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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-12-07 02:51:10 UTC
HMDB IDHMDB0015444
Secondary Accession Numbers
  • HMDB15444
Metabolite Identification
Common NameHexobarbital
DescriptionHexobarbital is only found in individuals that have used or taken this drug. It is a barbiturate that is effective as a hypnotic and sedative. [PubChem]Hexobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABA-A receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Structure
Thumb
Synonyms
ValueSource
5-(1-Cyclohexen-1-yl)-1,5-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-(1-Cyclohexen-1-yl)-1,5-dimethylbarbituric acidChEBI
5-Cyclohex-1-enyl-1,5-dimethyl-pyrimidine-2,4,6-trioneChEBI
EvipanChEBI
HexobarbitoneChEBI
MethexenylChEBI
MethylhexabitalChEBI
5-(1-Cyclohexen-1-yl)-1,5-dimethylbarbitateGenerator
5-(1-Cyclohexen-1-yl)-1,5-dimethylbarbitic acidGenerator
HexenalMeSH
Hexobarbital, sodiumMeSH
Sodium hexobarbitalMeSH
Chemical FormulaC12H16N2O3
Average Molecular Weight236.267
Monoisotopic Molecular Weight236.116092388
IUPAC Name5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
Traditional Namehexobarbital
CAS Registry Number56-29-1
SMILES
CN1C(=O)NC(=O)C(C)(C1=O)C1=CCCCC1
InChI Identifier
InChI=1S/C12H16N2O3/c1-12(8-6-4-3-5-7-8)9(15)13-11(17)14(2)10(12)16/h6H,3-5,7H2,1-2H3,(H,13,15,17)
InChI KeyUYXAWHWODHRRMR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDiazines
Direct ParentPyrimidones
Alternative Parents
Substituents
  • Pyrimidone
  • Ureide
  • Hydropyrimidine
  • 1,2,5,6-tetrahydropyrimidine
  • Dicarboximide
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Observation:

  Health condition:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.51 g/LNot Available
LogP1.98SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility1.51 g/LALOGPS
logP1.8ALOGPS
logP1.25ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity61.95 m³·mol⁻¹ChemAxon
Polarizability24.14 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00gi-9420000000-001b8f1462933b4fb9c1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-3940000000-827e61b1deec4916f579View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1190000000-58f9b3cb0025cd8911aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2920000000-e4d6ce12b6d33fff56d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9100000000-55244be11c0d8667c413View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-7980000000-db4b09996693417c3e09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-5900000000-3fac68a4cc2e19e26087View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-8495751984d2901a8826View in MoNA
MSMass Spectrum (Electron Ionization)splash10-05cu-9310000000-eeec363075c613d35696View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01355 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01355 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01355
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3482
KEGG Compound IDC11723
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHexobarbital
METLIN IDNot Available
PubChem Compound3608
PDB IDNot Available
ChEBI ID5706
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Korkmaz S, Ljungblad E, Wahlstrom G: Interaction between flumazenil and the anesthetic effects of hexobarbital in the rat. Brain Res. 1995 Apr 10;676(2):371-7. [PubMed:7614008 ]
  2. Dall V, Orntoft U, Schmidt A, Nordholm L: Interaction of the competitive AMPA receptor antagonist NBQX with hexobarbital. Pharmacol Biochem Behav. 1993 Sep;46(1):73-6. [PubMed:8255925 ]
  3. Wahlstrom G: A study of the duration of acute tolerance induced with hexobarbital in male rats. Pharmacol Biochem Behav. 1998 Apr;59(4):945-8. [PubMed:9586853 ]
  4. Takenoshita R, Toki S: [New aspects of hexobarbital metabolism: stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases]. Yakugaku Zasshi. 2004 Dec;124(12):857-71. [PubMed:15577260 ]