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Record Information
Version1.0
Creation Date2018-07-17 17:19:57 UTC
Update Date2020-05-11 20:42:56 UTC
MCDB ID BMDB0062216
Secondary Accession Numbers
  • BMDB62216
Metabolite Identification
Common NameErgothioneine
DescriptionErgothioneine, also known as sympectothion, 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. Ergothioneine is possibly soluble (in water) and a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
(2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoateChEBI
(AlphaS)-alpha-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner saltChEBI
(S)-(1-Carboxy-2-(2-mercaptoimidazol-4-yl)ethyl)trimethylammonium hydroxideChEBI
2-Mercaptohistidine trimethylbetaineChEBI
3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoateChEBI
Ergothioneine thiolChEBI
ErgothionineChEBI
ErythrothioneineChEBI
L-ErgothioneineChEBI
L-ThioneineChEBI
SympectothionChEBI
Thiolhistidine-betaineChEBI
ThiolhistidinebetaineChEBI
(2S)-3-(2-Mercapto-1H-imidazol-5-yl)-2-(trimethylammonio)propanoic acidGenerator
(AlphaS)-a-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner saltGenerator
(AlphaS)-α-carboxy-2,3-dihydro-N,N,N-trimethyl-2-thioxo-1H-imidazole-4-ethanaminium inner saltGenerator
3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acidGenerator
3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoateGenerator
3-(2-Sulphanylidene-1,3-dihydroimidazol-4-yl)-2-trimethylammonio-propanoic acidGenerator
2 Thiol L histidine betaineHMDB
2-Thiol-L-histidine-betaineHMDB
ThioneineHMDB
Chemical FormulaC9H15N3O2S
Average Molecular Weight229.299
Monoisotopic Molecular Weight229.088497429
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number497-30-3
SMILESNot Available
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
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Imidazole-2-thione
  • Azole
  • Imidazole
  • Quaternary ammonium salt
  • Heteroaromatic compound
  • Tetraalkylammonium salt
  • Thiourea
  • Carboxylic acid salt
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organosulfur compound
  • Organic oxide
  • Organic salt
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0003045
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004217
KNApSAcK IDC00053098
Chemspider ID4508619
KEGG Compound IDC05570
BioCyc IDCPD-15276
BiGG IDNot Available
Wikipedia LinkErgothioneine
METLIN ID53
PubChem Compound5351619
PDB IDNot Available
ChEBI ID4828
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]