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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:04:18 UTC
Update Date2021-09-14 15:46:40 UTC
HMDB IDHMDB0060864
Secondary Accession Numbers
  • HMDB60864
Metabolite Identification
Common NamePhenytoin arene-oxide
DescriptionPhenytoin arene-oxide belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. Phenytoin acts to suppress the abnormal brain activity seen in seizure by reducing electrical conductance among brain cells by stabilizing the inactive state of voltage-gated sodium channels. Phenytoin arene-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, phenytoin arene-oxide participates in a number of enzymatic reactions. In particular, phenytoin arene-oxide can be biosynthesized from phenytoin; which is catalyzed by the enzymes cytochrome P450 2C19 and cytochrome P450 2C9. In addition, phenytoin arene-oxide can be converted into phenytoin dihydrodiol; which is mediated by the enzymes cytochrome P450 1A2, cytochrome P450 2C19, cytochrome P450 2E1, and epoxide hydrolase 1. Phenytoin arene-oxide is a metabolite of phenytoin. In humans, phenytoin arene-oxide is involved in the metabolic disorder called the phenytoin (antiarrhythmic) action pathway. It is sometimes considered a class 1b antiarrhythmic. Aside from seizures, it is an option in the treatment of trigeminal neuralgia in the event that carbamazepine or other first-line treatment seems inappropriate. Phenytoin sodium is a commonly used antiepileptic.
Structure
Data?1563866115
SynonymsNot Available
Chemical FormulaC15H12N2O3
Average Molecular Weight268.2674
Monoisotopic Molecular Weight268.08479226
IUPAC Name5-{7-oxabicyclo[4.1.0]hepta-2,4-dien-3-yl}-5-phenylimidazolidine-2,4-dione
Traditional Name5-{7-oxabicyclo[4.1.0]hepta-2,4-dien-3-yl}-5-phenylimidazolidine-2,4-dione
CAS Registry NumberNot Available
SMILES
O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC2OC2C=C1
InChI Identifier
InChI=1S/C15H12N2O3/c18-13-15(17-14(19)16-13,9-4-2-1-3-5-9)10-6-7-11-12(8-10)20-11/h1-8,11-12H,(H2,16,17,18,19)
InChI KeyWBRFFCOFWKCXFD-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
  • 5-monosubstituted hydantoin
  • N-acyl urea
  • Ureide
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboximide
  • Carbonic acid derivative
  • Urea
  • Azacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Carbonyl group
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP0.68ALOGPS
logP1ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.73 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity72.22 m³·mol⁻¹ChemAxon
Polarizability26.14 ųChemAxon
Number of Rings4ChemAxon
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]+164.07731661259
DarkChem[M-H]-156.22931661259
DeepCCS[M+H]+158.10930932474
DeepCCS[M-H]-155.75130932474
DeepCCS[M-2H]-188.64130932474
DeepCCS[M+Na]+164.20230932474
AllCCS[M+H]+162.432859911
AllCCS[M+H-H2O]+158.632859911
AllCCS[M+NH4]+166.032859911
AllCCS[M+Na]+167.032859911
AllCCS[M-H]-164.832859911
AllCCS[M+Na-2H]-164.132859911
AllCCS[M+HCOO]-163.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phenytoin arene-oxideO=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC2OC2C=C13887.8Standard polar33892256
Phenytoin arene-oxideO=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC2OC2C=C12399.2Standard non polar33892256
Phenytoin arene-oxideO=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC2OC2C=C12487.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenytoin arene-oxide,1TMS,isomer #1C[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O2649.8Semi standard non polar33892256
Phenytoin arene-oxide,1TMS,isomer #1C[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O2331.5Standard non polar33892256
Phenytoin arene-oxide,1TMS,isomer #1C[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O3665.8Standard polar33892256
Phenytoin arene-oxide,1TMS,isomer #2C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C12636.1Semi standard non polar33892256
Phenytoin arene-oxide,1TMS,isomer #2C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C12347.1Standard non polar33892256
Phenytoin arene-oxide,1TMS,isomer #2C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C13795.7Standard polar33892256
Phenytoin arene-oxide,2TMS,isomer #1C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O2417.7Semi standard non polar33892256
Phenytoin arene-oxide,2TMS,isomer #1C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O2408.9Standard non polar33892256
Phenytoin arene-oxide,2TMS,isomer #1C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O3299.8Standard polar33892256
Phenytoin arene-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O2934.1Semi standard non polar33892256
Phenytoin arene-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O2544.6Standard non polar33892256
Phenytoin arene-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O3737.3Standard polar33892256
Phenytoin arene-oxide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C12882.1Semi standard non polar33892256
Phenytoin arene-oxide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C12554.2Standard non polar33892256
Phenytoin arene-oxide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC2OC2C=C1)C1=CC=CC=C13798.9Standard polar33892256
Phenytoin arene-oxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O2927.8Semi standard non polar33892256
Phenytoin arene-oxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O2844.6Standard non polar33892256
Phenytoin arene-oxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC3OC3C=C2)(C2=CC=CC=C2)C1=O3353.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenytoin arene-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-3900000000-9efa4bfdf4f72f2f25142017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenytoin arene-oxide 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 - Phenytoin arene-oxide 10V, Positive-QTOFsplash10-014j-0890000000-b1ac67ebfe6d311563072017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin arene-oxide 20V, Positive-QTOFsplash10-0002-0900000000-798f9ccb530dd8c072822017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin arene-oxide 40V, Positive-QTOFsplash10-0fu6-3900000000-3c0913b08bb8cc2b39432017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin arene-oxide 10V, Negative-QTOFsplash10-014i-0090000000-2fd54e3b6725c2e1b6cb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin arene-oxide 20V, Negative-QTOFsplash10-014i-3390000000-68e5a4d4466d694c48752017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin arene-oxide 40V, Negative-QTOFsplash10-0f6x-4900000000-56adc3c0900052f75a892017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin arene-oxide 10V, Negative-QTOFsplash10-014i-0090000000-bd7cd943428e7be367e72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin arene-oxide 20V, Negative-QTOFsplash10-0006-9540000000-7cb9b44ddb94c50295812021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin arene-oxide 40V, Negative-QTOFsplash10-0006-9500000000-052a6f128f9a89805f402021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin arene-oxide 10V, Positive-QTOFsplash10-014i-0090000000-bab633482800eb8f5ea12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin arene-oxide 20V, Positive-QTOFsplash10-00ls-0950000000-76342d8c21289fc13d3e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin arene-oxide 40V, Positive-QTOFsplash10-0f8a-2910000000-c5d591694a524a0544072021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101592230
PDB IDNot Available
ChEBI IDNot Available
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