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Showing metabocard for p-Cresol (HMDB0001858)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-22 10:50:16 UTC
Update Date2023-02-21 17:15:50 UTC
HMDB IDHMDB0001858
Secondary Accession Numbers
  • HMDB0013762
  • HMDB01858
  • HMDB13762
Metabolite Identification
Common Namep-Cresol
Description
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001858 (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
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3D MOL for HMDB0001858 (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
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3D SDF for HMDB0001858 (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>
HMDB0001858

> <DATABASE_NAME>
hmdb

> <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 HMDB0001858 (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
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PDB for HMDB0001858 (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 HMDB0001858 (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 HMDB0001858 (p-Cresol)

CC1=CC=C(O)C=C1
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INCHI for HMDB0001858 (p-Cresol)

InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC7H8O
Average Molecular Weight108.1378
Monoisotopic Molecular Weight108.057514878
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
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
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationEnvironmental roleBiological roleIndirect biological role
Physical Properties
StateSolid
Experimental Molecular 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,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Fibroblasts
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Hemodialysis
  1. De Smet R, Van Kaer J, Liebich H, Lesaffer G, Verstraete A, Dhondt A, Duym P, Lameire N, Vanholder R: Heparin-induced release of protein-bound solutes during hemodialysis is an in vitro artifact. Clin Chem. 2001 May;47(5):901-9. [PubMed:11325895 ]
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  3. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  4. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  2. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Crohn's disease
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Enteritis
  1. Probert CS, Jones PR, Ratcliffe NM: A novel method for rapidly diagnosing the causes of diarrhoea. Gut. 2004 Jan;53(1):58-61. [PubMed:14684577 ]
Clostridium difficile infection
  1. 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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Colorectal cancer
  1. Cheng Y, Xie G, Chen T, Qiu Y, Zou X, Zheng M, Tan B, Feng B, Dong T, He P, Zhao L, Zhao A, Xu LX, Zhang Y, Jia W: Distinct urinary metabolic profile of human colorectal cancer. J Proteome Res. 2012 Feb 3;11(2):1354-63. doi: 10.1021/pr201001a. Epub 2011 Dec 28. [PubMed:22148915 ]
  2. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  3. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDDB01688
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDPCRESOL
MarkerDB IDMDB00000347
Good Scents IDrw1003851
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References