Showing metabocard for isethionate (MMDBc0032175)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-18 02:05:34 UTC
Update Date2025-11-05 17:13:04 UTC
Metabolite IDMMDBc0032175
Metabolite Identification
Common Name isethionate
DescriptionIsethionate is a sulfonate compound belonging to the class of metabolites. Its chemical structure features a two-carbon chain (ethanol) linked to a sulfonate group, making it a unique C2-sulfonate. Isethionate is involved in various biochemical pathways, including its role in microbial metabolism, where specific anaerobic bacteria, such as Wadsworthia, can utilize isethionate to produce hydrogen sulfide (H2S), acetate, and ethanol (PMID:40447622 ). Additionally, isethionate is present in formulations like sodium cocoyl isethionate, which is used in coacervate preparations with other surfactants (PMID:40905482 ). In clinical contexts, isethionate derivatives, such as propamidine isethionate, are utilized in therapeutic applications, including eye drops with low bioavailability (PMID:40461627 ) and in combination therapies with antifungal agents (PMID:40135873 ). Furthermore, studies have indicated that isethionate levels are significantly altered in certain medical conditions, such as MOGAD, where patients exhibit lower concentrations compared to healthy individuals (PMID:40978201 ). Overall, isethionate serves as an important metabolite in both microbial and therapeutic contexts.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9af04b5ea0>


  Mrv1533004241507062D          

  7  6  0  0  0  0            999 V2000
    0.1105   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
M  CHG  1   7  -1
M  END
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3D MOL for #<Metabolite:0x00007f9af04b5ea0>

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3D SDF for #<Metabolite:0x00007f9af04b5ea0>

  Mrv1533004241507062D          

  7  6  0  0  0  0            999 V2000
    0.1105   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
M  CHG  1   7  -1
M  END
> <DATABASE_ID>
MMDBc0032175

> <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)/p-1

> <INCHI_KEY>
SUMDYPCJJOFFON-UHFFFAOYSA-M

> <FORMULA>
C2H5O4S

> <MOLECULAR_WEIGHT>
125.12

> <EXACT_MASS>
124.991403395

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
10.03495861042974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxyethane-1-sulfonate

> <ALOGPS_LOGP>
-1.19

> <JCHEM_LOGP>
-2.909391904223454

> <ALOGPS_LOGS>
0.01

> <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>
77.42999999999999

> <JCHEM_REFRACTIVITY>
21.825900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isethionate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9af04b5ea0>
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PDB for #<Metabolite:0x00007f9af04b5ea0>
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       0.206  -3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.206  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       1.540   0.000   0.000  0.00  0.00           S+0
HETATM    5  O   UNK     0       1.540   1.540   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.080  -0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for #<Metabolite:0x00007f9af04b5ea0>
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SMILES for #<Metabolite:0x00007f9af04b5ea0>
OCCS([O-])(=O)=O
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INCHI for #<Metabolite:0x00007f9af04b5ea0>
InChI=1S/C2H6O4S/c3-1-2-7(4,5)6/h3H,1-2H2,(H,4,5,6)/p-1
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Synonyms
ValueSource
2-Hydroxyethane-1-sulfonateChEBI
2-Hydroxyethanesulfonate(1-)ChEBI
Isethionate(1-)ChEBI
2-Hydroxyethane-1-sulfonic acidGenerator
2-Hydroxyethane-1-sulphonateGenerator
2-Hydroxyethane-1-sulphonic acidGenerator
2-Hydroxyethanesulfonic acid(1-)Generator
2-Hydroxyethanesulphonate(1-)Generator
2-Hydroxyethanesulphonic acid(1-)Generator
Isethionic acid(1-)Generator
Isethionic acidGenerator
Molecular FormulaC2H5O4S
Average Mass125.12
Monoisotopic Mass124.991403395
IUPAC Name2-hydroxyethane-1-sulfonate
Traditional Nameisethionate
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)/p-1
InChI KeySUMDYPCJJOFFON-UHFFFAOYSA-M