CHEBI:4828 - ergothioneine

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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 synthesized by bacteria and fungi with antioxidant properties. It is found ubiquitously in plants and animals and is present in many human foodstuffs.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C9H15N3O2S
Net Charge 0
Average Mass 229.29900
Monoisotopic Mass 229.088
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
Metabolite of Species Details
Mycobacterium tuberculosis (NCBI:1773) See: PubMed
Pleurotus ostreatus (NCBI:5322) See: PubMed
Coprinus comatus (NCBI:56187) See: PubMed
Roles Classification
Chemical Role(s): 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 acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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 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 2-sulfenohercynine (CHEBI:136834) has functional parent ergothioneine (CHEBI:4828)
S-methyl-L-ergothioneine (CHEBI:76620) 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 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
HMDB0003045 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
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Last Modified
05 July 2017