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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:42 UTC
HMDB IDHMDB0014673
Secondary Accession Numbers
  • HMDB14673
Metabolite Identification
Common NameMephenytoin
DescriptionMephenytoin, also known as mefenitoina or methylphenetoin, belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. Mephenytoin is a drug which is used for the treatment of refractory partial epilepsy. In humans, mephenytoin is involved in the ibuprofen action pathway. Mephenytoin 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 Mephenytoin.
Structure
Data?1582753206
Synonyms
ValueSource
DL-MephenytoinChEBI
MefenitoinaChEBI
MephenytoineChEBI
MephenytoinumChEBI
MethylphenetoinChEBI
PhenylethylmethylhydantoinChEBI
MesantoinKegg
MephentoinHMDB
Methyl hydantoinHMDB
5 Ethyl 3 methyl 5 phenylhydantoinMeSH, HMDB
5-Ethyl-3-methyl-5-phenylhydantoinMeSH, HMDB
Phenetoin, methylMeSH, HMDB
MethoinMeSH, HMDB
Methyl phenetoinMeSH, HMDB
PhenantoinMeSH, HMDB
MefenetoinMeSH, HMDB
Chemical FormulaC12H14N2O2
Average Molecular Weight218.2518
Monoisotopic Molecular Weight218.105527702
IUPAC Name5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
Traditional Namemephenytoin
CAS Registry Number50-12-4
SMILES
CCC1(NC(=O)N(C)C1=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)
InChI KeyGMHKMTDVRCWUDX-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
  • 5-phenylhydantoin
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • N-acyl urea
  • Ureide
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.97 g/LNot Available
LogP1.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.97 g/LALOGPS
logP1.64ALOGPS
logP1.67ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)11.18ChemAxon
pKa (Strongest Basic)-8.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.41 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.54 m³·mol⁻¹ChemAxon
Polarizability22.67 ųChemAxon
Number of Rings2ChemAxon
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]+151.30331661259
DarkChem[M-H]-149.61631661259
DeepCCS[M+H]+154.54730932474
DeepCCS[M-H]-152.18930932474
DeepCCS[M-2H]-185.08430932474
DeepCCS[M+Na]+160.6430932474
AllCCS[M+H]+148.232859911
AllCCS[M+H-H2O]+144.132859911
AllCCS[M+NH4]+152.132859911
AllCCS[M+Na]+153.232859911
AllCCS[M-H]-152.032859911
AllCCS[M+Na-2H]-152.132859911
AllCCS[M+HCOO]-152.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MephenytoinCCC1(NC(=O)N(C)C1=O)C1=CC=CC=C12878.0Standard polar33892256
MephenytoinCCC1(NC(=O)N(C)C1=O)C1=CC=CC=C11831.5Standard non polar33892256
MephenytoinCCC1(NC(=O)N(C)C1=O)C1=CC=CC=C11805.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mephenytoin,1TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C1868.6Semi standard non polar33892256
Mephenytoin,1TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C1892.9Standard non polar33892256
Mephenytoin,1TMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C2461.0Standard polar33892256
Mephenytoin,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C2094.5Semi standard non polar33892256
Mephenytoin,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C2133.2Standard non polar33892256
Mephenytoin,1TBDMS,isomer #1CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N1[Si](C)(C)C(C)(C)C2531.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Mephenytoin EI-B (Non-derivatized)splash10-0f79-2900000000-af8712fc36e2b911e9a82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mephenytoin EI-B (Non-derivatized)splash10-0f79-2900000000-af8712fc36e2b911e9a82018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mephenytoin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-1900000000-76ba03e4694ef29def3b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mephenytoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mephenytoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mephenytoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mephenytoin LC-ESI-qTof , Positive-QTOFsplash10-0159-3901000000-d726d8591f6fd6b87a0a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mephenytoin , positive-QTOFsplash10-0159-3901000000-d726d8591f6fd6b87a0a2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 10V, Positive-QTOFsplash10-014i-0490000000-8c8bcd12840df6ae00f22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 20V, Positive-QTOFsplash10-001i-0920000000-360996524b6c1cdc8fe32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 40V, Positive-QTOFsplash10-0ue9-6900000000-5f6a566d2e8972a3e79c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 10V, Negative-QTOFsplash10-014i-0290000000-de9e2d95bc7cf0aea9ac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 20V, Negative-QTOFsplash10-014i-7590000000-9cb9accf3f7737fa14832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 40V, Negative-QTOFsplash10-000x-9600000000-a00ec47fefbdc60a200a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 10V, Positive-QTOFsplash10-014i-0190000000-8b9cb11606c241146d8b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 20V, Positive-QTOFsplash10-00lr-1900000000-a867b49304e4c28141772021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 40V, Positive-QTOFsplash10-014i-6900000000-2fd710ba16d058127ae92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 10V, Negative-QTOFsplash10-014i-0090000000-4f94e1f66d72d6972b8a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 20V, Negative-QTOFsplash10-000i-2900000000-be298ddea23898cbfbc62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mephenytoin 40V, Negative-QTOFsplash10-01ox-6900000000-8676a25532452b4ac29b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00532 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00532 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00532
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3920
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMephenytoin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID6757
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 ReferencesNot Available