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Record Information
Version3.6
Creation Date2006-05-22 15:12:28 UTC
Update Date2013-05-29 19:37:18 UTC
HMDB IDHMDB03045
Secondary Accession NumbersNone
Metabolite Identification
Common NameErgothioneine
DescriptionErgothioneine 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 (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.
Structure
Thumb
Synonyms
  1. Ergothionine
  2. L-Ergothioneine
  3. L-Thioneine
  4. Sympectothion
  5. Thiolhistidine-betaine
Chemical FormulaC9H15N3O2S
Average Molecular Weight229.299
Monoisotopic Molecular Weight229.088497429
IUPAC Name(2S)-3-(2-sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
Traditional Name(2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylaminio)propanoate
CAS Registry Number497-30-3
SMILES
C[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O
InChI Identifier
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
InChI KeySSISHJJTAXXQAX-ZETCQYMHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
Substituents
  • Arylthiol
  • Carboxylic Acid Salt
  • Imidazole
  • Imidazolyl Carboxylic Acid Derivative
  • Quaternary Ammonium Salt
  • Thiol (Sulfanyl Compound)
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Plant
Biofunction
  • Lipid catabolism, Fatty acid transport, Energy production
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.059 g/LALOGPS
logP-1.7ALOGPS
logP-4ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.19ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.87ChemAxon
Polarizability23.43ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB004217
KNApSAcK IDNot Available
Chemspider ID4508619
KEGG Compound IDC05570
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03045
Metagene LinkHMDB03045
METLIN ID53
PubChem Compound5351619
PDB IDNot Available
ChEBI ID4828
References
Synthesis ReferenceXu, Jinzhu; Yadan, Jean Claude. Synthesis of L-(+)-Ergothioneine. Journal of Organic Chemistry (1995), 60(20), 6296-301.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Grundemann D, Harlfinger S, Golz S, Geerts A, Lazar A, Berkels R, Jung N, Rubbert A, Schomig E: Discovery of the ergothioneine transporter. Proc Natl Acad Sci U S A. 2005 Apr 5;102(14):5256-61. Epub 2005 Mar 28. Pubmed: 15795384
  2. OHARA M, TOMITA K, WATANABE R, KONO K, WATANABE K: Estimation of ergothioneine in urine, blood and organs by determination of the alkaline perhydrol-labile sulfur. Jpn J Med Sci Biol. 1952 Oct;5(5):259-63. Pubmed: 13034359

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Molecular weight:
62154.5