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Showing NP-Card for p-Cresol (NP0001009)

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Record Information
Version1.0
Created at2006-02-22 10:50:16 UTC
Updated at2021-10-07 20:40:23 UTC
NP-MRD IDNP0001009
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Cresol
DescriptionPara-Cresol, also 4-methylphenol, is an organic compound with the formula CH3C6H4(OH). P-cresol is a cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals. It has a role as a uremic toxin, a human metabolite and an Escherichia coli metabolite. It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of o-cresol and m-cresol. It is a partially lipophilic moiety which strongly binds to plasma protein (close to 100%) under normal conditions. P-Cresol is metabolized through conjugation, mainly sulphation and glucuronization, but removal of the unconjugated p-cresol is, at least in part, via the urine. Therefore it is not surprising that this compound, together with several other phenoles, is retained when the kidneys fail. P-Cresol is an end-product of protein breakdown, and an increase of the nutritional protein load in healthy individuals results in enhanced generation and urinary excretion. The serum p-cresol concentration in uremic patients can be decreased by changing to a low-protein diet. P-Cresol is one of the metabolites of the amino acid tyrosine, and to a certain extent also of phenylalanine, which are converted to 4-hydroxyphenylacetic acid by intestinal bacteria, before being decarboxylated to p-cresol (putrefaction). The main contributing bacteria are aerobes (mainly enterobacteria), but to a certain extent also anaerobes play a role (mainly Clostridium perfringens). In uremia, modifications in the intestinal flora result in the specific overgrowth of bacteria that are specific p-cresol producers. The administration of antibiotics reduces urinary excretion of p-cresol, as a result of the liquidation of the producing bacteria. Environmental factors might also contribute. The liver cytochrome P450 metabolizes toluene to benzyl alcohol, but also to o-cresol and p-cresol. Toluene is not only used industrially, but it is also the most widely abusively inhaled solvent. Furthermore, p-cresol is a metabolite of menthofuran, one of the metabolites of R-(+)-pulegone, which is found in extracts from the plants Mentha pulegium and Hedeoma pulegioides, commonly known as pennyroyal oil and pennyroyal tea. These extracts are popular as unconventional herbal therapeutic agents and are applied as abortiva, diaphoretics, emmenagogues, and psychedelic drugs. Pennyroyal oil is extensively used for its pleasant mint-like smell in the flavoring industry. The toxicity of pennyroyal oil and menthofuran is well known. Another compound used in traditional medicine, especially in Japan, which is a precursor of p-cresol is wood tar creosote. P-Cresol has been reported to affect several biochemical, biological and physiological functions: (I) it diminishes the oxygen uptake of rat cerebral cortex slices; (ii) it increases the free active drug concentration of warfarin and diazepam; (iii) it has been related to growth retardation in the weanling pig; (iv) it alters cell membrane permeability, at least in bacteria; (v) it induces LDH leakage from rat liver slices; (vi) it induces susceptibility to auditive epileptic crises; and (vii) it blocks cell K+ channels. (PMID: 10570076 ). P-Cresol is a uremic toxin that is at least partially removed by peritoneal dialysis in haemodialysis patients, and has been involved in the progression of renal failure (PMID: 11169029 ). At concentrations encountered during uremia, p-cresol inhibits phagocyte function and decreases leukocyte adhesion to cytokine-stimulated endothelial cells. (PMID: 14681860 ). P-Cresol can be found in Bacteroides, Bifidobacterium, Clostridium, Enterobacter and Lactobacillus (PMID: 2394806 ; PMID: 30208103 ). As a volatile organic compound, it has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001009 (p-Cresol)


  Mrv1652309272007362D          

  8  8  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482    0.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  0  0  0  0
M  END
Download

3D MOL for NP0001009 (p-Cresol)

HMDB0001858
     RDKit          3D
p-Cresol
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.4917    0.0122   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9960   -0.0026   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -1.1791   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1004   -1.1644   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225    0.0083   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2196    0.0251    0.0037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871    1.1759    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912    1.1789    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8257   -0.8254   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7842    1.0063   -0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746   -0.1906    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8275   -2.1089   -0.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6608   -2.0960   -0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6584   -0.0457    0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6601    2.0913    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383    2.1146    0.0989 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
  5  7  1  0
  7  8  2  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
M  END
Download

3D SDF for NP0001009 (p-Cresol)


  Mrv1652309272007362D          

  8  8  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482    0.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001009

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3

> <INCHI_KEY>
IWDCLRJOBJJRNH-UHFFFAOYSA-N

> <FORMULA>
C7H8O

> <MOLECULAR_WEIGHT>
108.1378

> <EXACT_MASS>
108.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.926991180769898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methylphenol

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
2.1831018836666667

> <ALOGPS_LOGS>
-0.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.357335371423924

> <JCHEM_PKA_STRONGEST_BASIC>
-5.436049745016864

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
33.0801

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
P-cresol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001009 (p-Cresol)

HMDB0001858
     RDKit          3D
p-Cresol
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.4917    0.0122   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9960   -0.0026   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -1.1791   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1004   -1.1644   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225    0.0083   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2196    0.0251    0.0037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871    1.1759    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912    1.1789    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8257   -0.8254   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7842    1.0063   -0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746   -0.1906    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8275   -2.1089   -0.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6608   -2.0960   -0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6584   -0.0457    0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6601    2.0913    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383    2.1146    0.0989 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
  5  7  1  0
  7  8  2  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
M  END
Download

PDB for NP0001009 (p-Cresol)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       1.083   3.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.250   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   1.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.083   0.521   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.417   1.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   2.832   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.750   3.602   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.583   0.522   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    3                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for NP0001009 (p-Cresol)

COMPND    HMDB0001858
HETATM    1  C1  UNL     1       2.492   0.012  -0.107  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.996  -0.003  -0.080  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.280  -1.179  -0.163  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.100  -1.164  -0.135  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.823   0.008  -0.024  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.220   0.025   0.004  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.087   1.176   0.058  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.291   1.179   0.032  1.00  0.00           C  
HETATM    9  H1  UNL     1       2.826  -0.825  -0.754  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.784   1.006  -0.484  1.00  0.00           H  
HETATM   11  H3  UNL     1       2.875  -0.191   0.927  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.828  -2.109  -0.251  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.661  -2.096  -0.202  1.00  0.00           H  
HETATM   14  H6  UNL     1      -3.658  -0.046   0.935  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.660   2.091   0.145  1.00  0.00           H  
HETATM   16  H8  UNL     1       0.838   2.115   0.099  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    8
CONECT    3    4   12
CONECT    4    5    5   13
CONECT    5    6    7
CONECT    6   14
CONECT    7    8    8   15
CONECT    8   16
END
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SMILES for NP0001009 (p-Cresol)

CC1=CC=C(O)C=C1
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INCHI for NP0001009 (p-Cresol)

InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
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View in JSmol
Synonyms
ValueSource
1-Hydroxy-4-methylbenzeneChEBI
4-CresolChEBI
4-HydroxytolueneChEBI
4-MethylphenolChEBI
p-KresolChEBI
p-MethylphenolChEBI
p-Tolyl alcoholChEBI
ParacresolChEBI
1-Methyl-4-hydroxybenzeneHMDB
4-(Pentafluorosulfanyl)phenolHMDB
4-Methyl phenolHMDB
4-Methyl-phenolHMDB
p-CresylateHMDB
p-Cresylic acidHMDB
p-HydroxytolueneHMDB
p-Methyl phenolHMDB
p-MethylhydroxybenzeneHMDB
p-OxytolueneHMDB
p-ToluolHMDB
Paramethyl phenolHMDB
4-Cresol, potassium saltHMDB
m-CresolHMDB
4-Cresol, aluminum saltHMDB
4-Cresol, sodium saltHMDB
Para-cresolHMDB
Chemical FormulaC7H8O
Average Mass108.1378 Da
Monoisotopic Mass108.05751 Da
IUPAC Name4-methylphenol
Traditional NameP-cresol
CAS Registry Number106-44-5
SMILES
CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
InChI KeyIWDCLRJOBJJRNH-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
Artemisia capillarisLOTUS Database
Artemisia dracunculusFooDB
Artemisia jacuticaLOTUS Database
Artemisia macrocephalaLOTUS Database
Arum maculatumLOTUS Database
Aspalathus linearisLOTUS Database
Asparagus officinalisFooDB
Azadirachta indicaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica hirtaKNApSAcK Database
Bubalus bubalisFooDB
Campylobacter jejuni-
Cananga odorataLOTUS Database
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Cedronella canariensisLOTUS Database
CervidaeFooDB
Cervus canadensisFooDB
Chamaecyparis formosensisKNApSAcK Database
Cinnamomum aromaticumFooDB
Clostridium difficile-
Coffea arabicaKNApSAcK Database
Coffea arabica L.FooDB
ColumbaFooDB
ColumbidaeFooDB
Cucurbita maximaLOTUS Database
Daphne odoraLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Erigeron philadelphicusLOTUS Database
Gallus gallusFooDB
Giraffa camelopardalisLOTUS Database
Haplopteris anguste-elongataLOTUS Database
Jasminum grandiflorumPlant
Jasminum polyanthumLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melia azadirachKNApSAcK Database
Melia azedarachPlant
Mentha x piperitaFooDB
MorusFooDB
Morus spp.KNApSAcK Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Osmorhiza aristataLOTUS Database
Ovis ariesFooDB
Paeonia lactifloraLOTUS Database
Paeonia suffruticosaLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Pimpinella anisumKNApSAcK Database
Pittosporum balfouriiLOTUS Database
Podocarpus fasciculusKNApSAcK Database
Prangos uechtritziiLOTUS Database
Prunus armeniacaLOTUS Database
Prunus cerasusFooDB
Prunus dulcisFooDB
Pueraria montanaLOTUS Database
Rubus idaeusFooDB
Sasa albo-marginataKNApSAcK Database
Saxifraga stoloniferaLOTUS Database
Saxifraga stolonifera Meerb.KNApSAcK Database
Scutellaria baicalensisLOTUS Database
Senecio vulgarisKNApSAcK Database
Sinapis albaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tamarindus indicaFooDB
Thujopsis dolabrataLOTUS Database
Vaccinium corymbosumFooDB
Vaccinium myrtillusFooDB
Viburnum cylindricumLOTUS Database
Vitis viniferaLOTUS Database
Vittaria anguste-elongataKNApSAcK Database
Xanthium strumariumLOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Feces)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as para cresols. Para cresols are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassCresols
Direct ParentPara cresols
Alternative Parents
Substituents
  • P-cresol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point35.5 °CNot Available
Boiling Point201.80 to 202.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility21.5 mg/mL at 25 °CNot Available
LogP1.94Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility23.1 g/LALOGPS
logP1.95ALOGPS
logP2.18ChemAxon
logS-0.67ALOGPS
pKa (Strongest Acidic)10.36ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.08 m³·mol⁻¹ChemAxon
Polarizability11.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001858
DrugBank IDDB01688
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008789
KNApSAcK IDC00002645
Chemspider ID13839082
KEGG Compound IDC01468
BioCyc IDCPD-108
BiGG IDNot Available
Wikipedia LinkP-cresol
METLIN ID4236
PubChem Compound2879
PDB IDNot Available
ChEBI ID17847
Good Scents IDrw1003851
References
General References
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  8. Letelier ME, Rodriguez E, Wallace A, Lorca M, Repetto Y, Morello A, Aldunate J: Trypanosoma cruzi: a possible control of transfusion-induced Chagas' disease by phenolic antioxidants. Exp Parasitol. 1990 Nov;71(4):357-63. [PubMed:2121515 ]
  9. Nishiyama T, Ohnishi J, Hashiguchi Y: Fused heterocyclic antioxidants: antioxidative activities of hydrocoumarins in a homogeneous solution. Biosci Biotechnol Biochem. 2001 May;65(5):1127-33. [PubMed:11440127 ]
  10. Dills RL, Bellamy GM, Kalman DA: Quantitation of o-, m- and p-cresol and deuterated analogs in human urine by gas chromatography with electron capture detection. J Chromatogr B Biomed Sci Appl. 1997 Dec 5;703(1-2):105-13. [PubMed:9448067 ]
  11. Bammens B, Verbeke K, Vanrenterghem Y, Evenepoel P: Evidence for impaired assimilation of protein in chronic renal failure. Kidney Int. 2003 Dec;64(6):2196-203. [PubMed:14633143 ]
  12. Brunet P, Dou L, Cerini C, Berland Y: Protein-bound uremic retention solutes. Adv Ren Replace Ther. 2003 Oct;10(4):310-20. [PubMed:14681860 ]
  13. Vanholder R, De Smet R, Lesaffer G: p-cresol: a toxin revealing many neglected but relevant aspects of uraemic toxicity. Nephrol Dial Transplant. 1999 Dec;14(12):2813-5. [PubMed:10570076 ]
  14. Lameire N, Vanholder R, De Smet R: Uremic toxins and peritoneal dialysis. Kidney Int Suppl. 2001 Feb;78:S292-7. doi: 10.1046/j.1523-1755.2001.59780292.x. [PubMed:11169029 ]
  15. 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 ]
  16. Passmore IJ, Letertre MPM, Preston MD, Bianconi I, Harrison MA, Nasher F, Kaur H, Hong HA, Baines SD, Cutting SM, Swann JR, Wren BW, Dawson LF: Para-cresol production by Clostridium difficile affects microbial diversity and membrane integrity of Gram-negative bacteria. PLoS Pathog. 2018 Sep 12;14(9):e1007191. doi: 10.1371/journal.ppat.1007191. eCollection 2018 Sep. [PubMed:30208103 ]
  17. Patel M, Fowler D, Sizer J, Walton C: Faecal volatile biomarkers of Clostridium difficile infection. PLoS One. 2019 Apr 15;14(4):e0215256. doi: 10.1371/journal.pone.0215256. eCollection 2019. [PubMed:30986230 ]