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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-01-30 15:08:14 UTC
Update Date2022-03-07 02:51:12 UTC
HMDB IDHMDB0011635
Secondary Accession Numbers
  • HMDB11635
Metabolite Identification
Common Namep-Cresol sulfate
Descriptionp-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
Data?1582752931
Synonyms
ValueSource
4-Cresol sulfateChEBI
Sulfuric acid mono-p-tolyl esterChEBI
4-Cresol sulfuric acidGenerator
4-Cresol sulphateGenerator
4-Cresol sulphuric acidGenerator
Sulfate mono-p-tolyl esterGenerator
Sulphate mono-p-tolyl esterGenerator
Sulphuric acid mono-p-tolyl esterGenerator
p-Cresol sulfuric acidGenerator
p-Cresol sulphateGenerator
p-Cresol sulphuric acidGenerator
mono(4-Methylphenyl) sulfateHMDB
p-Cresyl sulfateHMDB
p-Cresyl sulphateHMDB
p-Cresyl-sulfateHMDB
p-Cresyl-sulphateHMDB
p-CresylsulfateHMDB
p-CresylsulphateHMDB
p-Tolyl sulfate (6ci,7ci)HMDB
p-Tolyl sulphate (6ci,7ci)HMDB
Para-cresol sulfateHMDB
Para-cresol sulphateHMDB
Sulfuric acid mono(p-tolyl) ester (8ci)HMDB
Sulfuric acid, mono(4-methylphenyl) esterHMDB
Chemical FormulaC7H8O4S
Average Molecular Weight188.201
Monoisotopic Molecular Weight188.014329434
IUPAC Name(4-methylphenyl)oxidanesulfonic acid
Traditional Name(4-methylphenyl)oxidanesulfonic acid
CAS Registry Number3233-58-7
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 KeyWGNAKZGUSRVWRH-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassArylsulfates
Direct ParentPhenylsulfates
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP-0.55ALOGPS
logP1.71ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.07 m³·mol⁻¹ChemAxon
Polarizability17.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+142.58731661259
DarkChem[M-H]-140.25631661259
DeepCCS[M+H]+138.71230932474
DeepCCS[M-H]-136.0230932474
DeepCCS[M-2H]-172.28930932474
DeepCCS[M+Na]+147.81230932474
AllCCS[M+H]+139.332859911
AllCCS[M+H-H2O]+134.932859911
AllCCS[M+NH4]+143.332859911
AllCCS[M+Na]+144.432859911
AllCCS[M-H]-133.932859911
AllCCS[M+Na-2H]-134.932859911
AllCCS[M+HCOO]-136.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-Cresol sulfateCC1=CC=C(OS(O)(=O)=O)C=C12436.9Standard polar33892256
p-Cresol sulfateCC1=CC=C(OS(O)(=O)=O)C=C11473.1Standard non polar33892256
p-Cresol sulfateCC1=CC=C(OS(O)(=O)=O)C=C11593.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
p-Cresol sulfate,1TMS,isomer #1CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C11594.7Semi standard non polar33892256
p-Cresol sulfate,1TMS,isomer #1CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C11612.0Standard non polar33892256
p-Cresol sulfate,1TMS,isomer #1CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C12243.4Standard polar33892256
p-Cresol sulfate,1TBDMS,isomer #1CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C11834.0Semi standard non polar33892256
p-Cresol sulfate,1TBDMS,isomer #1CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C11868.3Standard non polar33892256
p-Cresol sulfate,1TBDMS,isomer #1CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C12331.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - p-Cresol sulfate GC-EI-TOF (Non-derivatized)splash10-004m-7970000000-1d52a5deeb555385dd842018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cresol sulfate GC-EI-TOF (Non-derivatized)splash10-004m-7970000000-1d52a5deeb555385dd842018-05-25HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Cresol sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-5900000000-a697bdc119a940cbfd872017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Cresol sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol sulfate LC-ESI-IT , negative-QTOFsplash10-053r-8900000000-d93b8dfbd273b034801f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol sulfate 40V, Negative-QTOFsplash10-004i-9000000000-11570a4a776bcf5ec9c32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol sulfate 10V, Negative-QTOFsplash10-000i-0900000000-7338e81b9250096b6fc52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol sulfate 20V, Negative-QTOFsplash10-004r-9800000000-ac89c33600013a77c1412021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 10V, Positive-QTOFsplash10-000i-0900000000-9b2c2e9cce622bbce4d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 20V, Positive-QTOFsplash10-0a4r-1900000000-9e92c57df7e82ededa952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 40V, Positive-QTOFsplash10-0fb9-9200000000-e8e0a9477934a6c4a93c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 10V, Negative-QTOFsplash10-000i-0900000000-7983b119ea08e1ce64db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 20V, Negative-QTOFsplash10-0a4i-0900000000-956ac4acd6542c4e75d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 40V, Negative-QTOFsplash10-0a4i-6900000000-2dae39fab819632545a92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 10V, Positive-QTOFsplash10-000i-0900000000-c3c2c7c1b4570035b39f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 20V, Positive-QTOFsplash10-0006-9700000000-d79f4e77126c3cf9ae262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 40V, Positive-QTOFsplash10-0006-9000000000-ae3f3f10d7ec0a17d1072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 10V, Negative-QTOFsplash10-000i-0900000000-1a8286d1aadcdc168ec62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 20V, Negative-QTOFsplash10-000i-0900000000-1a8286d1aadcdc168ec62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol sulfate 40V, Negative-QTOFsplash10-05o0-9400000000-b79e09b3601b2f9c758d2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified27.099 +/- 13.28 uMAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.12 +/- 0.12 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified14.22 +/- 6.23 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified1.3 (0.3-5.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified35.60 +/- 22.32 uMAdult (>18 years old)BothParkinson’s disease details
BloodDetected and Quantified40.91 +/- 22.85 uMAdult (>18 years old)BothParkinson’s disease with motor fluctuation details
BloodDetected and Quantified21.79 +/- 7.44 uMAdult (>18 years old)BothParkinson’s disease without motor fluctuation details
BloodDetected and Quantified217.85 +/- 69.08 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified261.0 +/- 75.5 uMAdult (>18 years old)BothHemodialysis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.32 +/- 0.53 uMAdult (>18 years old)BothParkinson’s disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.60 +/- 0.50 uMAdult (>18 years old)BothParkinson’s disease with motor fluctuation details
Cerebrospinal Fluid (CSF)Detected and Quantified0.16 +/- 0.11 uMAdult (>18 years old)BothParkinson’s disease without motor fluctuation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohn's disease details
UrineDetected and Quantified1.104 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
Associated Disorders and Diseases
Disease References
Hemodialysis
  1. 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
  1. 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
  1. 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 ]
  2. 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 ]
  3. 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
  1. 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
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028333
KNApSAcK IDC00052378
Chemspider ID3806481
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4615423
PDB IDNot Available
ChEBI ID82914
Food Biomarker OntologyNot Available
VMH IDPCS
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]