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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:32:56 UTC
HMDB IDHMDB15444
Secondary Accession NumbersNone
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
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 KeyInChIKey=UYXAWHWODHRRMR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as barbituric acid derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentBarbituric acid derivatives
Alternative Parents
Substituents
  • Barbiturate
  • Ureide
  • 1,3-diazinane
  • Urea
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Adjuvants
  • Barbiturates
  • GABA Modulators
  • Hypnotics and Sedatives
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.51e+00 g/LNot Available
LogP1.98SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility1.51 mg/mLALOGPS
logP1.8ALOGPS
logP1.25ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.48 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity61.95 m3·mol-1ChemAxon
Polarizability24.14 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-05cu-9310000000-eeec363075c613d35696View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01355
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01355
  • Not Applicable
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
NuGOwiki LinkHMDB15444
Metagene LinkHMDB15444
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. [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. [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. [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. [15577260 ]