Record Information
Version1.0
Creation date2011-09-21 01:38:45 UTC
Update date2017-03-11 23:00:42 UTC
Primary IDFDB028373
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namep-Cresol glucuronide
Descriptionp-Cresol glucuronide is a glucuronide derivative a p-Cresol that is typically excreted in the urine. 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 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. [HMDB]
CAS Number17680-99-8
Structure
Thumb
Synonyms
SynonymSource
(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
P-Cresyl glucuronideHMDB
P-Cresyl-beta-D-glucuronideHMDB
P-CresylglucuronideHMDB
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC13H16O7
IUPAC name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methylphenoxy)oxane-2-carboxylic acid
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
Isomeric SMILESCC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1
Average Molecular Weight284.2619
Monoisotopic Molecular Weight284.089602866
Classification
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
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Foods
  • Dairy products
  • Eggs
  • Meats
  • Grains:

    Nuts and legumes:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9740000000-72c74a4f612ab1d96b3cJSpectraViewer
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0a4i-3111590000-c4085ee51e3627835f9cJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0980000000-0c28ed49edf3ac01b1e4JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0910000000-9e86725c906b8cb1ca73JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9700000000-7c668dc4ccf5c2f1df52JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-1790000000-8e41a0062d8b43c11986JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1920000000-2c0bc993f06c27f10d87JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-078071ef7d6ab4f0ed4cJSpectraViewer
    ChemSpider ID135751
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound ID154035
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB11686
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    Enzymes
    NameGene NameUniProt ID
    UDP-glucuronosyltransferase 2B4UGT2B4P06133
    UDP-glucuronosyltransferase 1-4UGT1A4P22310
    UDP-glucuronosyltransferase 2B7UGT2B7P16662
    UDP-glucuronosyltransferase 1-1UGT1A1P22309
    UDP-glucuronosyltransferase 1-9UGT1A9O60656
    UDP-glucuronosyltransferase 1-6UGT1A6P19224
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference