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CHEBI:4828 - ergothioneine

ChEBI IDCHEBI:4828
ChEBI Nameergothioneine
Stars
DefinitionA 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 synthesized by bacteria and fungi with antioxidant properties. It is found ubiquitously in plants and animals and is present in many human foodstuffs.
Last Modified9 December 2024
DownloadsMolfile
FormulaC9H15N3O2S
Net Charge0
Average Mass229.305
Monoisotopic Mass229.08850
SMILESC[N+](C)(C)[C@@H](Cc1cnc(S)n1)C(=O)[O-]
InChIInChI=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
InChIKeySSISHJJTAXXQAX-ZETCQYMHSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Mycobacterium tuberculosis (ncbitaxon:1773) - PubMed (26774486)
Pleurotus ostreatus (ncbitaxon:5322) - PubMed (27134772)
Coprinus comatus (ncbitaxon:56187) - PubMed (26338495)
Roles Classification
Chemical Roles:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
chelator  A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
xenobiotic metabolite  Any metabolite produced by metabolism of a xenobiotic compound.
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.
ChEBI Ontology
Outgoing Relation(s)
ergothioneine (CHEBI:4828) has role antioxidant (CHEBI:22586)
ergothioneine (CHEBI:4828) has role chelator (CHEBI:38161)
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 a sulfur-containing amino acid (CHEBI:26834)
ergothioneine (CHEBI:4828) is conjugate base of ergothioneine(1+) (CHEBI:134344)
ergothioneine (CHEBI:4828) is tautomer of ergothioneine thione form (CHEBI:82707)
Incoming Relation(s)
S-methyl-L-ergothioneine (CHEBI:76620) has functional parent ergothioneine (CHEBI:4828)
2-sulfenohercynine (CHEBI:136834) has functional parent ergothioneine (CHEBI:4828)
ergothioneine(1+) (CHEBI:134344) is conjugate acid of 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  Source
L-ergothioneineChemIDplus
erythrothioneineChEBI
thiolhistidinebetaineChEBI
2-mercaptohistidine trimethylbetaineChEBI
sympectothionChemIDplus
3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoateChEBI
Manual XrefsDatabases
C05570KEGG COMPOUND
HMDB0003045HMDB
CPD-15276MetaCyc
ErgothioneineWikipedia
Registry NumbersSources
Reaxys:8411606Reaxys
Reaxys:5755696Reaxys
CAS:497-30-3KEGG COMPOUND
CAS:497-30-3ChemIDplus
Citations