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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:28 UTC
Update Date2022-03-07 02:49:17 UTC
HMDB IDHMDB0003045
Secondary Accession Numbers
  • HMDB03045
Metabolite Identification
Common NameErgothioneine
DescriptionErgothioneine 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 ). 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 ). 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
Data?1582752261
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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+147.20430932474
DeepCCS[M-H]-144.84630932474
DeepCCS[M-2H]-178.44630932474
DeepCCS[M+Na]+153.3530932474
AllCCS[M+H]+147.932859911
AllCCS[M+H-H2O]+144.432859911
AllCCS[M+NH4]+151.132859911
AllCCS[M+Na]+152.132859911
AllCCS[M-H]-157.532859911
AllCCS[M+Na-2H]-158.532859911
AllCCS[M+HCOO]-159.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ErgothioneineC[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O2854.8Standard polar33892256
ErgothioneineC[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O1774.5Standard non polar33892256
ErgothioneineC[N+](C)(C)[C@@H](CC1=CNC(=S)N1)C([O-])=O2293.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ergothioneine,1TMS,isomer #1C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)[NH]1)C(=O)[O-]2009.7Semi standard non polar33892256
Ergothioneine,1TMS,isomer #1C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)[NH]1)C(=O)[O-]2095.4Standard non polar33892256
Ergothioneine,1TMS,isomer #1C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)[NH]1)C(=O)[O-]2651.5Standard polar33892256
Ergothioneine,1TMS,isomer #2C[N+](C)(C)[C@@H](CC1=C[NH]C(=S)N1[Si](C)(C)C)C(=O)[O-]1993.0Semi standard non polar33892256
Ergothioneine,1TMS,isomer #2C[N+](C)(C)[C@@H](CC1=C[NH]C(=S)N1[Si](C)(C)C)C(=O)[O-]2082.4Standard non polar33892256
Ergothioneine,1TMS,isomer #2C[N+](C)(C)[C@@H](CC1=C[NH]C(=S)N1[Si](C)(C)C)C(=O)[O-]2627.2Standard polar33892256
Ergothioneine,2TMS,isomer #1C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)N1[Si](C)(C)C)C(=O)[O-]2078.2Semi standard non polar33892256
Ergothioneine,2TMS,isomer #1C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)N1[Si](C)(C)C)C(=O)[O-]2161.8Standard non polar33892256
Ergothioneine,2TMS,isomer #1C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C(=S)N1[Si](C)(C)C)C(=O)[O-]2435.9Standard polar33892256
Ergothioneine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)[NH]C1=S2201.2Semi standard non polar33892256
Ergothioneine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)[NH]C1=S2328.4Standard non polar33892256
Ergothioneine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)[NH]C1=S2685.9Standard polar33892256
Ergothioneine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(C[C@@H](C(=O)[O-])[N+](C)(C)C)=C[NH]C1=S2170.9Semi standard non polar33892256
Ergothioneine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(C[C@@H](C(=O)[O-])[N+](C)(C)C)=C[NH]C1=S2336.0Standard non polar33892256
Ergothioneine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(C[C@@H](C(=O)[O-])[N+](C)(C)C)=C[NH]C1=S2653.6Standard polar33892256
Ergothioneine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)C1=S2489.6Semi standard non polar33892256
Ergothioneine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)C1=S2616.2Standard non polar33892256
Ergothioneine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)N([Si](C)(C)C(C)(C)C)C1=S2524.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ergothioneine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-5910000000-5059c1d23a7b077f405f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ergothioneine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 30V, Positive-QTOFsplash10-016r-9500000000-04f10497f2180ec7fad92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 40V, Positive-QTOFsplash10-014i-9100000000-da6c9ba163f2d8ff56932021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 20V, Positive-QTOFsplash10-004i-3900000000-82fdfe23ca09b0ae98ce2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 10V, Positive-QTOFsplash10-002r-2920000000-1c6f86a16d521e0bbab62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 35V, Positive-QTOFsplash10-004i-0900000000-9d0138913c95dbd5c4982021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 50V, Positive-QTOFsplash10-004i-3900000000-caa65ea3e411af866d822021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 10V, Positive-QTOFsplash10-052r-9830000000-0adc722312e2f3cf4a1a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 0V, Positive-QTOFsplash10-001r-0960000000-94c69f06737080f619792021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 10V, Positive-QTOFsplash10-000i-1930000000-588cc28e89f864acdd3d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 30V, Positive-QTOFsplash10-0gdi-9850000000-40c5889b6855f1a4353e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 0V, Positive-QTOFsplash10-001i-0290000000-81d6bfea2ae2d5d064722021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ergothioneine 30V, Positive-QTOFsplash10-052f-9000000000-28c8512538d456c437272021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 10V, Positive-QTOFsplash10-001i-0190000000-5bfc4fb56e55998326c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 20V, Positive-QTOFsplash10-01q9-0960000000-7536b2e5a9447d8762e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 40V, Positive-QTOFsplash10-0uxu-6900000000-9095b54dd80a9a95e5e02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 10V, Negative-QTOFsplash10-004i-0190000000-0f87ac5b3b1e5f1dd7bb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 20V, Negative-QTOFsplash10-004i-5690000000-06e985e77495cc5c0e752017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 40V, Negative-QTOFsplash10-0a4i-9000000000-e8772cee3888cb9ca84d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 10V, Positive-QTOFsplash10-001i-0980000000-10a32741360fe7b33d092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 20V, Positive-QTOFsplash10-00b9-0900000000-0949d8b6748b0ffb96162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 40V, Positive-QTOFsplash10-004i-5900000000-4ddb7efd11211837e7152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 10V, Negative-QTOFsplash10-004i-0090000000-feef1aee555bb816227c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 20V, Negative-QTOFsplash10-004j-5290000000-08d7e98139af1d46215b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ergothioneine 40V, Negative-QTOFsplash10-004j-7900000000-e26a7c567169504547f22021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.99 (0.84–1.52) uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1080351
References
Synthesis ReferenceXu, 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. 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 ]
  2. 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 ]
  3. 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. [PubMed:32033212 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Molecular weight:
62154.5