Human Metabolome Database Version 3.5

Showing metabocard for Ergothioneine (HMDB03045)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:28 -0600
Update Date 2013-05-29 13:37:18 -0600
HMDB ID HMDB03045
Secondary Accession Numbers None
Metabolite Identification
Common Name Ergothioneine
Description 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 Link_out). 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 Link_out). 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Ergothionine
  2. L-Ergothioneine
  3. L-Thioneine
  4. Sympectothion
  5. Thiolhistidine-betaine
Chemical Formula C9H15N3O2S
Average Molecular Weight 229.299
Monoisotopic Molecular Weight 229.088497429
IUPAC Name (2S)-3-(2-sulfanylidene-2,3-dihydro-1H-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
Traditional IUPAC Name (2S)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylaminio)propanoate
CAS Registry Number 497-30-3
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 Key SSISHJJTAXXQAX-ZETCQYMHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha 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 Parent Alpha Amino Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Plant
Biofunction
  • Lipid catabolism, Fatty acid transport, Energy production
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.059 g/L ALOGPS
LogP -1.72 ALOGPS
LogP -4 ChemAxon
LogS -3.68 ALOGPS
pKa (strongest acidic) 2.49 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 64.19 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 84.87 ChemAxon
Polarizability 23.43 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB004217
KNApSAcK ID Not Available
Chemspider ID 4508619 Link_out
KEGG Compound ID C05570 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03045 Link_out
Metagene Link HMDB03045 Link_out
METLIN ID 53 Link_out
PubChem Compound 5351619 Link_out
PDB ID Not Available
ChEBI ID 4828 Link_out
References
Synthesis Reference Xu, 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. 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 Link_out
  2. 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 Link_out

Transporters
Name: Solute carrier family 22 member 4
Reactions: Not Available
Gene Name: SLC22A4
Uniprot ID: Q9H015 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA