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Record Information
Version3.6
Creation Date2013-07-22 19:52:34 UTC
Update Date2017-03-02 22:05:48 UTC
HMDB IDHMDB61174
Secondary Accession NumbersNone
Metabolite Identification
Common Namep-Hydroxyl-ethotoin
Descriptionp-Hydroxyl-ethotoin is a metabolite of ethotoin. Ethotoin (marketed as Peganone by Ovation) is an anticonvulsant drug used in the treatment of epilepsy. It is a hydantoin, similar to phenytoin. Ethotoin lacks phenytoin's side effects of gingival hyperplasia and hirsutism, however it is less effective. This, combined with the need for frequent dosing has limited its usefulness. Ethotoin is no longer widely used. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H12N2O3
Average Molecular Weight220.2246
Monoisotopic Molecular Weight220.08479226
IUPAC Name3-ethyl-5-(4-hydroxyphenyl)imidazolidine-2,4-dione
Traditional Name3-ethyl-5-(4-hydroxyphenyl)imidazolidine-2,4-dione
CAS Registry NumberNot Available
SMILES
CCN1C(=O)NC(C1=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C11H12N2O3/c1-2-13-10(15)9(12-11(13)16)7-3-5-8(14)6-4-7/h3-6,9,14H,2H2,1H3,(H,12,16)
InChI KeyUUBDNHDPPHJUHB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassAzolidines
Direct ParentPhenylhydantoins
Alternative Parents
Substituents
  • 5-phenylhydantoin
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • N-acyl urea
  • Phenol
  • Ureide
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboximide
  • Carbonic acid derivative
  • Urea
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.65 mg/mLALOGPS
logP0.81ALOGPS
logP0.76ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.64 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57.03 m3·mol-1ChemAxon
Polarizability21.81 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
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
      DrugBank Metabolite IDDBMET00979
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB61174
      Metagene LinkHMDB61174
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available