1.0 2010-04-08 22:06:08 UTC 2025-11-18 22:55:33 UTC FDB004217 Ergothioneine 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 (PMID: 15795384). 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. (2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate (2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoic acid (AlphaS)-a-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt (AlphaS)-alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner salt (AlphaS)-α-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-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 C9H16N3O2S 230.307 230.096322461 [1-carboxy-2-(2-sulfanyl-1H-imidazol-5-yl)ethyl]trimethylazanium [1-carboxy-2-(2-sulfanyl-3H-imidazol-4-yl)ethyl]trimethylazanium 497-30-3 C[N+](C)(C)C(CC1=CNC(=S)N1)C(O)=O 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)/p+1 SSISHJJTAXXQAX-UHFFFAOYSA-O belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Histidine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic heteromonocyclic compounds Alpha amino acids Aralkylamines Azacyclic compounds Carbonyl compounds Carboxylic acids Heteroaromatic compounds Hydrocarbon derivatives Imidazoles Imidazolethiones Monocarboxylic acids and derivatives Organic cations Organic oxides Organic salts Organopnictogen compounds Tetraalkylammonium salts Thioureas Alpha-amino acid Amine Aralkylamine Aromatic heteromonocyclic compound Azacycle Azole Carbonyl group Carboxylic acid Heteroaromatic compound Histidine or derivatives Hydrocarbon derivative Imidazole Imidazole-2-thione Monocarboxylic acid or derivatives Organic cation Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Quaternary ammonium salt Tetraalkylammonium salt Thiourea Solid logp -0.27 ALOGPS logs -3.83 ALOGPS solubility 3.94e-02 g/l ALOGPS logp -4 ChemAxon pka_strongest_acidic 1.88 ChemAxon pka_strongest_basic 5.31 ChemAxon iupac [1-carboxy-2-(2-sulfanyl-1H-imidazol-5-yl)ethyl]trimethylazanium ChemAxon average_mass 230.307 ChemAxon mono_mass 230.096322461 ChemAxon smiles C[N+](C)(C)C(CC1=CNC(=S)N1)C(O)=O ChemAxon formula C9H16N3O2S ChemAxon 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)/p+1 ChemAxon inchikey SSISHJJTAXXQAX-UHFFFAOYSA-O ChemAxon polar_surface_area 65.98 ChemAxon refractivity 71.52 ChemAxon polarizability 23.84 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 1 ChemAxon formal_charge 1 ChemAxon HMDB03045 #<Reference:0x000055ce3079f0a0> #<Reference:0x000055ce3079eee8> Milk (Cow) Type 2 specific Oat Type 1 specific Avena sativa 4498 Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.