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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 07:01:17 UTC
Update Date2020-02-26 21:24:49 UTC
HMDB IDHMDB0003903
Secondary Accession Numbers
  • HMDB03903
Metabolite Identification
Common Name2-Hydroxyethanesulfonate
Description2-Hydroxyethanesulfonate (also known as 2-Hydroxyethanesulfonic acid or isethionic acid) is an organosulfur compound containing a short chain alkane sulfonate linked to a hydroxyl group. It is a water-soluble liquid used in the manufacture of mild, biodegradable, and high-foaming anionic surfactants. These surfactants provide gentle cleansing and a soft skin feel. 2-Hydroxyethanesulfonate forms a colourless, syrupy, and strongly acidic liquid that can form detergents with oleic acid. 2-Hydroxyethanesulfonate is frequently used in the industrial production of taurine. Mammals are also able to endogenously synthesize 2-hydroxyethanesulfonate via taurine through a possible enzymatic deamination process (PMID: 14490797 ). 2-Hydroxyethanesulfonate can be found in both human plasma and urine (PMID: 1159536 , PMID: 6066118 ). Higher plasma levels of 2-hydroxyethanesulfonate have been shown to be protective against type 2 diabetes.
Structure
Data?1582752289
Synonyms
ValueSource
2-Hydroxyethane-1-sulfonic acidChEBI
2-Hydroxyethanesulfonic acidChEBI
2-Hydroxyethylsulfonic acidChEBI
beta-Hydroxyethanesulfonic acidChEBI
Isethionic acidKegg
IsethionateKegg
2-Hydroxyethane-1-sulfonateGenerator
2-Hydroxyethane-1-sulphonateGenerator
2-Hydroxyethane-1-sulphonic acidGenerator
2-HydroxyethanesulphonateGenerator
2-Hydroxyethanesulphonic acidGenerator
2-HydroxyethylsulfonateGenerator
2-HydroxyethylsulphonateGenerator
2-Hydroxyethylsulphonic acidGenerator
b-HydroxyethanesulfonateGenerator
b-Hydroxyethanesulfonic acidGenerator
b-HydroxyethanesulphonateGenerator
b-Hydroxyethanesulphonic acidGenerator
beta-HydroxyethanesulfonateGenerator
beta-HydroxyethanesulphonateGenerator
beta-Hydroxyethanesulphonic acidGenerator
Β-hydroxyethanesulfonateGenerator
Β-hydroxyethanesulfonic acidGenerator
Β-hydroxyethanesulphonateGenerator
Β-hydroxyethanesulphonic acidGenerator
(2-Hydroxyethyl)sulfonateHMDB
(2-Hydroxyethyl)sulfonic acidHMDB
EthanolsulfonateHMDB
Ethanolsulfonic acidHMDB
HydroxyethylsulfonateHMDB
Hydroxyethylsulfonic acidHMDB, MeSH
Isethionic acid sodium saltHMDB
Kyselina isethionovaHMDB
Potassium 2-hydroxyethanesulfonateHMDB
Potassium isethionateHMDB
Sodium 2-hydroxyethanesulfonateHMDB
Sodium 2-hydroxyethyl sulfonateHMDB
Sodium beta-hydroxyethanesulfonateHMDB
Sodium isethionateHMDB, MeSH
Isethionate, sodiumMeSH, HMDB
Acid, isethionicMeSH, HMDB
Isethionic acid monopotassium saltMeSH, HMDB
Isethionic acid monosodium saltMeSH, HMDB
Acid, hydroxyethylsulfonicMeSH, HMDB
Isethionic acid monoammonium saltMeSH, HMDB
2-HydroxyethanesulfonateGenerator
Chemical FormulaC2H6O4S
Average Molecular Weight126.132
Monoisotopic Molecular Weight125.99867937
IUPAC Name2-hydroxyethane-1-sulfonic acid
Traditional Namesodium isethionate
CAS Registry Number107-36-8
SMILES
OCCS(O)(=O)=O
InChI Identifier
InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)
InChI KeySUMDYPCJJOFFON-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acids
Alternative Parents
Substituents
  • Alkanesulfonic acid
  • Sulfonyl
  • Organosulfonic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility103 g/LALOGPS
logP10(-2.2) g/LALOGPS
logP10(-2.9) g/LChemAxon
logS10(-0.09) g/LALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.95 m³·mol⁻¹ChemAxon
Polarizability10.43 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.59131661259
DarkChem[M-H]-115.79331661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxyethanesulfonate,1TMS,#1C[Si](C)(C)OCCS(=O)(=O)O1365.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyethanesulfonate,1TMS,#2C[Si](C)(C)OS(=O)(=O)CCO1332.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyethanesulfonate,1TBDMS,#1CC(C)(C)[Si](C)(C)OCCS(=O)(=O)O1628.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
2-Hydroxyethanesulfonate,1TBDMS,#2CC(C)(C)[Si](C)(C)OS(=O)(=O)CCO1601.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyethanesulfonate GC-MS (Non-derivatized) - 70eV, Positivesplash10-000y-9100000000-91c2f22c70185fb5bafe2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyethanesulfonate GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9300000000-7f0eccc0156cbd7e5b232017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxyethanesulfonate 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 - 2-Hydroxyethanesulfonate LC-ESI-QQ , negative-QTOFsplash10-004i-0900000000-b8df238a554a2725a4d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyethanesulfonate LC-ESI-QQ , negative-QTOFsplash10-004i-6900000000-c72536efb4cfd09b27592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyethanesulfonate LC-ESI-QQ , negative-QTOFsplash10-001i-9000000000-61473ee5b4612e7ca2732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyethanesulfonate LC-ESI-QQ , negative-QTOFsplash10-001i-9000000000-d85e73096201062faad22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyethanesulfonate LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-ce44d57a4275daa8f5632017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 40V, Negative-QTOFsplash10-004i-9000000000-981a5a0ee1738f6dd44b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 20V, Negative-QTOFsplash10-0002-9000000000-2bcca3d457e8f9197dda2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 10V, Negative-QTOFsplash10-0002-9300000000-620379edca41de90b8d32021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 10V, Positive-QTOFsplash10-056r-0900000000-f83dca3bb4164fb39fc22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 20V, Positive-QTOFsplash10-054k-8900000000-111dba10014f3cc5c4032015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 40V, Positive-QTOFsplash10-056r-9300000000-5cc44eb483ce09d495102015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 10V, Negative-QTOFsplash10-00e9-6900000000-c1573e4b7aa0acf670182015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 20V, Negative-QTOFsplash10-0089-9600000000-894c171421adedc823bb2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 40V, Negative-QTOFsplash10-001i-9000000000-b8c542a1a77eb7a6a1912015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 10V, Negative-QTOFsplash10-00di-0900000000-6b3e5cddcb84b830073f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 20V, Negative-QTOFsplash10-001i-9000000000-a6fb8cd4d3dc149be3092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 40V, Negative-QTOFsplash10-001i-9000000000-d1be4ea1280b92cdc8d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 10V, Positive-QTOFsplash10-0059-5900000000-946a0582ff1c22137b292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 20V, Positive-QTOFsplash10-03ea-9200000000-1efad064df378bad76b12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxyethanesulfonate 40V, Positive-QTOFsplash10-03di-9000000000-2c4a3db8921d94d7f5262021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDFDB023245
KNApSAcK IDNot Available
Chemspider ID7578
KEGG Compound IDC05123
BioCyc IDCPD-3745
BiGG IDNot Available
Wikipedia LinkIsethionic_acid
METLIN ID6987
PubChem Compound7866
PDB IDNot Available
ChEBI ID1157
Food Biomarker OntologyNot Available
VMH IDISETAC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChen, Zhiwen; Liao, Xiangxu; Qian, Weiqiang; et al. Process for preparation of hydroxyalkanesulfonic acids for plating solutions. Faming Zhuanli Shenqing Gongkai Shuomingshu (1990), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kersten A, Althaus C, Seitz HM, Pfahl HG, Sundmacher R: [Bilateral microsporidial keratitis in an HIV-positive patient with AIDS stage infection]. Klin Monbl Augenheilkd. 1998 Jun;212(6):476-9. [PubMed:9715470 ]
  2. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
  3. READ WO, WELTY JD: Synthesis of taurine and isethionic acid by dog heart slices. J Biol Chem. 1962 May;237:1521-2. [PubMed:14490797 ]
  4. Sturman JA, Hepner GW, Hofmann AF, Thomas PJ: Metabolism of [35S]taurine in man. J Nutr. 1975 Sep;105(9):1206-14. [PubMed:1159536 ]
  5. Jacobsen JG, Collins LL, Smith LH Jr: Urinary excretion of isethionic acid in man. Nature. 1967 Jun 17;214(5094):1247-8. [PubMed:6066118 ]