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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 IDHMDB0015441
Secondary Accession Numbers
  • HMDB15441
Metabolite Identification
Common NameAprobarbital
DescriptionAprobarbital, also known as allypropymal or alurate, 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. Aprobarbital is a very weakly acidic compound (based on its pKa). Aprobarbital was never as widely used as more common barbiturate derivatives such as phenobarbital and is now rarely prescribed as it has been replaced by newer drugs with a better safety margin. It has sedative, hypnotic and anticonvulsant properties, and was used primarily for the treatment of insomnia. Aprobarbital (or aprobarbitone), sold as Oramon, Somnifaine, and Allonal, is a barbiturate derivative invented in the 1920s by Ernst Preiswerk.
Structure
Data?1582753298
Synonyms
ValueSource
5-(1-Methylethyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-Allyl-5-isopropylbarbituric acidChEBI
5-Allyl-5-isopropylpyrimidine-2,4,6(1H,3H,5H)-trioneChEBI
5-Isopropyl-5-allylbarbituric acidChEBI
AllypropymalChEBI
AlurateChEBI
5-Allyl-5-isopropylbarbitateGenerator
5-Allyl-5-isopropylbarbitic acidGenerator
5-Isopropyl-5-allylbarbitateGenerator
5-Isopropyl-5-allylbarbitic acidGenerator
Aluric acidGenerator
AlateHMDB
Alic acidHMDB
AllylpropymalHMDB
AprobarbitoneHMDB
Allylpropymal, monosodium saltHMDB
Chemical FormulaC10H14N2O3
Average Molecular Weight210.2298
Monoisotopic Molecular Weight210.100442324
IUPAC Name5-(prop-2-en-1-yl)-5-(propan-2-yl)-1,3-diazinane-2,4,6-trione
Traditional Nameaprobarbital
CAS Registry Number77-02-1
SMILES
CC(C)C1(CC=C)C(=O)NC(=O)NC1=O
InChI Identifier
InChI=1S/C10H14N2O3/c1-4-5-10(6(2)3)7(13)11-9(15)12-8(10)14/h4,6H,1,5H2,2-3H3,(H2,11,12,13,14,15)
InChI KeyUORJNBVJVRLXMQ-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
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point141 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.17 g/LNot Available
LogP1.15HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.17 g/LALOGPS
logP1.24ALOGPS
logP1.14ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.45 m³·mol⁻¹ChemAxon
Polarizability20.5 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]+148.11631661259
DarkChem[M-H]-144.14131661259
DeepCCS[M+H]+147.80730932474
DeepCCS[M-H]-143.97930932474
DeepCCS[M-2H]-181.42730932474
DeepCCS[M+Na]+156.96630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AprobarbitalCC(C)C1(CC=C)C(=O)NC(=O)NC1=O2916.0Standard polar33892256
AprobarbitalCC(C)C1(CC=C)C(=O)NC(=O)NC1=O1605.5Standard non polar33892256
AprobarbitalCC(C)C1(CC=C)C(=O)NC(=O)NC1=O1606.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aprobarbital,1TMS,isomer #1C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O1609.1Semi standard non polar33892256
Aprobarbital,1TMS,isomer #1C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O1763.8Standard non polar33892256
Aprobarbital,1TMS,isomer #1C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O2663.9Standard polar33892256
Aprobarbital,2TMS,isomer #1C=CCC1(C(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1570.6Semi standard non polar33892256
Aprobarbital,2TMS,isomer #1C=CCC1(C(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1820.4Standard non polar33892256
Aprobarbital,2TMS,isomer #1C=CCC1(C(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O2212.2Standard polar33892256
Aprobarbital,1TBDMS,isomer #1C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O1816.5Semi standard non polar33892256
Aprobarbital,1TBDMS,isomer #1C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O1991.8Standard non polar33892256
Aprobarbital,1TBDMS,isomer #1C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2706.9Standard polar33892256
Aprobarbital,2TBDMS,isomer #1C=CCC1(C(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2018.0Semi standard non polar33892256
Aprobarbital,2TBDMS,isomer #1C=CCC1(C(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2251.5Standard non polar33892256
Aprobarbital,2TBDMS,isomer #1C=CCC1(C(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2361.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Aprobarbital EI-B (Non-derivatized)splash10-014l-9600000000-9ab2ab6ff36ccb20312f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Aprobarbital CI-B (Non-derivatized)splash10-03di-0090000000-b13a014a6928d07475672017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Aprobarbital EI-B (Non-derivatized)splash10-014l-9600000000-9ab2ab6ff36ccb20312f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Aprobarbital CI-B (Non-derivatized)splash10-03di-0090000000-b13a014a6928d07475672018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aprobarbital GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-6900000000-8e2fadd8c703abf57cab2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aprobarbital 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 - Aprobarbital 35V, Negative-QTOFsplash10-052g-9340000000-7606e92a526391d4fe692021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 10V, Positive-QTOFsplash10-03di-0390000000-181ed7f48a6f8b2be4592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 20V, Positive-QTOFsplash10-0005-4900000000-c3ed55bedff14b2893f72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 40V, Positive-QTOFsplash10-000x-9000000000-7921b62ac5b52f86c3732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 10V, Negative-QTOFsplash10-05mo-8950000000-b232a6440f5538b1f92e2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 20V, Negative-QTOFsplash10-0006-9500000000-7ed9cf57a53d840954492016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 40V, Negative-QTOFsplash10-0007-9200000000-55c099997913083a521f2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 10V, Positive-QTOFsplash10-03di-0790000000-0080941b73c060d0c3ea2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 20V, Positive-QTOFsplash10-052b-9210000000-bb699f2867a4017b84e12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 40V, Positive-QTOFsplash10-0a4j-9100000000-37fda3df56bd06c65a0a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 10V, Negative-QTOFsplash10-0a4i-2390000000-5fc08243ebac6ecef3e12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 20V, Negative-QTOFsplash10-0006-9100000000-6264c5b2cdaf4d9ea4532021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aprobarbital 40V, Negative-QTOFsplash10-0006-9400000000-6f85e6486e25545f181a2021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 DB01352 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01352 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01352
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6221
KEGG Compound IDC07826
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAprobarbital
METLIN IDNot Available
PubChem Compound6464
PDB IDNot Available
ChEBI ID2791
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 ]