P. aeruginosa Metabolome Database: p-Cresol (PAMDB001747)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB001747

Identification

Name:

p-Cresol

Description:

p-Cresol, also known as 4-methylphenol or 4-hydroxytoluene, is a positional isomer of cresol. The other two isomers are m-cresol and o-cresol. (Wikipedia) 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). p-Cresol has been reported to affect several biochemical, biological and physiological functions: for example, it alters cell membrane permeability in bacteria. (HMDB, PMID 10570076) In Pseudomonas aeruginosa, p-Cresol can be produced as a by-product of thiazole biosynthesis. (EcoCyc)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

1-Hydroxy-4-methylbenzene
1-Methyl-4-hydroxybenzene
4-(Pentafluorosulfanyl)phenol
4-(Pentafluorosulphanyl)phenol
4-Cresol
4-Hydroxytoluene
4-methyl phenol
4-Methyl-Phenol
4-Methylphenol
4-Methylphenol ( p-cresol)
p-cresol
Cresol, para
P-Cresol
P-Cresol (4-methylphenol)
P-Cresol 98+ %
P-Cresol for synthesis
P-Cresol Hydrate 90 %
P-Cresol Hydric acid 90 %
P-Cresylate
P-Cresylic acid
P-Hydroxytoluene
P-Kresol
P-Methyl phenol
P-Methylhydroxybenzene
P-Methylphenol
P-Oxytoluene
P-Toluol
P-Tolyl alcohol
Paracresol
Paramethyl phenol
Phenol, 4-methyI

Chemical Formula:

C₇H₈O

Average Molecular Weight:

108.1378

Monoisotopic Molecular Weight:

108.057514878

InChI Key:

IWDCLRJOBJJRNH-UHFFFAOYSA-N

InChI:

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

CAS number:

106-44-5

IUPAC Name:

4-methylphenol

Traditional IUPAC Name:

P-cresol

SMILES:

CC1=CC=C(O)C=C1

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as para cresols. These are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenols and derivatives

Direct Parent

Para cresols

Alternative Parents

Substituents

P-cresol
Toluene
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cresol (CHEBI:17847 )
a methylphenol (CPD-108 )

Physical Properties

State:

Solid

Charge:

Melting point:

35.5 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	21.5 mg/mL at 25 deg C	PhysProp
LogP:	1.94; 1.94 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	23.1 mg/mL	ALOGPS
logP	1.95	ALOGPS
logP	2.18	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Acidic)	10.36	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.08 m³·mol^-1	ChemAxon
Polarizability	11.93 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

S-Adenosylmethionine + NADPH + L-Tyrosine > p-Cresol + 5'-Deoxyadenosine + Dehydroglycine + Hydrogen ion + L-Methionine + NADP
L-Tyrosine + S-Adenosylmethionine + a reduced electron acceptor > Dehydroglycine + p-Cresol + 5'-Deoxyadenosine + L-Methionine + an oxidized electron acceptor + Hydrogen ion
L-Tyrosine + S-Adenosylmethionine + NADPH <> 2-iminoacetate + p-Cresol + 5'-Deoxyadenosine + L-Methionine + NADP + Hydrogen ion
L-Tyrosine + NADPH + S-adenosyl-L-methionine + L-Tyrosine + NADPH > Hydrogen ion + NADP + L-Methionine + 5'-Deoxyadenosine + p-Cresol + 2-iminoacetate

Pathways:

Metabolic pathways pae01100
Thiamine metabolism pae00730

Spectra

Spectra:

Not Available

References

References:

Akasaka K, Ohrui H, Meguro H, Tamura M: Determination of triacylglycerol and cholesterol ester hydroperoxides in human plasma by high-performance liquid chromatography with fluorometric postcolumn detection. J Chromatogr. 1993 Aug 11;617(2):205-11. Pubmed: 8408385
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
Bone E, Tamm A, Hill M: The production of urinary phenols by gut bacteria and their possible role in the causation of large bowel cancer. Am J Clin Nutr. 1976 Dec;29(12):1448-54. Pubmed: 826152
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
Buhlmann P, Hayakawa M, Ohshiro T, Amemiya S, Umezawa Y: Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes. Anal Chem. 2001 Jul 15;73(14):3199-205. Pubmed: 11476216
Cork A, Park KC: Identification of electrophysiologically-active compounds for the malaria mosquito, Anopheles gambiae, in human sweat extracts. Med Vet Entomol. 1996 Jul;10(3):269-76. Pubmed: 8887339
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
Geyer H, Scheunert I, Korte F: Bioconcentration potential of organic environmental chemicals in humans. Regul Toxicol Pharmacol. 1986 Dec;6(4):313-47. Pubmed: 3101145
Gostner A, Blaut M, Schaffer V, Kozianowski G, Theis S, Klingeberg M, Dombrowski Y, Martin D, Ehrhardt S, Taras D, Schwiertz A, Kleessen B, Luhrs H, Schauber J, Dorbath D, Menzel T, Scheppach W: Effect of isomalt consumption on faecal microflora and colonic metabolism in healthy volunteers. Br J Nutr. 2006 Jan;95(1):40-50. Pubmed: 16441915
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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
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
Ogata N, Shibata T: Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins. Res Commun Mol Pathol Pharmacol. 2000;107(1-2):167-73. Pubmed: 11334365
Vanholder, R., De Smet, R., Lesaffer, G. (1999). "p-cresol: a toxin revealing many neglected but relevant aspects of uraemic toxicity." Nephrol Dial Transplant 14:2813-2815. Pubmed: 10570076

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	17847
HMDB ID	HMDB01858
Pubchem Compound ID	2879
Kegg ID	C01468
ChemSpider ID	13839082
Wikipedia	P-Cresol
BioCyc ID	CPD-108
EcoCyc ID	CPD-108
Ligand Expo	PCR

p-Cresol (PAMDB001747)

Structure for p-Cresol (PAMDB001747)