p-Cresol glucuronide (CHEM022661)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:45:46 UTC
Update Date2016-11-09 01:17:33 UTC
Accession NumberCHEM022661
Identification
Common Namep-Cresol glucuronide
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acidChEBI
Cresol glucuronideChEBI
Cresyl glucuronideChEBI
CresylglucuronideChEBI
p-Cresyl glucuronideChEBI
p-Cresyl-beta-D-glucuronideChEBI
p-CresylglucuronideChEBI
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylateGenerator
p-Cresyl-b-D-glucuronideGenerator
p-Cresyl-β-D-glucuronideGenerator
4-Methylphenyl beta-D-glucopyranosiduronateHMDB
4-Methylphenyl beta-D-glucopyranosiduronic acidHMDB
pCGHMDB
4-CresylglucuronideHMDB
p-Tolyl b-D-glucuronideHMDB
p-Tolyl β-D-glucuronideHMDB
p-Cresol glucuronideChEBI
Chemical FormulaC13H16O7
Average Molecular Mass284.262 g/mol
Monoisotopic Mass284.090 g/mol
CAS Registry NumberNot Available
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
SMILESCC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1
InChI IdentifierInChI=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 KeyJPAUCQAJHLSMQW-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic 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 FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility24 g/LALOGPS
logP-0.45ALOGPS
logP0.24ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity65.09 m³·mol⁻¹ChemAxon
Polarizability27.44 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9740000000-72c74a4f612ab1d96b3cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-3111590000-c4085ee51e3627835f9cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8900000000-125953bb33ef62310b55Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9500000000-c65eb13127918057773bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03e9-4920000000-31cc7062997a091bd192Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0980000000-0c28ed49edf3ac01b1e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0910000000-9e86725c906b8cb1ca73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9700000000-7c668dc4ccf5c2f1df52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-1790000000-8e41a0062d8b43c11986Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1920000000-2c0bc993f06c27f10d87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-078071ef7d6ab4f0ed4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n0-0690000000-21c7e95f0396cfbeb2ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1920000000-d2d499346dfdb60bcd5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9500000000-5890de451e5c75c51696Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-0790000000-26241f9e17537357950eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4910000000-9f376fa7de7498124a4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-469910059aa1c2c999fdSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0011686
FooDB IDFDB028373
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID135751
ChEBI ID87986
PubChem Compound ID154035
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15314235
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16337285
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19810771
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19961175
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21620604
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22089538
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22520047
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23826225
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25131851