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Showing NP-Card for Isethionic acid (NP0002659)

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Record Information
Version1.0
Created at2020-11-23 18:26:16 UTC
Updated at2021-08-12 19:51:47 UTC
NP-MRD IDNP0002659
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsethionic acid
Provided ByBMRBBMRB logo
Description2-Hydroxyethanesulfonate, also known as isethionic acid or isethionate, 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). 2-Hydroxyethanesulfonate exists in all living organisms, ranging from bacteria to humans. 2-Hydroxyethanesulfonate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Isethionic acid is found in Tichocarpus crinitus and Trypanosoma brucei. It was first documented in 1962 (PMID: 14490797). Based on a literature review a small amount of articles have been published on 2-Hydroxyethanesulfonate (PMID: 17984079) (PMID: 9715470) (PMID: 21389975) (PMID: 1159536).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002659 (Isethionic acid)


     RDKit          2D

 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.5000    1.6999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.1999    0.0000 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.5000   -1.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.1999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000    0.1999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500   -1.0992    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -1.3001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    1.6999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -1.0992    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  1
  2  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  5  9  1  1
  5 10  1  0
  6 11  1  1
  6 12  1  0
  7 13  1  0
M  END
Download

3D MOL for NP0002659 (Isethionic acid)

NP0002659
     RDKit          3D

 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.9769    0.1049    1.8122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3593   -0.3751    0.5296 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.4968   -1.8793    0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1822    0.3071   -0.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462    0.0694    0.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809   -0.3616   -0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4111    0.0352   -0.5632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -0.3740   -1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640    1.1511    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103   -0.4439    1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0970   -1.4777   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686    0.0256   -1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9628   -0.6463   -0.1246 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 NP0002659 (Isethionic acid)


     RDKit          2D

 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.5000    1.6999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.1999    0.0000 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.5000   -1.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.1999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000    0.1999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500   -1.0992    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -1.3001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    1.6999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -1.0992    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  1
  2  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  5  9  1  1
  5 10  1  0
  6 11  1  1
  6 12  1  0
  7 13  1  0
M  END
> <DATABASE_ID>
NP0002659

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0002659 (Isethionic acid)

NP0002659
     RDKit          3D

 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.9769    0.1049    1.8122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3593   -0.3751    0.5296 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.4968   -1.8793    0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1822    0.3071   -0.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462    0.0694    0.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809   -0.3616   -0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4111    0.0352   -0.5632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8258   -0.3740   -1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4640    1.1511    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103   -0.4439    1.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0970   -1.4777   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686    0.0256   -1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9628   -0.6463   -0.1246 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

PDB for NP0002659 (Isethionic acid)

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 NP0002659 (Isethionic acid)

COMPND    NP0002659
HETATM    1  O1  UNL     1      -1.977   0.105   1.812  1.00  0.00           O  
HETATM    2  S1  UNL     1      -1.359  -0.375   0.530  1.00  0.00           S  
HETATM    3  O2  UNL     1      -1.497  -1.879   0.522  1.00  0.00           O  
HETATM    4  O3  UNL     1      -2.182   0.307  -0.755  1.00  0.00           O  
HETATM    5  C1  UNL     1       0.346   0.069   0.555  1.00  0.00           C  
HETATM    6  C2  UNL     1       1.081  -0.362  -0.684  1.00  0.00           C  
HETATM    7  O4  UNL     1       2.411   0.035  -0.563  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.826  -0.374  -1.076  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.464   1.151   0.717  1.00  0.00           H  
HETATM   10  H3  UNL     1       0.810  -0.444   1.421  1.00  0.00           H  
HETATM   11  H4  UNL     1       1.097  -1.478  -0.744  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.669   0.026  -1.610  1.00  0.00           H  
HETATM   13  H6  UNL     1       2.963  -0.646  -0.125  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 NP0002659 (Isethionic acid)

OCCS(O)(=O)=O
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INCHI for NP0002659 (Isethionic acid)

InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)
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View in JSmol
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 Mass126.1320 Da
Monoisotopic Mass125.99868 Da
IUPAC Name2-hydroxyethane-1-sulfonic acid
Traditional Namesodium isethionate
CAS Registry NumberNot Available
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tichocarpus crinitusLOTUS Database
Trypanosoma bruceiLOTUS Database
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot 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-2.2ALOGPS
logP-2.9ChemAxon
logS-0.09ALOGPS
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
HMDB IDHMDB0003903
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. 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. doi: 10.1055/s-2008-1034934. [PubMed:9715470 ]
  3. 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 ]
  4. READ WO, WELTY JD: Synthesis of taurine and isethionic acid by dog heart slices. J Biol Chem. 1962 May;237:1521-2. [PubMed:14490797 ]
  5. Sturman JA, Hepner GW, Hofmann AF, Thomas PJ: Metabolism of [35S]taurine in man. J Nutr. 1975 Sep;105(9):1206-14. doi: 10.1093/jn/105.9.1206. [PubMed:1159536 ]