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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-09-16 08:19:02 UTC
Update Date2017-12-07 02:25:14 UTC
HMDB IDHMDB0010350
Secondary Accession Numbers
  • HMDB10350
Metabolite Identification
Common Name2-Phenylethanol glucuronide
Description2-Phenylethanol glucuronide is a natural human metabolite of 2-phenylethanol generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.
Structure
Thumb
Synonyms
ValueSource
2-Phenylethanol glucuronosideHMDB
Chemical FormulaC14H18O7
Average Molecular Weight298.2885
Monoisotopic Molecular Weight298.10525293
IUPAC Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-phenylethoxy)oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-phenylethoxy)oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)[C@H](OCCC2=CC=CC=C2)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C14H18O7/c15-9-10(16)12(13(18)19)21-14(11(9)17)20-7-6-8-4-2-1-3-5-8/h1-5,9-12,14-17H,6-7H2,(H,18,19)/t9-,10-,11+,12-,14+/m0/s1
InChI KeyHIXLLXLCNONZRH-BYNIDDHOSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Benzenoid
  • Monosaccharide
  • Pyran
  • Oxane
  • Secondary alcohol
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Origin
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.4 g/LALOGPS
logP-0.44ALOGPS
logP0.044ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.91 m³·mol⁻¹ChemAxon
Polarizability29.45 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9640000000-eecc4dcb70dd8251abc7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00di-4112490000-e82b09b317fe8c5deb11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0390000000-be4a0988839d36f4574cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0910000000-874f8489ab3fedb1ba54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6900000000-ffb9f5c3d98cdf2aed39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-2590000000-3f66e87ad3a71d42c808View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-4930000000-dd38513c568bd279df05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9500000000-4b7faec75f8f8bbaf43fView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FoodDB IDFDB027502
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC03033
      BioCyc IDBeta-D-Glucuronides
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound24862077
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available

      Only showing the first 10 proteins. There are 18 proteins in total.

      Enzymes

      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
      Gene Name:
      UGT2B28
      Uniprot ID:
      Q9BY64
      Molecular weight:
      38742.9
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
      Gene Name:
      UGT2B4
      Uniprot ID:
      P06133
      Molecular weight:
      60512.035
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
      Gene Name:
      UGT1A4
      Uniprot ID:
      P22310
      Molecular weight:
      60024.535
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
      Gene Name:
      UGT2B7
      Uniprot ID:
      P16662
      Molecular weight:
      60720.15
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
      Gene Name:
      UGT2B15
      Uniprot ID:
      P54855
      Molecular weight:
      61035.815
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
      Gene Name:
      UGT2A1
      Uniprot ID:
      Q9Y4X1
      Molecular weight:
      60771.605
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
      Gene Name:
      UGT1A1
      Uniprot ID:
      P22309
      Molecular weight:
      59590.91
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
      Gene Name:
      UGT1A9
      Uniprot ID:
      O60656
      Molecular weight:
      59940.495
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
      Gene Name:
      UGT1A3
      Uniprot ID:
      P35503
      Molecular weight:
      60337.835
      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
      Gene Name:
      UGT2B17
      Uniprot ID:
      O75795
      Molecular weight:
      61094.915

      Only showing the first 10 proteins. There are 18 proteins in total.