Showing metabocard for toluene-4-sulfonic acid (MMDBc0054677)

Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 23:23:55 UTC
Update Date2025-10-07 16:08:37 UTC
Metabolite IDMMDBc0054677
Metabolite Identification
Common Nametoluene-4-sulfonic acid
DescriptionToluene-4-sulfonic acid is a sulfonic acid and a key chemical reagent widely utilized in organic synthesis and polymer chemistry. Its chemical structure features a toluene ring substituted with a sulfonic acid group at the para position, making it a strong acid and effective catalyst in various reactions. In the synthesis of polyaniline-Zn/V2O5 nanocomposites, toluene-4-sulfonic acid monohydrate serves as an anionic surfactant, facilitating in situ oxidation polymerization (PMID:39139231 ). Additionally, it acts as a catalyst in the Kabachnik-Fields reaction to produce phosphorylated chitosan, highlighting its role in creating complex materials (PMID:35160409 ). The compound is also involved in the development of fluorescent labeling reagents for sensitive detection of free fatty acids in ginkgo samples, showcasing its versatility in analytical chemistry (PMID:35541139 ). Moreover, toluene-4-sulfonic acid has been identified as a potent inhibitor in biochemical pathways, demonstrating its potential in medicinal chemistry (PMID:20675132 ). Its applications extend to rearrangements in organic reactions, where it contributes to the formation of various derivatives under mild conditions (PMID:21202930 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9a9ddf9e38>


  Mrv1533004251515342D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
M  CHG  1  11  -1
M  END
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3D MOL for #<Metabolite:0x00007f9a9ddf9e38>

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3D SDF for #<Metabolite:0x00007f9a9ddf9e38>

  Mrv1533004251515342D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
M  CHG  1  11  -1
M  END
> <DATABASE_ID>
MMDBc0054677

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=CC=C(C=C1)S([O-])(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10)/p-1

> <INCHI_KEY>
JOXIMZWYDAKGHI-UHFFFAOYSA-M

> <FORMULA>
C7H7O3S

> <MOLECULAR_WEIGHT>
171.19

> <EXACT_MASS>
171.012138839

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
16.08814225855698

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methylbenzene-1-sulfonate

> <ALOGPS_LOGP>
0.96

> <JCHEM_LOGP>
1.6675739219999997

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.1372879562372242

> <JCHEM_POLAR_SURFACE_AREA>
57.2

> <JCHEM_REFRACTIVITY>
40.6

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tosylate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9a9ddf9e38>
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PDB for #<Metabolite:0x00007f9a9ddf9e38>
HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.206  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for #<Metabolite:0x00007f9a9ddf9e38>
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SMILES for #<Metabolite:0x00007f9a9ddf9e38>
CC1=CC=C(C=C1)S([O-])(=O)=O
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INCHI for #<Metabolite:0x00007f9a9ddf9e38>
InChI=1S/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10)/p-1
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Synonyms
ValueSource
4-Methylbenzenesulfonic acid, ion(1-)ChEBI
4-Toluene sulfonateChEBI
4-ToluenesulfonateChEBI
p-Toluene sulfonateChEBI
p-ToluenesulfonateChEBI
TosylateChEBI
4-Methylbenzenesulfonate, ion(1-)Generator
4-Methylbenzenesulphonate, ion(1-)Generator
4-Methylbenzenesulphonic acid, ion(1-)Generator
4-Toluene sulfonic acidGenerator
4-Toluene sulphonateGenerator
4-Toluene sulphonic acidGenerator
4-Toluenesulfonic acidGenerator
4-ToluenesulphonateGenerator
4-Toluenesulphonic acidGenerator
p-Toluene sulfonic acidGenerator
p-Toluene sulphonateGenerator
p-Toluene sulphonic acidGenerator
p-Toluenesulfonic acidGenerator
p-ToluenesulphonateGenerator
p-Toluenesulphonic acidGenerator
Tosylic acidGenerator
Toluene-4-sulfonic acidGenerator
Toluene-4-sulphonateGenerator
Toluene-4-sulphonic acidGenerator
4-Methylbenzene-1-sulfonic acidGenerator
4-Methylbenzene-1-sulphonateGenerator
4-Methylbenzene-1-sulphonic acidGenerator
Molecular FormulaC7H7O3S
Average Mass171.19
Monoisotopic Mass171.012138839
IUPAC Name4-methylbenzene-1-sulfonate
Traditional Nametosylate
CAS Registry NumberNot Available
SMILES
CC1=CC=C(C=C1)S([O-])(=O)=O
InChI Identifier
InChI=1S/C7H8O3S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H,8,9,10)/p-1
InChI KeyJOXIMZWYDAKGHI-UHFFFAOYSA-M