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Showing metabocard for 2-Hydroxyethanesulfonate (HMDB0003903)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 07:01:17 UTC
Update Date2023-02-21 17:16:50 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003903 (2-Hydroxyethanesulfonate)

      
  Mrv1652312111717162D          

  7  6  0  0  0  0            999 V2000
   25.0343   -8.8817    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.3198   -9.2942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1777   -8.4692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6218   -8.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4468   -9.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7488   -8.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4633   -8.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
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3D MOL for HMDB0003903 (2-Hydroxyethanesulfonate)

HMDB0003903
     RDKit          3D
2-Hydroxyethanesulfonate
 13 12  0  0  0  0  0  0  0  0999 V2000
    0.4514    1.5087    1.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0061    0.8367   -0.0748 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.8325    1.6967   -1.3098 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6274    0.5043    0.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1670   -0.7017   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3077   -0.4927   -0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5439    0.2841   -1.7213 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7134   -0.3723    0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524   -1.3386    0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597   -1.2471   -1.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7407   -0.0100    0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7651   -1.4936   -0.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    0.8255   -1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  5  9  1  0
  5 10  1  0
  6 11  1  0
  6 12  1  0
  7 13  1  0
M  END
Download

3D SDF for HMDB0003903 (2-Hydroxyethanesulfonate)

      
  Mrv1652312111717162D          

  7  6  0  0  0  0            999 V2000
   25.0343   -8.8817    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.3198   -9.2942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1777   -8.4692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6218   -8.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4468   -9.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7488   -8.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4633   -8.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003903

> <DATABASE_NAME>
hmdb

> <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_KEY>
SUMDYPCJJOFFON-UHFFFAOYSA-N

> <FORMULA>
C2H6O4S

> <MOLECULAR_WEIGHT>
126.132

> <EXACT_MASS>
125.99867937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
10.432092149920027

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxyethane-1-sulfonic acid

> <ALOGPS_LOGP>
-2.17

> <JCHEM_LOGP>
-2.909391904223454

> <ALOGPS_LOGS>
-0.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.11989502666312

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.443707513577011

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8786483116308847

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
22.947599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sodium isethionate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0003903 (2-Hydroxyethanesulfonate)

HMDB0003903
     RDKit          3D
2-Hydroxyethanesulfonate
 13 12  0  0  0  0  0  0  0  0999 V2000
    0.4514    1.5087    1.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0061    0.8367   -0.0748 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.8325    1.6967   -1.3098 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6274    0.5043    0.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1670   -0.7017   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3077   -0.4927   -0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5439    0.2841   -1.7213 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7134   -0.3723    0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524   -1.3386    0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597   -1.2471   -1.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7407   -0.0100    0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7651   -1.4936   -0.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    0.8255   -1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  5  9  1  0
  5 10  1  0
  6 11  1  0
  6 12  1  0
  7 13  1  0
M  END
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PDB for HMDB0003903 (2-Hydroxyethanesulfonate)

HEADER    PROTEIN                                 11-DEC-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-DEC-17         0                                  
HETATM    1  S   UNK     0      46.731 -16.579   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      45.397 -17.349   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      50.732 -15.809   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      45.961 -15.245   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      47.501 -17.913   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      48.064 -15.809   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      49.398 -16.579   0.000  0.00  0.00           C+0
CONECT    1    2    4    5    6                                             
CONECT    2    1                                                            
CONECT    3    7                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    1    7                                                       
CONECT    7    3    6                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0003903 (2-Hydroxyethanesulfonate)

COMPND    HMDB0003903
HETATM    1  O1  UNL     1       0.451   1.509   1.140  1.00  0.00           O  
HETATM    2  S1  UNL     1       1.006   0.837  -0.075  1.00  0.00           S  
HETATM    3  O2  UNL     1       0.833   1.697  -1.310  1.00  0.00           O  
HETATM    4  O3  UNL     1       2.627   0.504   0.210  1.00  0.00           O  
HETATM    5  C1  UNL     1       0.167  -0.702  -0.340  1.00  0.00           C  
HETATM    6  C2  UNL     1      -1.308  -0.493  -0.606  1.00  0.00           C  
HETATM    7  O4  UNL     1      -1.544   0.284  -1.721  1.00  0.00           O  
HETATM    8  H1  UNL     1       2.713  -0.372   0.679  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.252  -1.339   0.564  1.00  0.00           H  
HETATM   10  H3  UNL     1       0.660  -1.247  -1.169  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.741  -0.010   0.289  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.765  -1.494  -0.735  1.00  0.00           H  
HETATM   13  H6  UNL     1      -2.353   0.826  -1.535  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4    5
CONECT    4    8
CONECT    5    6    9   10
CONECT    6    7   11   12
CONECT    7   13
END
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SMILES for HMDB0003903 (2-Hydroxyethanesulfonate)

OCCS(O)(=O)=O
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INCHI for HMDB0003903 (2-Hydroxyethanesulfonate)

InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
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 Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
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)Not Available
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 ]