Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:36 UTC
HMDB IDHMDB0014386
Secondary Accession Numbers
  • HMDB14386
Metabolite Identification
Common NameButalbital
DescriptionButalbital, also known as allylbarbital or itobarbital, 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. Pain perception and reaction are relatively unimpaired until the moment of unconsciousness . Butalbital is a very weakly acidic compound (based on its pKa). In humans, butalbital is involved in acetaminophen action pathway. Butalbital is a short to intermediate-acting barbiturate that reversibly depresses the activity of excitable tissues, including the central nervous system in a nonselective manner . Butalbital is a potentially toxic compound. Additionally, barbiturates promote benzodiazepine binding to the receptor .
Structure
Data?1582753173
Synonyms
ValueSource
5-(2-Methylpropyl)-5-prop-2-enyl-1,3-diazinane-2,4,6-trioneChEBI
5-Allyl-5-(2'-methyl-N-propyl) barbituric acidChEBI
5-Allyl-5-(2-methylpropyl)barbituric acidChEBI
5-Allyl-5-isobutyl-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-Allyl-5-isobutyl-pyrimidine-2,4,6-trioneChEBI
5-Allyl-5-isobutylbarbituric acidChEBI
5-Isobutyl-5-allylbarbituric acidChEBI
AllylbarbitalChEBI
AllylbarbitoneChEBI
Allylbarbituric acidChEBI
ButalbarbitalChEBI
ButalbitalumChEBI
Iso-butylallylbarbituric acidChEBI
ItobarbitalChEBI
TetrallobarbitalChEBI
SandoptalKegg
5-Allyl-5-(2'-methyl-N-propyl) barbitateGenerator
5-Allyl-5-(2'-methyl-N-propyl) barbitic acidGenerator
5-Allyl-5-(2-methylpropyl)barbitateGenerator
5-Allyl-5-(2-methylpropyl)barbitic acidGenerator
5-Allyl-5-isobutylbarbitateGenerator
5-Allyl-5-isobutylbarbitic acidGenerator
5-Isobutyl-5-allylbarbitateGenerator
5-Isobutyl-5-allylbarbitic acidGenerator
AllylbarbitateGenerator
Allylbarbitic acidGenerator
Iso-butylallylbarbitateGenerator
Iso-butylallylbarbitic acidGenerator
Butalbital m (OH)HMDB
Butalbital, monosodium saltHMDB
Chemical FormulaC11H16N2O3
Average Molecular Weight224.2563
Monoisotopic Molecular Weight224.116092388
IUPAC Name5-(2-methylpropyl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
Traditional Namebutalbital
CAS Registry Number77-26-9
SMILES
CC(C)CC1(CC=C)C(=O)NC(=O)NC1=O
InChI Identifier
InChI=1S/C11H16N2O3/c1-4-5-11(6-7(2)3)8(14)12-10(16)13-9(11)15/h4,7H,1,5-6H2,2-3H3,(H2,12,13,14,15,16)
InChI KeyUZVHFVZFNXBMQJ-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 Point138 - 139 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.23 g/LNot Available
LogP1.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.23 g/LALOGPS
logP1.47ALOGPS
logP1.59ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity58.05 m³·mol⁻¹ChemAxon
Polarizability22.42 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]+154.86631661259
DarkChem[M-H]-149.30731661259
DeepCCS[M+H]+148.05230932474
DeepCCS[M-H]-145.69430932474
DeepCCS[M-2H]-180.80330932474
DeepCCS[M+Na]+155.96730932474
AllCCS[M+H]+150.332859911
AllCCS[M+H-H2O]+146.532859911
AllCCS[M+NH4]+153.932859911
AllCCS[M+Na]+154.932859911
AllCCS[M-H]-151.932859911
AllCCS[M+Na-2H]-152.532859911
AllCCS[M+HCOO]-153.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ButalbitalCC(C)CC1(CC=C)C(=O)NC(=O)NC1=O2979.9Standard polar33892256
ButalbitalCC(C)CC1(CC=C)C(=O)NC(=O)NC1=O1641.7Standard non polar33892256
ButalbitalCC(C)CC1(CC=C)C(=O)NC(=O)NC1=O1668.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Butalbital,1TMS,isomer #1C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O1699.7Semi standard non polar33892256
Butalbital,1TMS,isomer #1C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O1834.2Standard non polar33892256
Butalbital,1TMS,isomer #1C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O2819.1Standard polar33892256
Butalbital,2TMS,isomer #1C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1653.7Semi standard non polar33892256
Butalbital,2TMS,isomer #1C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1904.1Standard non polar33892256
Butalbital,2TMS,isomer #1C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O2318.1Standard polar33892256
Butalbital,1TBDMS,isomer #1C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O1910.6Semi standard non polar33892256
Butalbital,1TBDMS,isomer #1C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2063.4Standard non polar33892256
Butalbital,1TBDMS,isomer #1C=CCC1(CC(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2853.1Standard polar33892256
Butalbital,2TBDMS,isomer #1C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2110.9Semi standard non polar33892256
Butalbital,2TBDMS,isomer #1C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2334.7Standard non polar33892256
Butalbital,2TBDMS,isomer #1C=CCC1(CC(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2459.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Butalbital CI-B (Non-derivatized)splash10-004i-0090000000-5925121d468ddb9f88902017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butalbital EI-B (Non-derivatized)splash10-014i-3900000000-b4be8a2b661834f34c862017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butalbital CI-B (Non-derivatized)splash10-004i-0090000000-5925121d468ddb9f88902018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Butalbital EI-B (Non-derivatized)splash10-014i-3900000000-b4be8a2b661834f34c862018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butalbital GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5c-9830000000-e4474c63772bab2bfe872017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butalbital GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butalbital GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Butalbital 35V, Negative-QTOFsplash10-0006-9000000000-a165d26c1f13f5705c412021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 10V, Positive-QTOFsplash10-004i-1290000000-f2dc7511b2d84d11dd0c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 20V, Positive-QTOFsplash10-0zfr-1910000000-f30e268eff072d1ec6282016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 40V, Positive-QTOFsplash10-0a4i-9100000000-96e7e029e762cc8032192016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 10V, Negative-QTOFsplash10-007o-6940000000-a7f9140a1d46b7a9a5a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 20V, Negative-QTOFsplash10-0006-9600000000-39e1938d343fd79e34f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 40V, Negative-QTOFsplash10-0006-9600000000-76a87ece42dfd1cb085f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 10V, Positive-QTOFsplash10-00p0-0940000000-5d6d7ca2edd46a5b76c72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 20V, Positive-QTOFsplash10-0006-1900000000-a698640149964e6093ab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 40V, Positive-QTOFsplash10-066u-9600000000-662b3e70c50e5576e5892021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 10V, Negative-QTOFsplash10-00di-1290000000-44f34a10f5bb5b8258722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 20V, Negative-QTOFsplash10-0006-9010000000-485fbaa88d3ae29c60c52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butalbital 40V, Negative-QTOFsplash10-0006-9300000000-e7f893ff43c0207edb032021-09-22Wishart 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 DB00241 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00241 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00241
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2387
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButalbital
METLIN IDNot Available
PubChem Compound2481
PDB IDNot Available
ChEBI ID102524
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. 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 ]
  4. 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 ]
  5. Cutrer FM, Mitsikostas DD, Ayata G, Sanchez del Rio M: Attenuation by butalbital of capsaicin-induced c-fos-like immunoreactivity in trigeminal nucleus caudalis. Headache. 1999 Nov-Dec;39(10):697-704. [PubMed:11279945 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. 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 ]
  8. 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 ]
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 ]