Ergothioneine (CHEM021035)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 02:52:35 UTC
Update Date2016-10-28 10:02:23 UTC
Accession NumberCHEM021035
Identification
Common NameErgothioneine
ClassSmall Molecule
DescriptionA L-histidine derivative that is N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine in which the hydrogen at position 2 on the imdazole ring is replaced by a mercapto group. A naturally occurring metabolite of histidine synthesized by bacteria and fungi with antioxidant properties. It is found ubiquitously in plants and animals and is present in many human foodstuffs.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass229.299 g/mol
Monoisotopic Mass229.088 g/mol
CAS Registry NumberNot Available
IUPAC Name{5-[(2S)-2-carboxy-2-(trimethylazaniumyl)ethyl]-1H-imidazol-2-yl}sulfanide
Traditional Nameergothioneine
SMILESC[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.059 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-5910000000-5059c1d23a7b077f405fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-016r-9500000000-04f10497f2180ec7fad9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-da6c9ba163f2d8ff5693Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-3900000000-82fdfe23ca09b0ae98ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-002r-2920000000-1c6f86a16d521e0bbab6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-0900000000-9d0138913c95dbd5c498Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004i-3900000000-caa65ea3e411af866d82Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-052r-9830000000-0adc722312e2f3cf4a1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001r-0960000000-94c69f06737080f61979Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-1930000000-588cc28e89f864acdd3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0gdi-9850000000-40c5889b6855f1a4353eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001i-0290000000-81d6bfea2ae2d5d06472Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-052f-9000000000-28c8512538d456c43727Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0190000000-5bfc4fb56e55998326c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0960000000-7536b2e5a9447d8762e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-6900000000-9095b54dd80a9a95e5e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-0f87ac5b3b1e5f1dd7bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-5690000000-06e985e77495cc5c0e75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-e8772cee3888cb9ca84dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0980000000-10a32741360fe7b33d09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00b9-0900000000-0949d8b6748b0ffb9616Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-5900000000-4ddb7efd11211837e715Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-feef1aee555bb816227cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-5290000000-08d7e98139af1d46215bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-7900000000-e26a7c567169504547f2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003045
FooDB IDFDB004217
Phenol Explorer IDNot Available
KNApSAcK IDC00053098
BiGG IDNot Available
BioCyc IDCPD-15276
METLIN ID53
PDB IDNot Available
Wikipedia LinkErgothioneine
Chemspider ID4508619
ChEBI ID4828
PubChem Compound ID5351619
Kegg Compound IDC05570
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15030958
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15744438
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17616140
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18670092
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18841979
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19660151
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19911007
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20420449
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23418129
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23494799
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23922985
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24392160
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=25154712
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25736892
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=26079795
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=26149121
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=26229105
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=26338495
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=26412552
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=26542137
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=26579093
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=26634964
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=26713511
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=26772879
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=26774486
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=26921894
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=26994919
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=27101740
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=27134772
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=27306320
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=27444382
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=7144630
33. 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.
34. Xu, Jinzhu; Yadan, Jean Claude. Synthesis of L-(+)-Ergothioneine. Journal of Organic Chemistry (1995), 60(20), 6296-301.
35. 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.
36. 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.
37. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.