You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:22 UTC
Update Date2017-10-23 19:06:13 UTC
HMDB IDHMDB0013894
Secondary Accession Numbers
  • HMDB13894
Metabolite Identification
Common NameS-4-Hydroxymephenytoin
DescriptionS-4-Hydroxymephenytoin is only found in individuals that have used or taken Mephenytoin. S-4-Hydroxymephenytoin is a metabolite of Mephenytoin. S-4-hydroxymephenytoin belongs to the family of Ureides. These are compounds containing an ureide group with the general structure R-CO-NH-CO-N(R)R'', formally derived by the acylation of urea.
Structure
Thumb
Synonyms
ValueSource
4-Hydroxymephenytoin, (S)-isomerMeSH
Para-hydroxymephenytoinMeSH
Chemical FormulaC12H14N2O3
Average Molecular Weight234.2512
Monoisotopic Molecular Weight234.100442324
IUPAC Name5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione
Traditional Name5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione
CAS Registry NumberNot Available
SMILES
CCC1(NC(=O)N(C)C1=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C12H14N2O3/c1-3-12(8-4-6-9(15)7-5-8)10(16)14(2)11(17)13-12/h4-7,15H,3H2,1-2H3,(H,13,17)
InChI KeyOQPLORUDZLXXPD-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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Industrial application:

  Pharmaceutical industry:

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 Solubility3.71 g/LALOGPS
logP1.08ALOGPS
logP1.36ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.64 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.52 m³·mol⁻¹ChemAxon
Polarizability23.68 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i1-1920000000-7afcd60942dd73d5a2feView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0096-2590000000-f2cc0a8f7eec622f615eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0390000000-0c74607072d5df473d4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0940000000-ecd23b96737a2da30042View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-4900000000-91ee5eff3db1f2867e1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-77b066a7e80bd2325f4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-6290000000-0b31de4400248d9df176View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-51ddbfd0c12456ae47e3View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00057
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID106722
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound119507
PDB IDNot Available
ChEBI ID838827
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available