General Information of MET (ID: META00838)
Name Ergothioneine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate; (2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoic acid; (AlphaS)-alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt; (S)-(1-Carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethylammonium hydroxide; 2 Thiol L histidine betaine; 2-Mercaptohistidine trimethylbetaine; 2-Thiol-L-histidine-betaine; 3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate; 3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acid; 3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate; 3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acid; Ergothioneine thiol; Ergothionine; Erythrothioneine; L-Ergothioneine; L-Thioneine; Sympectothion; Thiolhistidine-betaine; Thiolhistidinebetaine; Thioneine
Source Food
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
5351619
HMDB ID
HMDB0003045
Formula
C9H15N3O2S
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C05570
ChEBI ID
4828
FooDB ID
FDB004217
ChemSpider ID
4508619
METLIN ID
53
Physicochemical Properties Molecular Weight 229.3 Topological Polar Surface Area 96.3
XlogP 0.3 Complexity 314
Heavy Atom Count 15 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
Ergothioneine is a naturally occurring metabolite of histidine that has antioxidant properties. -- Pubchem. Ergothioneine is a product of plant origin that accumulates in animal tissues. Ergothioneine is biosynthesized exclusively by fungi and mycobacteria and is captured by plants through their roots. As an ingredient of human food, ET is distributed very unevenly. By far, the highest levels of Ergothioneine have been found in mushrooms (0.1-1 mg/g dried material). Ergothioneine is rapidly cleared from the circulation and then avidly retained with minimal metabolism: the whole-body half-life of ingested Ergothioneine in rats is 1 month. The content of Ergothioneine varies greatly among tissues and is strongly dependent on its dietary level. In addition to erythrocytes and bone marrow, high Ergothioneine levels have also been found in seminal fluid. The precise physiological role of ET has remained elusive since its discovery in 1909. It is known that Ergothioneine is a powerful scavenger of hydroxyl radicals and an inhibitor of iron or copper ion-dependent generation of hydroxyl radicals from hydrogen peroxide (H2O2). A specific ergothioneine transporter has recently been identified (gene symbol SLC22A4 - PMID: 15795384). Ergothioneine appears to play a pivotal protective role in monocytes, because the occurrence of rheumatoid arthritis and Crohn's disease has very recently been linked to variant ergothioneine transporter genes. SLC22A4 is highly expressed in the kidney, where it is thought to aid in active secretion of organic cations, and may facilitate the active reabsorption of ergothioneine.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Transcriptional coactivator (TC)
            PPAR-gamma coactivator 1-alpha (PPARGC1A) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of Ppargc1a
                      Induced Change Ergothioneine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Congestive heart failure [ICD-11: BD10]
                      Details It is reported that knockout of Ppargc1a leads to the decrease of ergothioneine levels compared with control group.
References
1 Heart specific PGC-1 deletion identifies metabolome of cardiac restricted metabolic heart failure. Cardiovasc Res. 2019 Jan 1;115(1):107-118.

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