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Record Information
Version4.0
Creation Date2013-07-09 16:10:17 UTC
Update Date2017-09-23 15:00:25 UTC
HMDB IDHMDB0060972
Secondary Accession Numbers
  • HMDB60972
StatusExpected but not Quantified
Metabolite Identification
Common Name4'-HPPH
Description4'-HPPH is a metabolite of phenytoin. Phenytoin sodium is a commonly used antiepileptic. Phenytoin acts to suppress the abnormal brain activity seen in seizure by reducing electrical conductance among brain cells by stabilizing the inactive state of voltage-gated sodium channels. Aside from seizures, it is an option in the treatment of trigeminal neuralgia in the event that carbamazepine or other first-line treatment seems inappropriate. It is sometimes considered a class 1b antiarrhythmic. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
(Hydroxyphenyl)phenylhydantoinChEBI
(P-Hydroxyphenyl)phenylhydantoinChEBI
4-HydroxydiphenylhydantoinChEBI
5-(4'-Hydroxyphenyl)-5-phenylhydantoinChEBI
5-(P-Hydroxyphenyl)-5-phenylhydantoinChEBI
HydroxydiphenylhydantoinChEBI
HydroxyphenytoinChEBI
P-HydroxydiphenylhydantoinChEBI
P-HydroxyphenytoinChEBI
Para-hydroxyphenytoinChEBI
5-(4-Hydroxyphenyl)-5-phenyl-2,4-imidazolidinedioneHMDB
5-(4-Hydroxyphenyl)-5-phenylhydantoinHMDB
5-(P-Hydroxyphenyl)-5-phenyl-hydantoinHMDB
Hydroxyphenytoin, (R)-isomerMeSH
4'-HPPHMeSH
4-HPPHMeSH
Hydroxyphenytoin, (+-)-isomerMeSH
Hydroxyphenytoin, (S)-isomerMeSH
Hydroxyphenytoin, 11C-labeledMeSH
Chemical FormulaC15H12N2O3
Average Molecular Weight268.2674
Monoisotopic Molecular Weight268.08479226
IUPAC Name4-(4-hydroxyphenyl)-4-phenyl-4H-imidazole-2,5-diol
Traditional Name5-(4-hydroxyphenyl)-5-phenylimidazole-2,4-diol
CAS Registry NumberNot Available
SMILES
OC1=NC(C(O)=N1)(C1=CC=CC=C1)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C15H12N2O3/c18-12-8-6-11(7-9-12)15(10-4-2-1-3-5-10)13(19)16-14(20)17-15/h1-9,18H,(H2,16,17,19,20)
InChI KeyXEEDURHPFVXALT-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
  • Diphenylmethane
  • 5-phenylhydantoin
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • 5-monosubstituted hydantoin
  • 1-hydroxy-2-unsubstituted benzenoid
  • N-acyl urea
  • Phenol
  • Ureide
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition
Biological Location:
Source:
Subcellular:
Biofluid and excreta:
Organ and components:
Role
Biological role:
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 Solubility0.12 mg/mLALOGPS
logP2.01ALOGPS
logP3.1ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area85.41 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity73.21 m3·mol-1ChemAxon
Polarizability26.77 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00284
      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 LinkHMDB0060972
      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