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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:46 UTC
HMDB IDHMDB0014892
Secondary Accession Numbers
  • HMDB14892
Metabolite Identification
Common NameEthotoin
DescriptionEthotoin is a hydantoin derivative and anticonvulsant. Ethotoin exerts an antiepileptic effect without causing general central nervous system depression. The mechanism of action is probably very similar to that of phenytoin. The latter drug appears to stabilize rather than to raise the normal seizure threshold, and to prevent the spread of seizure activity rather than to abolish the primary focus of seizure discharges.
Structure
Data?1582753232
Synonyms
ValueSource
(+-)-3-Ethyl-5-phenylhydantoinChEBI
1-Ethyl-2,5-dioxo-4-phenylimidazolidineChEBI
3-Ethyl-5-phenyl-2,4-imidazolidinedioneChEBI
3-Ethyl-5-phenyl-imidazolidine-2,4-dioneChEBI
3-Ethyl-5-phenylhydantoinChEBI
3-Ethyl-5-phenylimidazolidin-2,4-dioneChEBI
EthotoineChEBI
EthotoinumChEBI
EtotoinaChEBI
AccenonKegg
PeganoneKegg
Abbott brand OF ethotoinHMDB
Chemical FormulaC11H12N2O2
Average Molecular Weight204.2252
Monoisotopic Molecular Weight204.089877638
IUPAC Name3-ethyl-5-phenylimidazolidine-2,4-dione
Traditional Nameethotoin
CAS Registry Number86-35-1
SMILES
CCN1C(=O)NC(C1=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H12N2O2/c1-2-13-10(14)9(12-11(13)15)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,15)
InChI KeySZQIFWWUIBRPBZ-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 Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point94 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.38 g/LNot Available
LogP0.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.38 g/LALOGPS
logP1.11ALOGPS
logP1.07ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)11.29ChemAxon
pKa (Strongest Basic)-8.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.41 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.05 m³·mol⁻¹ChemAxon
Polarizability20.68 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]+147.4431661259
DarkChem[M-H]-147.44531661259
DeepCCS[M+H]+145.60230932474
DeepCCS[M-H]-143.20730932474
DeepCCS[M-2H]-176.90430932474
DeepCCS[M+Na]+151.61130932474
AllCCS[M+H]+145.532859911
AllCCS[M+H-H2O]+141.332859911
AllCCS[M+NH4]+149.532859911
AllCCS[M+Na]+150.632859911
AllCCS[M-H]-147.532859911
AllCCS[M+Na-2H]-147.732859911
AllCCS[M+HCOO]-148.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EthotoinCCN1C(=O)NC(C1=O)C1=CC=CC=C12924.6Standard polar33892256
EthotoinCCN1C(=O)NC(C1=O)C1=CC=CC=C11813.5Standard non polar33892256
EthotoinCCN1C(=O)NC(C1=O)C1=CC=CC=C11835.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethotoin,1TMS,isomer #1CCN1C(=O)C(C2=CC=CC=C2)N([Si](C)(C)C)C1=O1822.7Semi standard non polar33892256
Ethotoin,1TMS,isomer #1CCN1C(=O)C(C2=CC=CC=C2)N([Si](C)(C)C)C1=O1926.2Standard non polar33892256
Ethotoin,1TMS,isomer #1CCN1C(=O)C(C2=CC=CC=C2)N([Si](C)(C)C)C1=O2531.1Standard polar33892256
Ethotoin,1TBDMS,isomer #1CCN1C(=O)C(C2=CC=CC=C2)N([Si](C)(C)C(C)(C)C)C1=O2051.1Semi standard non polar33892256
Ethotoin,1TBDMS,isomer #1CCN1C(=O)C(C2=CC=CC=C2)N([Si](C)(C)C(C)(C)C)C1=O2146.5Standard non polar33892256
Ethotoin,1TBDMS,isomer #1CCN1C(=O)C(C2=CC=CC=C2)N([Si](C)(C)C(C)(C)C)C1=O2623.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethotoin EI-B (Non-derivatized)splash10-0udi-6980000000-86b5edde33787fa5b3d52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethotoin EI-B (Non-derivatized)splash10-0zfr-4920000000-137fae4223f8b51dd5cd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethotoin CI-B (Non-derivatized)splash10-0a4i-1190000000-3ade8f65bbabe08f852a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethotoin CI-B (Non-derivatized)splash10-0udi-1190000000-56ad3615dcbc3fbecdbc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethotoin EI-B (Non-derivatized)splash10-0udi-6980000000-86b5edde33787fa5b3d52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethotoin EI-B (Non-derivatized)splash10-0zfr-4920000000-137fae4223f8b51dd5cd2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethotoin CI-B (Non-derivatized)splash10-0a4i-1190000000-3ade8f65bbabe08f852a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethotoin CI-B (Non-derivatized)splash10-0udi-1190000000-56ad3615dcbc3fbecdbc2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethotoin GC-MS (Non-derivatized) - 70eV, Positivesplash10-053f-4900000000-890da1feecbdd89e13202017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethotoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-6920000000-01714c9dcd6c4cf023622014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethotoin LC-ESI-qTof , Positive-QTOFsplash10-0a4i-1900000000-f71513d432cabc6ae5962017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethotoin , positive-QTOFsplash10-0a4i-1900000000-f71513d432cabc6ae5962017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 10V, Positive-QTOFsplash10-0a4i-0690000000-2b14fabe2a8a38bfd87a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 20V, Positive-QTOFsplash10-0zfr-2920000000-b4abc6e3540650b9fc2c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 40V, Positive-QTOFsplash10-0pb9-6900000000-ce4d6190e87bedc270a92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 10V, Negative-QTOFsplash10-0udi-0890000000-bc1ed1767185b47b35db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 20V, Negative-QTOFsplash10-0ugi-6930000000-d8856c4e6ba455c064082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 40V, Negative-QTOFsplash10-0udi-8900000000-81cbbd6924131f65bccf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 10V, Positive-QTOFsplash10-0a4i-0390000000-d37f36d7d55fd839b0052021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 20V, Positive-QTOFsplash10-0apl-5930000000-d012a03e319c8a7a1e802021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 40V, Positive-QTOFsplash10-0l06-9600000000-f553fba04ea2221422e62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 10V, Negative-QTOFsplash10-0udi-0290000000-0795d967a430c0f6e2ae2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 20V, Negative-QTOFsplash10-0f96-8910000000-a36978bebfc33440a2722021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethotoin 40V, Negative-QTOFsplash10-0006-9400000000-f6e409587ccb41c14d582021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 DB00754 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00754 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00754
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3176
KEGG Compound IDC07839
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthotoin
METLIN IDNot Available
PubChem Compound3292
PDB IDNot Available
ChEBI ID4888
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. SCHWADE ED, RICHARDS RK, EVERETT GM: Peganone, a new antiepileptic drug. Dis Nerv Syst. 1956 May;17(5):155-8. [PubMed:13317788 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular weight:
226937.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Lenkowski PW, Ko SH, Anderson JD, Brown ML, Patel MK: Block of human NaV1.5 sodium channels by novel alpha-hydroxyphenylamide analogues of phenytoin. Eur J Pharm Sci. 2004 Apr;21(5):635-44. [PubMed:15066664 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]