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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 IDHMDB0015443
Secondary Accession Numbers
  • HMDB15443
Metabolite Identification
Common NameHeptabarbital
DescriptionHeptabarbital is only found in individuals that have used or taken this drug. It is an intermediate or short term barbiturate used mainly for sedation and hypnosis.Heptabarbital (like all barbiturates) works by binding to the GABAA receptor at either the alpha or the beta sub unit. These are binding sites that are distinct from GABA itself and also distinct from the benzodiazepine binding site. Like benzodiazepines, barbiturates potentiate the effect of GABA at this receptor. This GABAA receptor binding decreases input resistance, depresses burst and tonic firing, especially in ventrobasal and intralaminar neurons, while at the same time increasing burst duration and mean conductance at individual chloride channels; this increases both the amplitude and decay time of inhibitory postsynaptic currents. In addition to this GABA-ergic effect, barbiturates also block the AMPA receptor, a subtype of glutamate receptor. Glutamate is the principal excitatory neurotransmitter in the mammalian CNS. Heptabarbital also appears to bind neuronal nicotinic acetylcholine receptors.
Structure
Data?1582753298
Synonyms
ValueSource
HeptabarbHMDB
HeptabarbitoneHMDB
HeptabarbumHMDB
HeptadormHMDB
HeptamalHMDB
HeptamalumHMDB
HeptbarbitalHMDB
MedapanHMDB
MedomineHMDB
Heptabarbital, monosodium saltHMDB
MedominHMDB
Chemical FormulaC13H18N2O3
Average Molecular Weight250.2936
Monoisotopic Molecular Weight250.131742452
IUPAC Name5-(cyclohept-1-en-1-yl)-5-ethyl-1,3-diazinane-2,4,6-trione
Traditional Nameheptabarbital
CAS Registry Number509-86-4
SMILES
CCC1(C(=O)NC(=O)NC1=O)C1=CCCCCC1
InChI Identifier
InChI=1S/C13H18N2O3/c1-2-13(9-7-5-3-4-6-8-9)10(16)14-12(18)15-11(13)17/h7H,2-6,8H2,1H3,(H2,14,15,16,17,18)
InChI KeyPAZQYDJGLKSCSI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives 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
  • N-acyl urea
  • Ureide
  • 1,3-diazinane
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point174 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.32 g/LNot Available
LogP2.03HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP2.41ALOGPS
logP1.91ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)8.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.25 m³·mol⁻¹ChemAxon
Polarizability25.86 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]+158.87631661259
DarkChem[M-H]-155.81431661259
DeepCCS[M+H]+168.3130932474
DeepCCS[M-H]-165.95230932474
DeepCCS[M-2H]-198.83830932474
DeepCCS[M+Na]+174.40330932474
AllCCS[M+H]+158.232859911
AllCCS[M+H-H2O]+154.532859911
AllCCS[M+NH4]+161.732859911
AllCCS[M+Na]+162.732859911
AllCCS[M-H]-160.932859911
AllCCS[M+Na-2H]-160.932859911
AllCCS[M+HCOO]-161.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HeptabarbitalCCC1(C(=O)NC(=O)NC1=O)C1=CCCCCC13432.1Standard polar33892256
HeptabarbitalCCC1(C(=O)NC(=O)NC1=O)C1=CCCCCC12002.6Standard non polar33892256
HeptabarbitalCCC1(C(=O)NC(=O)NC1=O)C1=CCCCCC12059.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Heptabarbital,1TMS,isomer #1CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O2135.6Semi standard non polar33892256
Heptabarbital,1TMS,isomer #1CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O2213.1Standard non polar33892256
Heptabarbital,1TMS,isomer #1CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O3180.9Standard polar33892256
Heptabarbital,2TMS,isomer #1CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O2065.5Semi standard non polar33892256
Heptabarbital,2TMS,isomer #1CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O2240.6Standard non polar33892256
Heptabarbital,2TMS,isomer #1CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O2854.4Standard polar33892256
Heptabarbital,1TBDMS,isomer #1CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2340.1Semi standard non polar33892256
Heptabarbital,1TBDMS,isomer #1CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2441.0Standard non polar33892256
Heptabarbital,1TBDMS,isomer #1CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O3285.0Standard polar33892256
Heptabarbital,2TBDMS,isomer #1CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2479.4Semi standard non polar33892256
Heptabarbital,2TBDMS,isomer #1CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2696.7Standard non polar33892256
Heptabarbital,2TBDMS,isomer #1CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2981.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Heptabarbital CI-B (Non-derivatized)splash10-0udi-0090000000-65df1d705dbf292d19202017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Heptabarbital EI-B (Non-derivatized)splash10-00di-7490000000-252904343000182d024d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Heptabarbital CI-B (Non-derivatized)splash10-0udi-0090000000-65df1d705dbf292d19202018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Heptabarbital EI-B (Non-derivatized)splash10-00di-7490000000-252904343000182d024d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heptabarbital GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-4490000000-f676a100f3d6debe336f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heptabarbital GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 10V, Positive-QTOFsplash10-0udi-1190000000-9cf7406553f0c3090d2b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 20V, Positive-QTOFsplash10-001r-0920000000-354a96c2de9379d61ff72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 40V, Positive-QTOFsplash10-0007-9100000000-b3896ac0c48273f3b1dc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 10V, Negative-QTOFsplash10-052g-6290000000-4db48fb035bc3dc01a832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 20V, Negative-QTOFsplash10-0006-9520000000-b1174b032510d606f67b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 40V, Negative-QTOFsplash10-000x-9500000000-a779572754d9ebabf8492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 10V, Positive-QTOFsplash10-0udi-0090000000-6837e1e1e3c9db8cb8282021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 20V, Positive-QTOFsplash10-000j-3920000000-5838db34fbb1cb18a9572021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 40V, Positive-QTOFsplash10-0a4s-6910000000-ef411a5f84c216e4a3892021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 10V, Negative-QTOFsplash10-002o-6940000000-86c999fda1134290fded2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 20V, Negative-QTOFsplash10-0006-9210000000-9694a6b9a7cdd874a66a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heptabarbital 40V, Negative-QTOFsplash10-0006-9400000000-8a3aea06bcf2795addf52021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01354 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01354 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01354
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10081
KEGG Compound IDC17725
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHeptabarb
METLIN IDNot Available
PubChem Compound10518
PDB IDNot Available
ChEBI ID588074
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ionotropic glutamate receptor activity
Specific function:
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. May be involved in the transmission of light information from the retina to the hypothalamus. Modulates cell surface expression of NETO2
Gene Name:
GRIK2
Uniprot ID:
Q13002
Molecular weight:
102582.5
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist
Gene Name:
GRIA2
Uniprot ID:
P42262
Molecular weight:
98820.3
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
References
  1. Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. [PubMed:14579514 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
  3. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  4. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA2
Uniprot ID:
P47869
Molecular weight:
51325.9
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA3
Uniprot ID:
P34903
Molecular weight:
55164.1
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA4
Uniprot ID:
P48169
Molecular weight:
61622.6
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA5
Uniprot ID:
P31644
Molecular weight:
52145.6
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA6
Uniprot ID:
Q16445
Molecular weight:
51023.7
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
  2. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]