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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2009-01-30 15:08:14 UTC |
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Update Date | 2020-11-09 23:18:29 UTC |
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HMDB ID | HMDB0011635 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | p-Cresol sulfate |
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Description | p-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 ). |
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Structure | |
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Synonyms | Value | Source |
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4-Cresol sulfate | ChEBI | Sulfuric acid mono-p-tolyl ester | ChEBI | 4-Cresol sulfuric acid | Generator | 4-Cresol sulphate | Generator | 4-Cresol sulphuric acid | Generator | Sulfate mono-p-tolyl ester | Generator | Sulphate mono-p-tolyl ester | Generator | Sulphuric acid mono-p-tolyl ester | Generator | p-Cresol sulfuric acid | Generator | p-Cresol sulphate | Generator | p-Cresol sulphuric acid | Generator | mono(4-Methylphenyl) sulfate | HMDB | p-Cresyl sulfate | HMDB | p-Cresyl sulphate | HMDB | p-Cresyl-sulfate | HMDB | p-Cresyl-sulphate | HMDB | p-Cresylsulfate | HMDB | p-Cresylsulphate | HMDB | p-Tolyl sulfate (6ci,7ci) | HMDB | p-Tolyl sulphate (6ci,7ci) | HMDB | Para-cresol sulfate | HMDB | Para-cresol sulphate | HMDB | Sulfuric acid mono(p-tolyl) ester (8ci) | HMDB | Sulfuric acid, mono(4-methylphenyl) ester | MeSH |
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Chemical Formula | C7H8O4S |
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Average Molecular Weight | 188.201 |
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Monoisotopic Molecular Weight | 188.014329434 |
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IUPAC Name | (4-methylphenyl)oxidanesulfonic acid |
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Traditional Name | (4-methylphenyl)oxidanesulfonic acid |
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CAS Registry Number | 3233-58-7 |
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SMILES | CC1=CC=C(OS(O)(=O)=O)C=C1 |
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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) |
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InChI Key | WGNAKZGUSRVWRH-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic sulfuric acids and derivatives |
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Sub Class | Arylsulfates |
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Direct Parent | Phenylsulfates |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: Source: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004m-7970000000-1d52a5deeb555385dd84 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004m-7970000000-1d52a5deeb555385dd84 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4r-5900000000-a697bdc119a940cbfd87 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-053r-8900000000-d93b8dfbd273b034801f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-9b2c2e9cce622bbce4d0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4r-1900000000-9e92c57df7e82ededa95 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fb9-9200000000-e8e0a9477934a6c4a93c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-7983b119ea08e1ce64db | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-956ac4acd6542c4e75d1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-6900000000-2dae39fab819632545a9 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 14.22 +/- 6.23 uM | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 1.3 (0.3-5.5) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 217.85 +/- 69.08 uM | Adult (>18 years old) | Both | uremia | | details | Blood | Detected and Quantified | 261.0 +/- 75.5 uM | Adult (>18 years old) | Both | Hemodialysis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Crohn's disease | | details | Urine | Detected and Quantified | 1.104 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details |
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Associated Disorders and Diseases |
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Disease References | Hemodialysis |
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- Pham NM, Recht NS, Hostetter TH, Meyer TW: Removal of the protein-bound solutes indican and p-cresol sulfate by peritoneal dialysis. Clin J Am Soc Nephrol. 2008 Jan;3(1):85-90. Epub 2007 Nov 28. [PubMed:18045861 ]
| Uremia |
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- 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 ]
| Colorectal cancer |
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- 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 ]
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Crohn's disease |
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- Williams HR, Cox IJ, Walker DG, North BV, Patel VM, Marshall SE, Jewell DP, Ghosh S, Thomas HJ, Teare JP, Jakobovits S, Zeki S, Welsh KI, Taylor-Robinson SD, Orchard TR: Characterization of inflammatory bowel disease with urinary metabolic profiling. Am J Gastroenterol. 2009 Jun;104(6):1435-44. doi: 10.1038/ajg.2009.175. Epub 2009 Apr 28. [PubMed:19491857 ]
| Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB028333 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 3806481 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 4615423 |
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PDB ID | Not Available |
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ChEBI ID | 82914 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - 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 ]
- 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 ]
- 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. [PubMed:2394806 ]
- 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 ]
- 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 ]
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