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ergothioneine

Go to external page http://purl.obolibrary.org/obo/CHEBI_4828

A L-histidine derivative that is N(alpha),N(alpha),N(alpha)-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.

Term info

Label

ergothioneine

Synonyms
  • (2S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate
database cross reference
Subsets

3_STAR

IUPAC NAME
(2S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate [ IUPAC ]

charge

0

formula

C9H15N3O2S

has obo namespace

chebi_ontology

has related synonym

L-ergothioneine, (2S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate, 2-mercaptohistidine trimethylbetaine, thiolhistidinebetaine, 3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate, ergothioneine thiol, sympectothion, L-thioneine, (S)-(1-carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethylammonium hydroxide, erythrothioneine, ergothionine, (alphaS)-alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt, thiolhistidine-betaine

id

CHEBI:4828

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

mass

229.29900

monoisotopicmass

229.08850

smiles

C[N+](C)(C)[C@@H](Cc1c[nH]c(S)n1)C([O-])=O