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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 IDHMDB0015442
Secondary Accession Numbers
  • HMDB15442
Metabolite Identification
Common NameButethal
DescriptionButethal is only found in individuals that have used or taken this drug. It is a sedative and a hypnotic drug.Butethal binds at a distinct binding site associated with a Cl- ionopore at the GABAA 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. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.
Structure
Data?1582753298
Synonyms
ValueSource
NeonalKegg
5-Butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrioneHMDB
5-Butyl-5-ethylbarbituric acidHMDB
5-Ethyl-5-butylbarbituric acidHMDB
5-Ethyl-5-N-butylbarbituric acidHMDB
ButabarbitolHMDB
ButobarbitalHMDB
ButobarbitalumHMDB
ButobarbitoneHMDB
ButobarbituralHMDB
Butyl,5-ethylbarbituric acidHMDB
SonerylHMDB
Butethal, monosodium saltHMDB
Butobarbital, sodium saltHMDB
ButethalKEGG
Chemical FormulaC10H16N2O3
Average Molecular Weight212.2456
Monoisotopic Molecular Weight212.116092388
IUPAC Name5-butyl-5-ethyl-1,3-diazinane-2,4,6-trione
Traditional Namebutethal
CAS Registry Number77-28-1
SMILES
CCCCC1(CC)C(=O)NC(=O)NC1=O
InChI Identifier
InChI=1S/C10H16N2O3/c1-3-5-6-10(4-2)7(13)11-9(15)12-8(10)14/h3-6H2,1-2H3,(H2,11,12,13,14,15)
InChI KeySTDBAQMTJLUMFW-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point128.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.27 g/LNot Available
LogP1.73HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.27 g/LALOGPS
logP1.65ALOGPS
logP1.61ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.45 m³·mol⁻¹ChemAxon
Polarizability21.62 ųChemAxon
Number of Rings1ChemAxon
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]+150.03231661259
DarkChem[M-H]-145.88431661259
DeepCCS[M+H]+148.5730932474
DeepCCS[M-H]-144.74130932474
DeepCCS[M-2H]-182.21530932474
DeepCCS[M+Na]+157.75530932474
AllCCS[M+H]+148.632859911
AllCCS[M+H-H2O]+144.632859911
AllCCS[M+NH4]+152.232859911
AllCCS[M+Na]+153.332859911
AllCCS[M-H]-150.032859911
AllCCS[M+Na-2H]-150.632859911
AllCCS[M+HCOO]-151.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ButethalCCCCC1(CC)C(=O)NC(=O)NC1=O3157.7Standard polar33892256
ButethalCCCCC1(CC)C(=O)NC(=O)NC1=O1652.4Standard non polar33892256
ButethalCCCCC1(CC)C(=O)NC(=O)NC1=O1640.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Butethal,1TMS,isomer #1CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O1684.1Semi standard non polar33892256
Butethal,1TMS,isomer #1CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O1829.4Standard non polar33892256
Butethal,1TMS,isomer #1CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O2806.2Standard polar33892256
Butethal,2TMS,isomer #1CCCCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1666.7Semi standard non polar33892256
Butethal,2TMS,isomer #1CCCCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1878.4Standard non polar33892256
Butethal,2TMS,isomer #1CCCCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O2296.0Standard polar33892256
Butethal,1TBDMS,isomer #1CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O1897.4Semi standard non polar33892256
Butethal,1TBDMS,isomer #1CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2063.7Standard non polar33892256
Butethal,1TBDMS,isomer #1CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2843.3Standard polar33892256
Butethal,2TBDMS,isomer #1CCCCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2091.5Semi standard non polar33892256
Butethal,2TBDMS,isomer #1CCCCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2321.0Standard non polar33892256
Butethal,2TBDMS,isomer #1CCCCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2434.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Butethal EI-B (Non-derivatized)splash10-0006-9600000000-eef99ddbb9fc48cf8ed42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butethal CI-B (Non-derivatized)splash10-03di-0090000000-3021b7118b324b8467bd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butethal EI-B (Non-derivatized)splash10-0006-9600000000-eef99ddbb9fc48cf8ed42018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butethal CI-B (Non-derivatized)splash10-03di-0090000000-3021b7118b324b8467bd2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butethal GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ru-8900000000-4af4f13ca7ae2bc7fcda2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butethal 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 - Butethal 10V, Positive-QTOFsplash10-03di-1390000000-43ecd68f229c3c3bc90c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butethal 20V, Positive-QTOFsplash10-0006-4900000000-1b15cbf105e1de8882202016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butethal 40V, Positive-QTOFsplash10-052f-9000000000-205e856802a03c319f4c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butethal 10V, Negative-QTOFsplash10-0296-7940000000-170e8b066d6c58e18ace2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butethal 20V, Negative-QTOFsplash10-0006-9500000000-aa05ed5e0280f5ac92f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butethal 40V, Negative-QTOFsplash10-0006-9500000000-8169dd5585539f0b6ae02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butethal 10V, Positive-QTOFsplash10-0a4i-0920000000-404a31fe18ef594f21df2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butethal 20V, Positive-QTOFsplash10-0a4j-3900000000-e48f90bfca377565c24e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butethal 40V, Positive-QTOFsplash10-0002-9400000000-f5a557249efe744106d52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butethal 10V, Negative-QTOFsplash10-03di-0090000000-39954a7265a9cf3de21b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butethal 20V, Negative-QTOFsplash10-03dl-6090000000-1346133bfd2e9697f1502021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butethal 40V, Negative-QTOFsplash10-0006-9300000000-b5bed8f717a537bd25832021-10-11Wishart 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 DB01353 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01353 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 IDDB01353
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6229
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButobarbital
METLIN IDNot Available
PubChem Compound6473
PDB IDNot Available
ChEBI ID519412
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 ]
  5. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  6. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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 ]