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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-13 11:47:09 UTC
Update Date2019-07-23 06:35:12 UTC
HMDB IDHMDB0041905
Secondary Accession Numbers
  • HMDB0060598
  • HMDB0060972
  • HMDB41905
  • HMDB60598
  • HMDB60972
Metabolite Identification
Common Name4-Hydroxyphenytoin
Description4-Hydroxyphenytoin, also known as hydroxyphenytoin or 4'-HPPH, belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. 4-Hydroxyphenytoin is a metabolite of the anti-seizure medication phenytoin (PHT) and is excreted in the urine (PMID: 15855726 ).
Structure
Data?1563863712
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)-isomerHMDB
4'-HPPHHMDB
4-HPPHHMDB
Hydroxyphenytoin, (+-)-isomerHMDB
Hydroxyphenytoin, (S)-isomerHMDB
Hydroxyphenytoin, 11C-labeledHMDB
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 Number2784-27-2
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
Description belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
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

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.70Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity73.21 m³·mol⁻¹ChemAxon
Polarizability26.77 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-005c-2970000000-f2362aeb837caff92396Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-5026900000-a7352e0820321c5e2123Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0290000000-2299e419930e3a97862cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0960000000-45490c2de987f0b93b2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi1-1900000000-31738f367353e34a82bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2090000000-e526de0cd9ea6ea5c67bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9010000000-61cd151f31d096cf0b46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-8a074704ab6b4e05587eSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.305 (0.522-2.386) uMAdult (>18 years old)Female
Epilepsy
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID16756
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound17732
PDB IDNot Available
ChEBI ID63804
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zeng J, Liu D, Zou Y: [High performance liquid chromatographic determination of hydroxyphenytoin in human urine]. Hua Xi Yi Ke Da Xue Xue Bao. 1992 Sep;23(3):321-4. [PubMed:1298726 ]
  2. Shimada K, Wakabayashi H, Sato A: Gas chromatographic determination of m- and p-hydroxyphenytoin in the urine of epileptic patients. J Chromatogr. 1985 May 3;339(2):331-7. [PubMed:4008572 ]
  3. Jurgens U: Routine determination of hydroxyphenytoin in urine by high-performance liquid chromatography using an automatic column-switching technique. J Chromatogr. 1983 Jul 8;275(2):335-43. [PubMed:6619238 ]
  4. Chou RC, Levy G: Effect of pregnancy on the pharmacokinetics of phenytoin in rats. J Pharmacol Exp Ther. 1984 May;229(2):351-8. [PubMed:6716263 ]
  5. Rambeck B, May T: Urinary hydroxyphenytoin/creatinine ratios as an index of compliance in adult epileptic patients on phenytoin therapy. Ther Drug Monit. 1984;6(2):164-72. [PubMed:6740735 ]
  6. Sato A, Shimada K, Izumo Y, Sakaguchi T: High-performance liquid chromatographic determination of phenytoin and hydroxyphenytoin in human urine. J Chromatogr. 1983 Jun 10;275(1):97-105. [PubMed:6874875 ]
  7. Horsmans Y, Van den Berge V, Bouckaert A, Desager JP: Phenytoin hydroxylation in a healthy Caucasian population: bimodal distribution of hydroxyphenytoin urinary excretion. Pharmacol Toxicol. 1997 Dec;81(6):276-9. [PubMed:9444669 ]
  8. Yamanaka H, Nakajima M, Hara Y, Katoh M, Tachibana O, Yamashita J, Yokoi T: Urinary excretion of phenytoin metabolites, 5-(4'-hydroxyphenyl)-5-phenylhydantoin and its O-glucuronide in humans and analysis of genetic polymorphisms of UDP-glucuronosyltransferases. Drug Metab Pharmacokinet. 2005 Apr;20(2):135-43. [PubMed:15855726 ]