1.02010-04-08 22:06:08 UTC2019-11-26 02:59:53 UTCFDB004217ErgothioneineA 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 hydroxide2-Mercaptohistidine trimethylbetaine2-Thiol-L-histidine-betaine3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acid3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoate3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acidErgothioneine thiolErgothionineErythrothioneineL-ergothioneineL-thioneineSympectothionThiolhistidine-betaineThiolhistidinebetaineThioneineC9H16N3O2S230.307230.096322461[1-carboxy-2-(2-sulfanyl-1H-imidazol-5-yl)ethyl]trimethylazanium[1-carboxy-2-(2-sulfanyl-3H-imidazol-4-yl)ethyl]trimethylazanium497-30-3C[N+](C)(C)C(CC1=CNC(=S)N1)C(O)=OInChI=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+1SSISHJJTAXXQAX-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 derivativesOrganic compoundsOrganic acids and derivativesCarboxylic acids and derivativesAmino acids, peptides, and analoguesAromatic heteromonocyclic compoundsAlpha amino acidsAralkylaminesAzacyclic compoundsCarbonyl compoundsCarboxylic acidsHeteroaromatic compoundsHydrocarbon derivativesImidazolesImidazolethionesMonocarboxylic acids and derivativesOrganic cationsOrganic oxidesOrganic saltsOrganopnictogen compoundsTetraalkylammonium saltsThioureasAlpha-amino acidAmineAralkylamineAromatic heteromonocyclic compoundAzacycleAzoleCarbonyl groupCarboxylic acidHeteroaromatic compoundHistidine or derivativesHydrocarbon derivativeImidazoleImidazole-2-thioneMonocarboxylic acid or derivativesOrganic cationOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic saltOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOrganosulfur compoundQuaternary ammonium saltTetraalkylammonium saltThioureaSolidlogp-0.27logs-3.83solubility3.94e-02 g/llogp-4pka_strongest_acidic1.88pka_strongest_basic5.31iupac[1-carboxy-2-(2-sulfanyl-1H-imidazol-5-yl)ethyl]trimethylazaniumaverage_mass230.307mono_mass230.096322461smilesC[N+](C)(C)C(CC1=CNC(=S)N1)C(O)=OformulaC9H16N3O2SinchiInChI=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+1inchikeySSISHJJTAXXQAX-UHFFFAOYSA-Opolar_surface_area65.98refractivity71.52polarizability23.84rotatable_bond_count4acceptor_count3donor_count3physiological_charge1formal_charge1HMDB03045#<Reference:0x0000555675a55318>#<Reference:0x0000555675a55160>Milk (Cow)Type 2specificOatType 1specificAvena sativa4498antioxidant502A 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.