Livestock Metabolome Database: Showing metabocard for p-Cresol glucuronide (LMDB00567)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:52:42 UTC

Update Date

2016-07-20 21:04:18 UTC

Lmdb

LMDB00567

Secondary Accession Numbers

None

Metabolite Identification

Common Name

p-Cresol glucuronide

Description

p-Cresol glucuronide is a glucuronide derivative a p-Cresol that is typically excreted in the urine. P-Cresol (the precursor of p-cresol sulfate (PCS) and p-cresol glucuronide (PCG)) is mainly generated as an end product of tyrosine biotransformation by anaerobic intestinal bacteria. During passage through the colonic mucosa and liver, sulfatation and glucuronidation generates p-Cresol sulfate (as the most preponderant metabolite) and p-Cresol glucuronide (at markedly lower concentrations) (PMID: 23826225 ). Cresols are known as methylphenols. Cresols are used to dissolve other chemicals, such as disinfectants and deodorizers. They are also used to make specific chemicals that kill insect pests. Cresol solutions are used as household cleaners and disinfectants such as Lysol. Cresol solutions can also be found in photographic developers. In the past, cresol solutions have been used as antiseptics in surgery, but they have been largely displaced in this role by less toxic compounds. Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in brown mixtures such as creosote, cresolene and cresylic acids, which are wood preservatives. Microbes in the soil and water produce cresols when they break down materials in the environment. Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting. Cresols are also a chemical component found in Sharpie Markers. P-cresol is a major component in pig odor.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid	ChEBI
Cresol glucuronide	ChEBI
Cresyl glucuronide	ChEBI
Cresylglucuronide	ChEBI
p-Cresyl glucuronide	ChEBI
p-Cresyl-beta-D-glucuronide	ChEBI
p-Cresylglucuronide	ChEBI
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylate	Generator
p-Cresyl-b-D-glucuronide	Generator
p-Cresyl-β-D-glucuronide	Generator
4-Methylphenyl beta-D-glucopyranosiduronate	HMDB
4-Methylphenyl beta-D-glucopyranosiduronic acid	HMDB
pCG	HMDB
4-Cresylglucuronide	HMDB
p-Tolyl b-D-glucuronide	HMDB
p-Tolyl β-D-glucuronide	HMDB
p-Cresol glucuronide	ChEBI

Chemical Formula

C₁₃H₁₆O₇

Average Molecular Weight

284.2619

Monoisotopic Molecular Weight

284.089602866

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1

InChI Identifier

InChI=1S/C13H16O7/c1-6-2-4-7(5-3-6)19-13-10(16)8(14)9(15)11(20-13)12(17)18/h2-5,8-11,13-16H,1H3,(H,17,18)/t8-,9-,10+,11-,13+/m0/s1

InChI Key

JPAUCQAJHLSMQW-XPORZQOISA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Phenoxy compound
Phenol ether
Beta-hydroxy acid
Toluene
Monocyclic benzene moiety
Hydroxy acid
Monosaccharide
Benzenoid
Oxane
Pyran
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	-0.45	ALOGPS
logP	0.24	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.09 m³·mol⁻¹	ChemAxon
Polarizability	27.44 Å³	ChemAxon
Number of Rings	2	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9740000000-72c74a4f612ab1d96b3c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0a4i-3111590000-c4085ee51e3627835f9c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-8900000000-125953bb33ef62310b55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9500000000-c65eb13127918057773b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03e9-4920000000-31cc7062997a091bd192	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0980000000-0c28ed49edf3ac01b1e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0910000000-9e86725c906b8cb1ca73	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9700000000-7c668dc4ccf5c2f1df52	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053r-1790000000-8e41a0062d8b43c11986	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1920000000-2c0bc993f06c27f10d87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-078071ef7d6ab4f0ed4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05n0-0690000000-21c7e95f0396cfbeb2cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1920000000-d2d499346dfdb60bcd5c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9500000000-5890de451e5c75c51696	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053r-0790000000-26241f9e17537357950e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-4910000000-9f376fa7de7498124a4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9600000000-469910059aa1c2c999fd	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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	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	Porcine	21761043	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0011686

FooDB ID

FDB028373

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

135751

ChEBI ID

87986

PubChem Compound ID

154035

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

Liabeuf S, Glorieux G, Lenglet A, Diouf M, Schepers E, Desjardins L, Choukroun G, Vanholder R, Massy ZA: Does p-cresylglucuronide have the same impact on mortality as other protein-bound uremic toxins? PLoS One. 2013 Jun 24;8(6):e67168. doi: 10.1371/journal.pone.0067168. Print 2013. [23826225 ]

Showing metabocard for p-Cresol glucuronide (LMDB00567)

Structure for LMDB00567 (p-Cresol glucuronide)