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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:41:46 UTC
Update Date2019-07-23 06:35:07 UTC
HMDB IDHMDB0041833
Secondary Accession Numbers
  • HMDB41833
Metabolite Identification
Common NameBarbituric acid
DescriptionBarbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid itself is not pharmacologically active. The compound was discovered by the German chemist Adolf von Baeyer on December 4, 1864, the feast of Saint Barbara (who gave the compound its namesake), by combining urea and malonic acid in a condensation reaction. Malonic acid has since been replaced by diethyl malonate, as using the ester avoids the problem of having to deal with the acidity of the carboxylic acid and its unreactive carboxylate.
Structure
Data?1563863707
Synonyms
ValueSource
2,4,6(1H,3H,5H)-PyrimidinetrioneChEBI
BarbitursaeureChEBI
MalonylharnstoffChEBI
MalonylureaChEBI
BarbitateGenerator
Barbitic acidGenerator
2,4,6(1H,3H,5H)-Pyrimidinetrione (acd/name 4.0)HMDB
2,4,6-(1H,3H,5H)-PyrimidinetrioneHMDB
2,4,6-PyrimidinetriolHMDB
2,4,6-Pyrimidinetrione(1H,3H,5H)HMDB
2,4,6-TrihydroxypyrimidineHMDB
2,4,6-TrioxohexahydropyrimidineHMDB
6-HydroxyuracilHMDB
BarbiturateHMDB
BarbitursaureHMDB
N,N'-(1,3-dioxo-1,3-propanediyl)-ureaHMDB
NN'-(1,3-Dioxo-1,3-propanediyl)-ureaHMDB
Pyrimidine-2,4,6(1H,3H,5H)-trioneHMDB
PyrimidinetrioneHMDB
Barbituric acid, monosodium saltHMDB
Sodium barbiturateHMDB
Chemical FormulaC4H4N2O3
Average Molecular Weight128.0862
Monoisotopic Molecular Weight128.022192004
IUPAC Name4,6-dihydroxy-2,5-dihydropyrimidin-2-one
Traditional Namebarbituric acid
CAS Registry Number67-52-7
SMILES
OC1=NC(=O)N=C(O)C1
InChI Identifier
InChI=1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
InChI KeyHNYOPLTXPVRDBG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
Alternative Parents
Substituents
  • Pyrimidone
  • Hydropyrimidine
  • 2,5-dihydropyrimidine
  • Carbonic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point248 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.9e-05 mg/mL at 37 °CNot Available
LogP-1.47Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.04 g/LALOGPS
logP-0.61ALOGPS
logP-0.54ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)5.45ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area82.25 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.62 m³·mol⁻¹ChemAxon
Polarizability10.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001j-4926000000-96492cf12ddafb9fa2c1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9500000000-e1223bb8d4414dc44ce0Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001j-4926000000-96492cf12ddafb9fa2c1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004u-9400000000-0974c3ea74bd38c34f76Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-7960000000-6fe630c5f061865ad590Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-7f6de7dbc0c8385a4986Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-488d5e5740b2d9154278Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-c1265888f45e8b1ed0b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-6900000000-491964469e34c8b797d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-6bad946cb9132732634eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b2a8b5aa5f0c3f979744Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5976
KEGG Compound IDC00813
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBarbituric_acid
METLIN IDNot Available
PubChem Compound6211
PDB IDNot Available
ChEBI ID16294
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available