Showing metabocard for Isethionic acid (MMDBc0049987)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 22:47:40 UTC
Update Date2022-12-15 22:52:20 UTC
Metabolite IDMMDBc0049987
Metabolite Identification
Common NameIsethionic acid
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fed14552090>

      
  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 #<Metabolite:0x00007fed14552090>

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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3D SDF for #<Metabolite:0x00007fed14552090>

      
  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>
MMDBc0049987

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fed14552090>

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 #<Metabolite:0x00007fed14552090>

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 #<Metabolite:0x00007fed14552090>

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 #<Metabolite:0x00007fed14552090>

OCCS(O)(=O)=O
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INCHI for #<Metabolite:0x00007fed14552090>

InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)
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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
Molecular FormulaC2H6O4S
Average Mass126.132
Monoisotopic Mass125.99867937
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