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Record Information
Version3.6
Creation Date2013-07-09 16:10:00 UTC
Update Date2016-02-11 08:16:15 UTC
HMDB IDHMDB60967
Secondary Accession NumbersNone
Metabolite Identification
Common NameS-nirvanol
DescriptionS-nirvanol is a metabolite of mephenytoin. Mephenytoin (marketed as Mesantoin by Novartis) is a hydantoin, used as an anticonvulsant. It was introduced approximately 10 years after phenytoin, in the late 1940s. The significant metabolite of mephenytoin is nirvanol (5-ethyl-5-phenylhydantoin), which was the first hydantoin (briefly used as a hypnotic). However, nirvanol is quite toxic and mephenytoin was only considered after other less toxic anticonvulsants had failed. It can cause potentially fatal blood dyscrasia in 1% of patients. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H12N2O2
Average Molecular Weight204.2252
Monoisotopic Molecular Weight204.089877638
IUPAC Name(4S)-4-ethyl-4-phenyl-4H-imidazole-2,5-diol
Traditional Name(5S)-5-ethyl-5-phenylimidazole-2,4-diol
CAS Registry NumberNot Available
SMILES
CC[C@]1(N=C(O)N=C1O)C1=CC=CC=C1
InChI Identifier
InChI=1/C11H12N2O2/c1-2-11(8-6-4-3-5-7-8)9(14)12-10(15)13-11/h3-7H,2H2,1H3,(H2,12,13,14,15)/t11-/s2
InChI KeyInChIKey=UDTWZFJEMMUFLC-LDGXTIHJNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as ureides. These are compounds containing an ureide group with the general structure R1-CO-NH-CO-N(R)2R3, formally derived by the acylation of urea.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic carbonic acids and derivatives
Sub ClassUreas
Direct ParentUreides
Alternative Parents
Substituents
  • Ureide
  • Benzenoid
  • Monocyclic benzene moiety
  • Imidazole
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 Solubility0.27 mg/mLALOGPS
logP1.3ALOGPS
logP2.69ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.49ChemAxon
pKa (Strongest Basic)-0.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.18 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.68 m3·mol-1ChemAxon
Polarizability20.9 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00278
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60967
Metagene LinkHMDB60967
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available