Showing metabocard for Ergothioneine (BMDB0062216)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-07-17 17:19:57 UTC
Update Date2020-05-11 20:42:56 UTC
BMDB IDBMDB0062216
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
MOLSDFPDBSMILESInChI
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 Name{5-[(2S)-2-carboxy-2-(trimethylazaniumyl)ethyl]-1H-imidazol-2-yl}sulfanide
Traditional Nameergothioneine
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
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
Ontology
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.7ALOGPS
logP-4ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)5.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.69 m³·mol⁻¹ChemAxon
Polarizability23.5 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003045
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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)Not Available
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 ]