Livestock Metabolome Database: Showing metabocard for p-Cresol sulfate (LMDB00566)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:52:41 UTC

Update Date

2016-07-20 21:04:17 UTC

Lmdb

LMDB00566

Secondary Accession Numbers

None

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 and is often considered to be a uremic toxin. Uremic toxins include low-molecular-weight compounds such as indoxyl sulfate, p-cresol 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.

Structure

MOL SDF PDB SMILES InChI

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

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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
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	Yes	ChemAxon
MDDR-like Rule	Yes	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-053r-8900000000-d93b8dfbd273b034801f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-11570a4a776bcf5ec9c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-7338e81b9250096b6fc5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004r-9800000000-ac89c33600013a77c141	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-c3c2c7c1b4570035b39f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9700000000-d79f4e77126c3cf9ae26	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ae3f3f10d7ec0a17d107	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-1a8286d1aadcdc168ec6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-1a8286d1aadcdc168ec6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05o0-9400000000-b79e09b3601b2f9c758d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	22059599	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0011635

FooDB ID

FDB028333

Phenol Explorer ID

Not Available

KNApSAcK ID

C00052378

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

3806481

ChEBI ID

82914

PubChem Compound ID

4615423

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB 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. [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. [18941347 ]

Showing metabocard for p-Cresol sulfate (LMDB00566)

Structure for LMDB00566 (p-Cresol sulfate)