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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-5910000000-5059c1d23a7b077f405fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-016r-9500000000-04f10497f2180ec7fad9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-da6c9ba163f2d8ff5693View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-3900000000-82fdfe23ca09b0ae98ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-002r-2920000000-1c6f86a16d521e0bbab6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-0900000000-9d0138913c95dbd5c498View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004i-3900000000-caa65ea3e411af866d82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-052r-9830000000-0adc722312e2f3cf4a1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001r-0960000000-94c69f06737080f61979View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-1930000000-588cc28e89f864acdd3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0gdi-9850000000-40c5889b6855f1a4353eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001i-0290000000-81d6bfea2ae2d5d06472View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-052f-9000000000-28c8512538d456c43727View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0190000000-5bfc4fb56e55998326c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0960000000-7536b2e5a9447d8762e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-6900000000-9095b54dd80a9a95e5e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-0f87ac5b3b1e5f1dd7bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5690000000-06e985e77495cc5c0e75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-e8772cee3888cb9ca84dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0980000000-10a32741360fe7b33d09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00b9-0900000000-0949d8b6748b0ffb9616View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-4ddb7efd11211837e715View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-feef1aee555bb816227cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-5290000000-08d7e98139af1d46215bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-7900000000-e26a7c567169504547f2View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
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 ]