which the hydrogen at position 2 on the imdazole ring is replaced by a mercapto group. A naturally occurring metabolite of histidine with antioxidant properties; abundant in most plants and animals, obtained in animals through the diet.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C9H15N3O2S
Net Charge 0
Average Mass 229.29900
InChI InChI=1S/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1
InChIKey SSISHJJTAXXQAX-ZETCQYMHSA-N
SMILES C[N+](C)(C)[C@@H](Cc1c[nH]c(S)n1)C([O-])=O
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.
Biological Role(s): fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
xenobiotic metabolite
Any metabolite produced by metabolism of a xenobiotic compound.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ergothioneine (CHEBI:4828) has role antioxidant (CHEBI:22586)
ergothioneine (CHEBI:4828) has role fungal metabolite (CHEBI:76946)
ergothioneine (CHEBI:4828) has role plant metabolite (CHEBI:76924)
ergothioneine (CHEBI:4828) has role xenobiotic metabolite (CHEBI:76206)
ergothioneine (CHEBI:4828) is a L-histidine derivative (CHEBI:84076)
ergothioneine (CHEBI:4828) is a amino-acid betaine (CHEBI:22860)
ergothioneine (CHEBI:4828) is tautomer of ergothioneine thione form (CHEBI:82707)
Incoming S-methyl-L-ergothioneine (CHEBI:76620) has functional parent ergothioneine (CHEBI:4828)
ergothioneine thione form (CHEBI:82707) is tautomer of ergothioneine (CHEBI:4828)
IUPAC Name
(2S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate
Synonyms Sources
(2S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate ChEBI
S)-α-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt ChEBI
(S)-(1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethylammonium hydroxide ChemIDplus
2-mercaptohistidine trimethylbetaine ChEBI
3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate ChEBI
ergothioneine thiol UniProt
ergothionine ChemIDplus
erythrothioneine ChEBI
L-ergothioneine ChemIDplus
L-thioneine ChemIDplus
sympectothion ChemIDplus
thiolhistidine-betaine ChemIDplus
thiolhistidinebetaine ChEBI
Database Links Databases
C05570 KEGG COMPOUND
CPD-15276 MetaCyc
Ergothioneine Wikipedia
HMDB03045 HMDB
View more database links
Registry Numbers Types Sources
497-30-3 CAS Registry Number ChemIDplus
5755696 Reaxys Registry Number Reaxys
5755696 Beilstein Registry Number Beilstein
8411606 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17616140 PubMed citation CiteXplore
18670092 PubMed citation CiteXplore
18841979 PubMed citation CiteXplore
Last Modified
07 January 2015