5-(4-hydroxyphenyl)-5-phenylhydantoin (CHEM045764)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 13:40:03 UTC
Update Date2016-11-09 01:23:24 UTC
Accession NumberCHEM045764
Identification
Common Name5-(4-hydroxyphenyl)-5-phenylhydantoin
ClassSmall Molecule
DescriptionA imidazolidine-2,4-dione that consists of hydantoin bearing phenyl and 4-hydroxyphenyl substituents at position 5.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass268.267 g/mol
Monoisotopic Mass268.085 g/mol
CAS Registry Number2784-27-2
IUPAC Name4-(4-hydroxyphenyl)-4-phenyl-4H-imidazole-2,5-diol
Traditional Name5-(4-hydroxyphenyl)-5-phenylimidazole-2,4-diol
SMILESOC1=NC(C(O)=N1)(C1=CC=CC=C1)C1=CC=C(O)C=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-36fb012770300fb47b89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0910000000-81a35adeb459b9224a95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900000000-a813694dc7e1cf8740c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-bd7cd943428e7be367e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9330000000-2c2090cefb411296eb0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-16f823d8b48ce7469f21Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0041905
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID16756
ChEBI ID63804
PubChem Compound ID17732
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1298726
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20664118
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=4008572
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=4049465
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6619238
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=6716263
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=6740735
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=6874875
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=7333696
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=9444669
11. 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.
12. 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.
13. 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.
14. Chou RC, Levy G: Effect of pregnancy on the pharmacokinetics of phenytoin in rats. J Pharmacol Exp Ther. 1984 May;229(2):351-8.
15. 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.
16. 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.
17. 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.
18. 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.