Showing Compound Card for 5,5-Diphenylimidazolid-4-one (CDB005740)

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Record Information
Version1.0
Created at2020-04-27 16:51:00 UTC
Updated at2021-01-04 18:49:13 UTC
CannabisDB IDCDB005740
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name5,5-Diphenylimidazolid-4-one
Description5,5-Diphenylimidazolid-4-one also known as Doxenitoin belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Doxenitoin has a phenytoin-like structure, the only difference being reduction of the carbonyl at the 2-position to a methylene group. Doxenitoin or 5,5-Diphenylimidazolid-4-one is a drug derived from phenytoin and has a significant anticonvulsant potency. It was developed as an antiepileptic agent (PMID: 13803201 ). 5,5-Diphenylimidazolid-4-one is moderately soluble in glacial acetic acid but practically insoluble in water. 5,5-Diphenylimidazolid-4-one is a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC15H14N2O
Average Molecular Weight238.29
Monoisotopic Molecular Weight238.1106
IUPAC Name5,5-diphenyl-2,5-dihydro-1H-imidazol-4-ol
Traditional Name5,5-diphenyl-1,2-dihydroimidazol-4-ol
CAS Registry Number3254-93-1
SMILES
OC1=NCNC1(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C15H14N2O/c18-14-15(17-11-16-14,12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,17H,11H2,(H,16,18)
InChI KeyFEJIIZAOQRTGPC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • Imidazolidinone
  • Imidazolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
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
logP1.9ALOGPS
logP2.69ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)2.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area44.62 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70 m³·mol⁻¹ChemAxon
Polarizability25.25 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5,5-Diphenylimidazolid-4-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5,5-Diphenylimidazolid-4-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5,5-Diphenylimidazolid-4-one, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID17588
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18622
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. BOUDIN G, BARBIZET J, LABRAM C: [Experimentation with a new antiepileptic drug derived from phenytoin: 5,5-diphenyltetrahydroimidazole-4-one (glior)]. Therapie. 1959;14:994-9. [PubMed:13803201 ]