S-methyl-L-ergothioneine (CHEBI:76620)

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CHEBI:76620 - S-methyl-L-ergothioneine

ChEBI ID	CHEBI:76620
ChEBI Name	S-methyl-L-ergothioneine
Stars
ASCII Name	S-methyl-L-ergothioneine
Definition	An amino acid betaine that is ergothioneine in which the hydrogen attached to the sulfur is replaced by a methyl group. It has been isolated from the deepwater (500-1,600 m) marine sponge Macandrewia azorica.
Secondary ChEBI ID	CHEBI:90131
Last Modified	19 June 2025
Submitter	Gareth Owen, mwilliams
Downloads	Molfile

Formula	C10H17N3O2S
Net Charge	0
Average Mass	243.332
Monoisotopic Mass	243.10415
SMILES	CSc1ncc(C[C@@H](C(=O)[O-])[N+](C)(C)C)n1
InChI	InChI=1S/C10H17N3O2S/c1-13(2,3)8(9(14)15)5-7-6-11-10(12-7)16-4/h6,8H,5H2,1-4H3,(H-,11,12,14,15)/t8-/m0/s1
InChIKey	GVQNHIYBRMFCMS-QMMMGPOBSA-N

Species of Metabolite	Component	Source
Macandrewia azorica (ncbitaxon:1562495)	-	PubMed (15340692)
Mus musculus (ncbitaxon:10090)
	-	MetaboLights (MTBLS126)
	-	MetaboLights (MTBLS87)
	-	DOI (10.1371/journal.pone.0115359)
	-	MetaboLights (MTBLS88)
	-	MetaboLights (MTBLS125)

Roles Classification

Biological Roles:

animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.

marine metabolite Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.

ChEBI Ontology

Outgoing Relation(s)
	S-methyl-L-ergothioneine (CHEBI:76620) has functional parent ergothioneine (CHEBI:4828)
	S-methyl-L-ergothioneine (CHEBI:76620) has role animal metabolite (CHEBI:75767)
	S-methyl-L-ergothioneine (CHEBI:76620) has role marine metabolite (CHEBI:76507)
	S-methyl-L-ergothioneine (CHEBI:76620) is a amino-acid betaine (CHEBI:22860)
	S-methyl-L-ergothioneine (CHEBI:76620) is a imidazoles (CHEBI:24780)
	S-methyl-L-ergothioneine (CHEBI:76620) is a methyl sulfide (CHEBI:86315)

IUPAC Names
(2S)-3-[2-(methylsulfanyl)-1H-imidazol-4-yl]-2-(trimethylammonio)propanoate
(2S)-3-(2-methylsulfanyl-1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate

Synonyms	Source
S-methylergothioneine	ChEBI
(2S)-3-[2-(methylsulfanyl)-1H-imidazol-4-yl]-2-(trimethylammonio)propionate	ChEBI
(+)-S-methylergothioneine	ChEBI
(+)-L-methylergothioneine	ChEBI
(+)-S-methyl-L-ergothioneine	ChEBI
7S-(+)-methylergothioneine	ChEBI

UniProt Name	Source
S-methyl-L-ergothioneine	UniProt

Citations