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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 02:36:51 UTC
Update Date2022-09-22 17:44:21 UTC
HMDB IDHMDB0248870
Secondary Accession NumbersNone
Metabolite Identification
Common NameBarbital
DescriptionBarbital, also known as barbitone or DEBA, 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. Based on a literature review a significant number of articles have been published on Barbital. This compound has been identified in human blood as reported by (PMID: 31557052 ). Barbital is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Barbital is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
2,4,6(1H,3H,5H)-PyrimidinetrioneChEBI
5,5-Diethyl-pyrimidine-2,4,6-trioneChEBI
5,5-Diethylpyrimidine-2,4,6(1H,3H,5H)-trioneChEBI
BarbitoneChEBI
DEBAChEBI
Diethylmalonyl ureaChEBI
VeronalChEBI
DiemalHMDB
MedinalHMDB
EthylbarbitalHMDB
DiethylmalonylureaHMDB
DormilenoHMDB
Barbital faes brandHMDB
Faes brand OF barbitalHMDB
5,5-DiethylbarbitateHMDB
5,5-Diethylbarbitic acidHMDB
BarbitalChEBI
Chemical FormulaC8H12N2O3
Average Molecular Weight184.1925
Monoisotopic Molecular Weight184.08479226
IUPAC Name5,5-diethyl-1,3-diazinane-2,4,6-trione
Traditional Namebarbital
CAS Registry NumberNot Available
SMILES
CCC1(CC)C(=O)NC(=O)NC1=O
InChI Identifier
InChI=1S/C8H12N2O3/c1-3-8(4-2)5(11)9-7(13)10-6(8)12/h3-4H2,1-2H3,(H2,9,10,11,12,13)
InChI KeyFTOAOBMCPZCFFF-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
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.73ALOGPS
logP0.72ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.25 m³·mol⁻¹ChemAxon
Polarizability17.59 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
DeepCCS[M+H]+136.57730932474
DeepCCS[M-H]-132.74530932474
DeepCCS[M-2H]-170.3630932474
DeepCCS[M+Na]+145.930932474
AllCCS[M+H]+140.332859911
AllCCS[M+H-H2O]+136.132859911
AllCCS[M+NH4]+144.232859911
AllCCS[M+Na]+145.432859911
AllCCS[M-H]-139.332859911
AllCCS[M+Na-2H]-140.332859911
AllCCS[M+HCOO]-141.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BarbitalCCC1(CC)C(=O)NC(=O)NC1=O2979.5Standard polar33892256
BarbitalCCC1(CC)C(=O)NC(=O)NC1=O1598.3Standard non polar33892256
BarbitalCCC1(CC)C(=O)NC(=O)NC1=O1457.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Barbital,1TMS,isomer #1CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O1521.8Semi standard non polar33892256
Barbital,1TMS,isomer #1CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O1670.3Standard non polar33892256
Barbital,1TMS,isomer #1CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O2599.6Standard polar33892256
Barbital,2TMS,isomer #1CCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1508.2Semi standard non polar33892256
Barbital,2TMS,isomer #1CCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1725.2Standard non polar33892256
Barbital,2TMS,isomer #1CCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O2128.0Standard polar33892256
Barbital,1TBDMS,isomer #1CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O1754.5Semi standard non polar33892256
Barbital,1TBDMS,isomer #1CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O1909.5Standard non polar33892256
Barbital,1TBDMS,isomer #1CCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2661.2Standard polar33892256
Barbital,2TBDMS,isomer #1CCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O1937.1Semi standard non polar33892256
Barbital,2TBDMS,isomer #1CCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2185.4Standard non polar33892256
Barbital,2TBDMS,isomer #1CCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2277.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Barbital CI-B (Non-derivatized)splash10-000i-0900000000-90fb45d882d2c3ed038f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Barbital EI-B (Non-derivatized)splash10-052f-9400000000-fa1289872f9f35015abc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Barbital EI-B (Non-derivatized)splash10-052f-9500000000-856a7fe5dbfd28d00c382017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Barbital EI-B (Non-derivatized)splash10-0a4l-2900000000-42c0874d0bac13cc2d942017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Barbital EI-B (Non-derivatized)splash10-0a4u-5900000000-497f9ee367181a6df30a2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Barbital GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-5900000000-3c6687662491f8ac6aee2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Barbital 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 - Barbital 10V, Positive-QTOFsplash10-000i-0900000000-c495e9edac16920b65b42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Barbital 20V, Positive-QTOFsplash10-03di-7900000000-627b3602d7bf9ff969132016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Barbital 40V, Positive-QTOFsplash10-01bc-9000000000-d5dcaa6c067db49670292016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Barbital 10V, Negative-QTOFsplash10-000x-5900000000-f428d3f140303ddec9f72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Barbital 20V, Negative-QTOFsplash10-0006-9500000000-d71d709919480c7a3bc32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Barbital 40V, Negative-QTOFsplash10-000x-9200000000-52b1e79e0c2b3207d3bd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Barbital 10V, Positive-QTOFsplash10-000i-0900000000-8f066f6c9186aa8a423c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Barbital 20V, Positive-QTOFsplash10-0a4i-2900000000-79cebb3b5178fd42c3ee2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Barbital 40V, Positive-QTOFsplash10-00r2-9100000000-3dc4615a6b3e3654eeca2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Barbital 10V, Negative-QTOFsplash10-001i-0900000000-3869e238b86b938f0f0e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Barbital 20V, Negative-QTOFsplash10-0006-9300000000-79aafc1759978cac7fa62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Barbital 40V, Negative-QTOFsplash10-0006-9000000000-8313d221f9f4df0b679a2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01483
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00031180
Chemspider ID2206
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBarbital
METLIN IDNot Available
PubChem Compound2294
PDB IDNot Available
ChEBI ID31252
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]