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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-13 11:47:09 UTC
Update Date2021-09-14 15:45:32 UTC
HMDB IDHMDB0041905
Secondary Accession Numbers
  • HMDB0060598
  • HMDB0060972
  • HMDB41905
  • HMDB60598
  • HMDB60972
Metabolite Identification
Common Name4-Hydroxyphenytoin
Description4-Hydroxyphenytoin, also known as 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. In humans, 4-hydroxyphenytoin is involved in the metabolic disorder called the phenytoin (antiarrhythmic) action pathway. 4-Hydroxyphenytoin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 4-Hydroxyphenytoin.
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.70Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+162.23531661259
DarkChem[M-H]-160.71331661259
DeepCCS[M+H]+163.24630932474
DeepCCS[M-H]-160.88830932474
DeepCCS[M-2H]-193.77430932474
DeepCCS[M+Na]+169.33930932474
AllCCS[M+H]+161.532859911
AllCCS[M+H-H2O]+157.632859911
AllCCS[M+NH4]+165.132859911
AllCCS[M+Na]+166.232859911
AllCCS[M-H]-162.732859911
AllCCS[M+Na-2H]-162.032859911
AllCCS[M+HCOO]-161.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxyphenytoinOC1=NC(C(O)=N1)(C1=CC=CC=C1)C1=CC=C(O)C=C13767.8Standard polar33892256
4-HydroxyphenytoinOC1=NC(C(O)=N1)(C1=CC=CC=C1)C1=CC=C(O)C=C12309.5Standard non polar33892256
4-HydroxyphenytoinOC1=NC(C(O)=N1)(C1=CC=CC=C1)C1=CC=C(O)C=C12670.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyphenytoin,1TMS,isomer #1C[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O)C=C2)C(O)=N12498.1Semi standard non polar33892256
4-Hydroxyphenytoin,1TMS,isomer #2C[Si](C)(C)OC1=NC(O)=NC1(C1=CC=CC=C1)C1=CC=C(O)C=C12492.7Semi standard non polar33892256
4-Hydroxyphenytoin,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)N=C(O)N=C2O)C=C12558.6Semi standard non polar33892256
4-Hydroxyphenytoin,2TMS,isomer #1C[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O[Si](C)(C)C)C=C2)C(O)=N12505.3Semi standard non polar33892256
4-Hydroxyphenytoin,2TMS,isomer #2C[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O)C=C2)C(O[Si](C)(C)C)=N12448.5Semi standard non polar33892256
4-Hydroxyphenytoin,2TMS,isomer #3C[Si](C)(C)OC1=NC(O)=NC1(C1=CC=CC=C1)C1=CC=C(O[Si](C)(C)C)C=C12502.8Semi standard non polar33892256
4-Hydroxyphenytoin,3TMS,isomer #1C[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O[Si](C)(C)C)C=C2)C(O[Si](C)(C)C)=N12540.9Semi standard non polar33892256
4-Hydroxyphenytoin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O)C=C2)C(O)=N12722.2Semi standard non polar33892256
4-Hydroxyphenytoin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC(O)=NC1(C1=CC=CC=C1)C1=CC=C(O)C=C12717.9Semi standard non polar33892256
4-Hydroxyphenytoin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C2(C3=CC=CC=C3)N=C(O)N=C2O)C=C12795.1Semi standard non polar33892256
4-Hydroxyphenytoin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O)=N12926.0Semi standard non polar33892256
4-Hydroxyphenytoin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=N12851.6Semi standard non polar33892256
4-Hydroxyphenytoin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=NC(O)=NC1(C1=CC=CC=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12922.8Semi standard non polar33892256
4-Hydroxyphenytoin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(C2=CC=CC=C2)(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(O[Si](C)(C)C(C)(C)C)=N13072.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenytoin GC-MS (Non-derivatized) - 70eV, Positivesplash10-005c-2970000000-f2362aeb837caff923962017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenytoin GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-5026900000-a7352e0820321c5e21232017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyphenytoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 10V, Positive-QTOFsplash10-014i-0290000000-2299e419930e3a97862c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 20V, Positive-QTOFsplash10-00kb-0960000000-45490c2de987f0b93b2d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 40V, Positive-QTOFsplash10-0gi1-1900000000-31738f367353e34a82bf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 10V, Negative-QTOFsplash10-014i-2090000000-e526de0cd9ea6ea5c67b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 20V, Negative-QTOFsplash10-0006-9010000000-61cd151f31d096cf0b462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 40V, Negative-QTOFsplash10-0006-9300000000-8a074704ab6b4e05587e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 10V, Positive-QTOFsplash10-014i-0090000000-36fb012770300fb47b892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 20V, Positive-QTOFsplash10-001i-0910000000-81a35adeb459b9224a952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 40V, Positive-QTOFsplash10-001i-1900000000-a813694dc7e1cf8740c12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 10V, Negative-QTOFsplash10-014i-0090000000-bd7cd943428e7be367e72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 20V, Negative-QTOFsplash10-0006-9330000000-2c2090cefb411296eb0b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyphenytoin 40V, Negative-QTOFsplash10-0006-9500000000-16f823d8b48ce7469f212021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  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 ]