Showing metabocard for p-Cresol sulfate (MMDBc0000002)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:38:04 UTC
Update Date2024-04-30 19:32:27 UTC
Metabolite IDMMDBc0000002
Metabolite Identification
Common Namep-Cresol sulfate
Descriptionp-Cresol sulfate is a microbial metabolite that is found in urine and likely derives from secondary metabolism of p-cresol. It appears to be elevated in the urine of individuals with progressive multiple sclerosis (PMID:10775436 ). p-Cresol sulfate is the major component of urinary MBPLM (myelin basic protein-like material). p-Cresol sulfate is a small protein-bound molecule that is poorly cleared with dialysis. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821 ). Uremic toxins include other low-molecular-weight compounds such as indoxyl sulfate, 3-carboxy-4-methyl-5-propyl-2-furanpropionic acid, and asymmetric dimethylarginine (PMID:18941347 ). It has also been linked to cardiovascular disease and oxidative injury. Higher levels are associated with overgrowth of intestinal bacteria from Clostridia species, including C. difficile. p-Cresol is generated by the partial breakdown of tyrosine and phenylalanine by a wide range of intestinal obligate or facultative anaerobes, including the genera Bacteroides, Lactobacillus, Enterobacter, Bifidobacterium, and especially Clostridium (PMID:2394806 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f923c768380>


  Mrv1652305271900252D          

 12 12  0  0  0  0            999 V2000
10001.763710001.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.048510000.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.334110001.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.619510000.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6195 9999.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3340 9999.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0485 9999.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4679 9999.5367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1862 9999.9526    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9998.597910000.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.772410000.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9031 9999.5367    0.0000 O   0  0  0  0  0  0  0  0  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
  7  2  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
  9  8  1  0  0  0  0
 12  5  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f923c768380>

HMDB0011635
     RDKit          3D
p-Cresol sulfate
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.3231    0.3918   -0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8924    0.0648    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0728    1.0067    0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    0.8065    0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8073   -0.4300    0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455   -0.7440    0.7888 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2493   -0.3960   -0.4544 S   0  0  0  0  0  6  0  0  0  0  0  0
    4.6665   -0.5662    0.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0043   -1.2579   -1.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0325    1.2075   -0.9311 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0046   -1.4065    0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3324   -1.1513   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7940    0.4928    0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8546   -0.4069   -0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4242    1.3748   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592    1.9892    0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9101    1.5643    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5996    1.7568   -0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366   -2.3810   -0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9752   -1.9155   -0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  5 11  1  0
 11 12  2  0
 12  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  4 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f923c768380>


  Mrv1652305271900252D          

 12 12  0  0  0  0            999 V2000
10001.763710001.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.048510000.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.334110001.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.619510000.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6195 9999.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3340 9999.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0485 9999.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4679 9999.5367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1862 9999.9526    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9998.597910000.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.772410000.6675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9031 9999.5367    0.0000 O   0  0  0  0  0  0  0  0  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
  7  2  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
  9  8  1  0  0  0  0
 12  5  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000002

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=CC=C(OS(O)(=O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O4S/c1-6-2-4-7(5-3-6)11-12(8,9)10/h2-5H,1H3,(H,8,9,10)

> <INCHI_KEY>
WGNAKZGUSRVWRH-UHFFFAOYSA-N

> <FORMULA>
C7H8O4S

> <MOLECULAR_WEIGHT>
188.201

> <EXACT_MASS>
188.014329434

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
17.167826547239486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4-methylphenyl)oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.55

> <JCHEM_LOGP>
1.7077885373333332

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.0403797360664067

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
43.0719

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4-methylphenyl)oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f923c768380>

HMDB0011635
     RDKit          3D
p-Cresol sulfate
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.3231    0.3918   -0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8924    0.0648    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0728    1.0067    0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    0.8065    0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8073   -0.4300    0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455   -0.7440    0.7888 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2493   -0.3960   -0.4544 S   0  0  0  0  0  6  0  0  0  0  0  0
    4.6665   -0.5662    0.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0043   -1.2579   -1.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0325    1.2075   -0.9311 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0046   -1.4065    0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3324   -1.1513   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7940    0.4928    0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8546   -0.4069   -0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4242    1.3748   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592    1.9892    0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9101    1.5643    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5996    1.7568   -0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366   -2.3810   -0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9752   -1.9155   -0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  5 11  1  0
 11 12  2  0
 12  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  4 17  1  0
 10 18  1  0
 11 19  1  0
 12 20  1  0
M  END
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PDB for #<Metabolite:0x00007f923c768380>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8669.9598668.884   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.6248668.114   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.2908668.884   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.9568668.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8665.9568666.574   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8667.2908665.804   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8668.6248666.574   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8661.9408665.802   0.000  0.00  0.00           O+0
HETATM    9  S   UNK     0    8663.2818666.578   0.000  0.00  0.00           S+0
HETATM   10  O   UNK     0    8664.0498667.913   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8662.5088667.913   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8664.6198665.802   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    3    7    1                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    9                                                            
CONECT    9   10   11   12    8                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9    5                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for #<Metabolite:0x00007f923c768380>

COMPND    HMDB0011635
HETATM    1  C1  UNL     1      -3.323   0.392  -0.104  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.892   0.065   0.118  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.073   1.007   0.684  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.272   0.807   0.934  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.807  -0.430   0.584  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.145  -0.744   0.789  1.00  0.00           O  
HETATM    7  S1  UNL     1       3.249  -0.396  -0.454  1.00  0.00           S  
HETATM    8  O2  UNL     1       4.666  -0.566   0.051  1.00  0.00           O  
HETATM    9  O3  UNL     1       3.004  -1.258  -1.674  1.00  0.00           O  
HETATM   10  O4  UNL     1       3.033   1.208  -0.931  1.00  0.00           O  
HETATM   11  C6  UNL     1       0.005  -1.406   0.009  1.00  0.00           C  
HETATM   12  C7  UNL     1      -1.332  -1.151  -0.218  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.794   0.493   0.910  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.855  -0.407  -0.641  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.424   1.375  -0.605  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.459   1.989   0.971  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.910   1.564   1.384  1.00  0.00           H  
HETATM   18  H6  UNL     1       3.600   1.757  -0.304  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.437  -2.381  -0.264  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.975  -1.916  -0.672  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3   12
CONECT    3    4   16
CONECT    4    5    5   17
CONECT    5    6   11
CONECT    6    7
CONECT    7    8    8    9    9
CONECT    7   10
CONECT   10   18
CONECT   11   12   12   19
CONECT   12   20
END
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SMILES for #<Metabolite:0x00007f923c768380>

CC1=CC=C(OS(O)(=O)=O)C=C1
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INCHI for #<Metabolite:0x00007f923c768380>

InChI=1S/C7H8O4S/c1-6-2-4-7(5-3-6)11-12(8,9)10/h2-5H,1H3,(H,8,9,10)
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Synonyms
ValueSource
4-Cresol sulfateChEBI
Sulfuric acid mono-p-tolyl esterChEBI
4-Cresol sulfuric acidGenerator
4-Cresol sulphateGenerator
4-Cresol sulphuric acidGenerator
Sulfate mono-p-tolyl esterGenerator
Sulphate mono-p-tolyl esterGenerator
Sulphuric acid mono-p-tolyl esterGenerator
p-Cresol sulfuric acidGenerator
p-Cresol sulphateGenerator
p-Cresol sulphuric acidGenerator
mono(4-Methylphenyl) sulfateHMDB
p-Cresyl sulfateHMDB
p-Cresyl sulphateHMDB
p-Cresyl-sulfateHMDB
p-Cresyl-sulphateHMDB
p-CresylsulfateHMDB
p-CresylsulphateHMDB
p-Tolyl sulfate (6ci,7ci)HMDB
p-Tolyl sulphate (6ci,7ci)HMDB
Para-cresol sulfateHMDB
Para-cresol sulphateHMDB
Sulfuric acid mono(p-tolyl) ester (8ci)HMDB
Sulfuric acid, mono(4-methylphenyl) esterHMDB
Molecular FormulaC7H8O4S
Average Mass188.201
Monoisotopic Mass188.014329434
IUPAC Name(4-methylphenyl)oxidanesulfonic acid
Traditional Name(4-methylphenyl)oxidanesulfonic acid
CAS Registry NumberNot Available
SMILES
CC1=CC=C(OS(O)(=O)=O)C=C1
InChI Identifier
InChI=1S/C7H8O4S/c1-6-2-4-7(5-3-6)11-12(8,9)10/h2-5H,1H3,(H,8,9,10)
InChI KeyWGNAKZGUSRVWRH-UHFFFAOYSA-N