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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-01-30 15:08:14 UTC

Update Date

2023-02-21 17:17:32 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8669.9598668.884   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.6248668.114   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.2908668.884   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.9568668.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8665.9568666.574   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8667.2908665.804   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8668.6248666.574   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8661.9408665.802   0.000  0.00  0.00           O+0
HETATM    9  S   UNK     0    8663.2818666.578   0.000  0.00  0.00           S+0
HETATM   10  O   UNK     0    8664.0498667.913   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8662.5088667.913   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8664.6198665.802   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    3    7    1                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    9                                                            
CONECT    9   10   11   12    8                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9    5                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

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	HMDB

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

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18045861)
Saliva (PMID: 22308371)
Cerebrospinal Fluid (CSF) (PMID: 31726035)

Organ

Placenta (HMDB: HMDB0011635)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27275383)

Cellular substructure

Cytoplasm (HMDB: HMDB0011635)
Extracellular (HMDB: HMDB0011635)

Source

Exogenous

Exogenous (HMDB: HMDB0011635)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Meats (HMDB: HMDB0011635)
Legumes (HMDB: HMDB0011635)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0011635)

Nut

Nuts (HMDB: HMDB0011635)

Milk and milk product

Dairy products (HMDB: HMDB0011635)

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Egg

Eggs (HMDB: HMDB0011635)

Soy

Soy (HMDB: HMDB0011635)

Endogenous

Endogenous (HMDB: HMDB0011635)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0011635)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.587	31661259
DarkChem	[M-H]-	140.256	31661259
DeepCCS	[M+H]+	138.712	30932474
DeepCCS	[M-H]-	136.02	30932474
DeepCCS	[M-2H]-	172.289	30932474
DeepCCS	[M+Na]+	147.812	30932474
AllCCS	[M+H]+	139.3	32859911
AllCCS	[M+H-H2O]+	134.9	32859911
AllCCS	[M+NH4]+	143.3	32859911
AllCCS	[M+Na]+	144.4	32859911
AllCCS	[M-H]-	133.9	32859911
AllCCS	[M+Na-2H]-	134.9	32859911
AllCCS	[M+HCOO]-	136.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.02 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5413 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.16 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1491.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	429.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	145.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	277.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	466.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	553.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	154.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1016.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	387.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1243.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	344.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	454.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	233.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	120.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Cresol sulfate	CC1=CC=C(OS(O)(=O)=O)C=C1	2436.9	Standard polar	33892256
p-Cresol sulfate	CC1=CC=C(OS(O)(=O)=O)C=C1	1473.1	Standard non polar	33892256
p-Cresol sulfate	CC1=CC=C(OS(O)(=O)=O)C=C1	1593.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
p-Cresol sulfate,1TMS,isomer #1	CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	1594.7	Semi standard non polar	33892256
p-Cresol sulfate,1TMS,isomer #1	CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	1612.0	Standard non polar	33892256
p-Cresol sulfate,1TMS,isomer #1	CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C)C=C1	2243.4	Standard polar	33892256
p-Cresol sulfate,1TBDMS,isomer #1	CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	1834.0	Semi standard non polar	33892256
p-Cresol sulfate,1TBDMS,isomer #1	CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	1868.3	Standard non polar	33892256
p-Cresol sulfate,1TBDMS,isomer #1	CC1=CC=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C1	2331.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - p-Cresol sulfate GC-EI-TOF (Non-derivatized)	splash10-004m-7970000000-1d52a5deeb555385dd84	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Cresol sulfate GC-EI-TOF (Non-derivatized)	splash10-004m-7970000000-1d52a5deeb555385dd84	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Cresol sulfate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-5900000000-a697bdc119a940cbfd87	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Cresol sulfate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - p-Cresol sulfate LC-ESI-IT , negative-QTOF	splash10-053r-8900000000-d93b8dfbd273b034801f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - p-Cresol sulfate 40V, Negative-QTOF	splash10-004i-9000000000-11570a4a776bcf5ec9c3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - p-Cresol sulfate 10V, Negative-QTOF	splash10-000i-0900000000-7338e81b9250096b6fc5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - p-Cresol sulfate 20V, Negative-QTOF	splash10-004r-9800000000-ac89c33600013a77c141	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 10V, Positive-QTOF	splash10-000i-0900000000-9b2c2e9cce622bbce4d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 20V, Positive-QTOF	splash10-0a4r-1900000000-9e92c57df7e82ededa95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 40V, Positive-QTOF	splash10-0fb9-9200000000-e8e0a9477934a6c4a93c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 10V, Negative-QTOF	splash10-000i-0900000000-7983b119ea08e1ce64db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 20V, Negative-QTOF	splash10-0a4i-0900000000-956ac4acd6542c4e75d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 40V, Negative-QTOF	splash10-0a4i-6900000000-2dae39fab819632545a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 10V, Positive-QTOF	splash10-000i-0900000000-c3c2c7c1b4570035b39f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 20V, Positive-QTOF	splash10-0006-9700000000-d79f4e77126c3cf9ae26	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 40V, Positive-QTOF	splash10-0006-9000000000-ae3f3f10d7ec0a17d107	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 10V, Negative-QTOF	splash10-000i-0900000000-1a8286d1aadcdc168ec6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 20V, Negative-QTOF	splash10-000i-0900000000-1a8286d1aadcdc168ec6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Cresol sulfate 40V, Negative-QTOF	splash10-05o0-9400000000-b79e09b3601b2f9c758d	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	27.099 +/- 13.28 uM	Adult (>18 years old)	Both	Normal	31726035	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.12 +/- 0.12 uM	Adult (>18 years old)	Both	Normal	31726035	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	14.22 +/- 6.23 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22827565	details
Urine	Detected and Quantified	1.3 (0.3-5.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	261.0 +/- 75.5 uM	Adult (>18 years old)	Both	Hemodialysis	18045861	details
Blood	Detected and Quantified	217.85 +/- 69.08 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected and Quantified	35.60 +/- 22.32 uM	Adult (>18 years old)	Both	Parkinson’s disease	31726035	details
Blood	Detected and Quantified	40.91 +/- 22.85 uM	Adult (>18 years old)	Both	Parkinson’s disease with motor fluctuation	31726035	details
Blood	Detected and Quantified	21.79 +/- 7.44 uM	Adult (>18 years old)	Both	Parkinson’s disease without motor fluctuation	31726035	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.32 +/- 0.53 uM	Adult (>18 years old)	Both	Parkinson’s disease	31726035	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.60 +/- 0.50 uM	Adult (>18 years old)	Both	Parkinson’s disease with motor fluctuation	31726035	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.16 +/- 0.11 uM	Adult (>18 years old)	Both	Parkinson’s disease without motor fluctuation	31726035	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	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	Analysis of 30 no...	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
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

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

C00052378

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

PCS

MarkerDB ID

Not Available

Good Scents 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 ]
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 ]
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 ]
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)

MOL for HMDB0011635 (p-Cresol sulfate)

3D MOL for HMDB0011635 (p-Cresol sulfate)

3D SDF for HMDB0011635 (p-Cresol sulfate)

3D-SDF for HMDB0011635 (p-Cresol sulfate)

PDB for HMDB0011635 (p-Cresol sulfate)

3D PDB for HMDB0011635 (p-Cresol sulfate)

SMILES for HMDB0011635 (p-Cresol sulfate)

INCHI for HMDB0011635 (p-Cresol sulfate)

Structure for HMDB0011635 (p-Cresol sulfate)

3D Structure for HMDB0011635 (p-Cresol sulfate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra