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Showing NP-Card for p-Cresol sulfate (NP0001479)

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Record Information
Version1.0
Created at2009-01-30 15:08:14 UTC
Updated at2021-06-30 02:06:20 UTC
NP-MRD IDNP0001479
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001479 (p-Cresol sulfate)


  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 NP0001479 (p-Cresol sulfate)

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 NP0001479 (p-Cresol sulfate)


  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>
NP0001479

> <DATABASE_NAME>
NP-MRD

> <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 NP0001479 (p-Cresol sulfate)

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

PDB for NP0001479 (p-Cresol sulfate)

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 NP0001479 (p-Cresol sulfate)

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 NP0001479 (p-Cresol sulfate)

CC1=CC=C(OS(O)(=O)=O)C=C1
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INCHI for NP0001479 (p-Cresol sulfate)

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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View in JSmol
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
Chemical FormulaC7H8O4S
Average Mass188.2010 Da
Monoisotopic Mass188.01433 Da
IUPAC Name(4-methylphenyl)oxidanesulfonic acid
Traditional Name(4-methylphenyl)oxidanesulfonic acid
CAS Registry Number3233-58-7
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)V.dorna832021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-13View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)V.dorna832021-08-13View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-13View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-13View Spectrum
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
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassArylsulfates
Direct ParentPhenylsulfates
Alternative Parents
Substituents
  • Phenylsulfate
  • Phenoxy compound
  • Toluene
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Sulfuric acid monoester
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP-0.55ALOGPS
logP1.71ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.07 m³·mol⁻¹ChemAxon
Polarizability17.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011635
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028333
KNApSAcK IDC00052378
Chemspider ID3806481
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4615423
PDB IDNot Available
ChEBI ID82914
Good Scents IDNot Available
References
General References
  1. Cao L, Kirk MC, Coward LU, Jackson P, Whitaker JN: p-Cresol sulfate is the dominant component of urinary myelin basic protein like material. Arch Biochem Biophys. 2000 May 1;377(1):9-21. [PubMed:10775436 ]
  2. Raff AC, Meyer TW, Hostetter TH: New insights into uremic toxicity. Curr Opin Nephrol Hypertens. 2008 Nov;17(6):560-5. doi: 10.1097/MNH.0b013e32830f45b6. [PubMed:18941347 ]
  3. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  4. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  5. Sivsammye G, Sims HV: Presumptive identification of Clostridium difficile by detection of p-cresol in prepared peptone yeast glucose broth supplemented with p-hydroxyphenylacetic acid. J Clin Microbiol. 1990 Aug;28(8):1851-3. doi: 10.1128/jcm.28.8.1851-1853.1990. [PubMed:2394806 ]