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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:59 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
Data?1582753298
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, HMDB
Hexobarbital, sodiumMeSH, HMDB
Sodium hexobarbitalMeSH, HMDB
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
Description Belongs to the class of organic compounds known as pyrimidones. Pyrimidones 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
Alternative Parents
Substituents
  • Pyrimidone
  • Hydropyrimidine
  • 1,2,5,6-tetrahydropyrimidine
  • Dicarboximide
  • Carbonic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point67.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point463.95 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.51 g/LNot Available
LogP1.98SANGSTER (1994)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.51 g/LALOGPS
logP1.8ALOGPS
logP1.25ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.41ChemAxon
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
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]+154.96231661259
DarkChem[M-H]-150.2731661259
DeepCCS[M+H]+157.38730932474
DeepCCS[M-H]-154.99230932474
DeepCCS[M-2H]-188.27630932474
DeepCCS[M+Na]+163.32730932474
AllCCS[M+H]+153.732859911
AllCCS[M+H-H2O]+149.932859911
AllCCS[M+NH4]+157.332859911
AllCCS[M+Na]+158.332859911
AllCCS[M-H]-156.732859911
AllCCS[M+Na-2H]-156.932859911
AllCCS[M+HCOO]-157.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HexobarbitalCN1C(=O)NC(=O)C(C)(C1=O)C1=CCCCC12968.6Standard polar33892256
HexobarbitalCN1C(=O)NC(=O)C(C)(C1=O)C1=CCCCC11770.3Standard non polar33892256
HexobarbitalCN1C(=O)NC(=O)C(C)(C1=O)C1=CCCCC11818.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hexobarbital,1TMS,isomer #1CN1C(=O)N([Si](C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O1956.3Semi standard non polar33892256
Hexobarbital,1TMS,isomer #1CN1C(=O)N([Si](C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O1948.2Standard non polar33892256
Hexobarbital,1TMS,isomer #1CN1C(=O)N([Si](C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O2611.4Standard polar33892256
Hexobarbital,1TBDMS,isomer #1CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O2179.9Semi standard non polar33892256
Hexobarbital,1TBDMS,isomer #1CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O2194.4Standard non polar33892256
Hexobarbital,1TBDMS,isomer #1CN1C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C(C)(C2=CCCCC2)C1=O2736.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Hexobarbital EI-B (Non-derivatized)splash10-00gi-9420000000-001b8f1462933b4fb9c12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hexobarbital EI-B (Non-derivatized)splash10-00gi-9420000000-001b8f1462933b4fb9c12018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexobarbital GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-3940000000-827e61b1deec4916f5792017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexobarbital GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexobarbital GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-05cu-9310000000-eeec363075c613d356962014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 10V, Positive-QTOFsplash10-000i-1190000000-58f9b3cb0025cd8911aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 20V, Positive-QTOFsplash10-014i-2920000000-e4d6ce12b6d33fff56d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 40V, Positive-QTOFsplash10-0uxu-9100000000-55244be11c0d8667c4132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 10V, Negative-QTOFsplash10-000f-7980000000-db4b09996693417c3e092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 20V, Negative-QTOFsplash10-0bt9-5900000000-3fac68a4cc2e19e260872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 40V, Negative-QTOFsplash10-0006-9200000000-8495751984d2901a88262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 10V, Positive-QTOFsplash10-000i-0390000000-d08c51477abaf85bbfa52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 20V, Positive-QTOFsplash10-0a4i-1930000000-cc97a14668452a4e91e12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 40V, Positive-QTOFsplash10-0a4i-6900000000-3951ea29d6dcc2dca21b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 10V, Negative-QTOFsplash10-000i-3490000000-509890f29192f5ebf0062021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 20V, Negative-QTOFsplash10-0a4l-5970000000-fb452294b839815fbe4b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexobarbital 40V, Negative-QTOFsplash10-000x-9450000000-ae3101e9d97123ad0a932021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01355 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01355 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00016768
Chemspider ID3482
KEGG Compound IDC11723
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHexobarbital
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID5706
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1399301
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 ]