ergothioneine (CHEBI:4828)

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ChEBI Name	ergothioneine

ChEBI ID	CHEBI:4828

Definition	A L-histidine derivative that is N^α,N^α,N^α-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

Average Mass

229.29900

Monoisotopic Mass

229.08850

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:txid1773)	See: PubMed
Pleurotus ostreatus (NCBI:txid5322)	See: PubMed
Coprinus comatus (NCBI:txid56187)	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 base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) 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.

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
(αS)-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

Last Modified

05 July 2017