Human Metabolome Database: Showing metabocard for p-Cresol sulfate (HMDB0011635)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2009-01-30 15:08:14 UTC

Update Date

2020-02-26 21:35:31 UTC

HMDB ID

HMDB0011635

Secondary Accession Numbers

HMDB11635

Metabolite Identification

Common Name

p-Cresol sulfate

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 ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
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

Chemical Formula

C₇H₈O₄S

Average Molecular Weight

188.201

Monoisotopic Molecular Weight

188.014329434

IUPAC Name

(4-methylphenyl)oxidanesulfonic acid

Traditional Name

(4-methylphenyl)oxidanesulfonic acid

CAS Registry Number

3233-58-7

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 Key

WGNAKZGUSRVWRH-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Arylsulfates

Direct Parent

Phenylsulfates

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aryl sulfate (CHEBI:82914 )

Ontology

Dermal

Enteral:

Ingestion

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Source:

Endogenous

Biological:

Microbe:

Clostridium:

Clostridium difficile

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.58 g/L	ALOGPS
logP	-0.55	ALOGPS
logP	1.71	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.07 m³·mol⁻¹	ChemAxon
Polarizability	17.17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified		Not Available	Not Available	Normal		details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected and Quantified	14.22 +/- 6.23 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	1.3 (0.3-5.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22827565	details
Urine	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22932811	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	217.85 +/- 69.08 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected and Quantified	261.0 +/- 75.5 uM	Adult (>18 years old)	Both	Hemodialysis	18045861	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Crohn's disease	19491857	details
Urine	Detected and Quantified	1.104 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details

Associated Disorders and Diseases

Disease References

Hemodialysis
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
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
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
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
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

114500 (Colorectal cancer)
266600 (Crohn's disease)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028333

KNApSAcK ID

Not Available

Chemspider ID

3806481

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4615423

PDB ID

Not Available

ChEBI ID

82914

Food Biomarker Ontology

Not Available

VMH ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]

Showing metabocard for p-Cresol sulfate (HMDB0011635)

Structure for HMDB0011635 (p-Cresol sulfate)