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Record Information
Version1.0
Creation Date2016-07-13 19:43:05 UTC
Update Date2016-08-01 19:10:41 UTC
LmdbLMDB00133
Secondary Accession NumbersNone
Metabolite Identification
Common NameUracil
DescriptionUracil, also known as U or hybar X, 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. Uracil is a drug. Uracil is an extremely weak basic (essentially neutral) compound (based on its pKa). Uracil exists in all living species, ranging from bacteria to humans. Within humans, uracil participates in a number of enzymatic reactions. In particular, uracil and ribose 1-phosphate can be biosynthesized from uridine through the action of the enzyme uridine phosphorylase 2. In addition, uracil can be converted into dihydrouracil through its interaction with the enzyme dihydropyrimidine dehydrogenase [nadp(+)]. In humans, uracil is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. It can also slightly increase the risk for cancer in unusual cases in which the body is extremely deficient in folate. Outside of the human body, uracil has been detected, but not quantified in, several different foods, such as herbs and spices, yams, pasta, carrots, and devilfish. This could make uracil a potential biomarker for the consumption of these foods. Uracil is a potentially toxic compound. Uracil has been found to be associated with several diseases such as crohn's disease, eosinophilic esophagitis, and cerebral infarction; also uracil has been linked to several inborn metabolic disorders including carbamoyl phosphate synthetase deficiency and dihydropyrimidine dehydrogenase deficiency.
Structure
Thumb
Synonyms
ValueSource
2,4(1H,3H)-PyrimidinedioneChEBI
2,4-DioxopyrimidineChEBI
2,4-PyrimidinedioneChEBI
UChEBI
UraChEBI
UrazilChEBI
2,4-DihydroxypyrimidineHMDB
2,4-PyrimidinediolHMDB
Hybar XHMDB
PirodHMDB
PyrodHMDB
Chemical FormulaC4H4N2O2
Average Molecular Weight112.0868
Monoisotopic Molecular Weight112.027277382
IUPAC Name1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Nameuracil
CAS Registry Number66-22-8
SMILES
O=C1NC=CC(=O)N1
InChI Identifier
InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
InChI KeyISAKRJDGNUQOIC-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
  • Heteroaromatic compound
  • Vinylogous amide
  • Urea
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.2ALOGPS
logP-0.86ChemAxon
logS-0.63ALOGPS
pKa (Strongest Acidic)8.8ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.97 m³·mol⁻¹ChemAxon
Polarizability9.37 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-5950000000-18425875415ad150c4fcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006t-9740000000-e884a4b98e7e9dc75e5fSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-052e-7790000000-026cb6beb5cde6a61b80Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-02tc-9200000000-4a57c4e06fd552d6a9bfSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xu-9400000000-1c29f070a8135b06f88bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-5950000000-18425875415ad150c4fcSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-9740000000-e884a4b98e7e9dc75e5fSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-052e-7790000000-026cb6beb5cde6a61b80Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-6940000000-a726178341f6443e60ccSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xu-9300000000-6a96f6ce1ef731689107Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-3900000000-e422eda255a4b6414f86Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006y-9000000000-130eb5f4414426e03667Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-c096d08ca715d97cd732Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-02tc-9200000000-83a0a6ad4fc1b407e570Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03xu-9400000000-acd0cfd54af7d6a55283Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-309fe212c929f3c6a930Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-6900000000-55a7de75a40eab61da8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-1c3caab26eb7e359db92Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-7494d4e611a73ecb79eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-ed4046b040337db620d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0900000000-ff54f3083ce4ccccfd95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-6728c1eb6f68b40c09f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-309fe212c929f3c6a930Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-6900000000-55a7de75a40eab61da8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-1c3caab26eb7e359db92Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-7494d4e611a73ecb79eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-ed4046b040337db620d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-6728c1eb6f68b40c09f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-0900000000-a21102c708f8d5eaf262Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-0029cbdcaa1377a4d03eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-9400000000-c227e1deb392170cb323Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-3cf6f9fc3ab6890266acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4900000000-67a3d94ab649e28bda13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-bbf50de54fc413b6588eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-98042b91f1087b0c2563Spectrum
MSMass Spectrum (Electron Ionization)splash10-03xu-9400000000-d7ffe72f606f1af3349bSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Brain
  • Feces
  • Jejunum
  • Kidney
  • Kidney perfusate
  • Liver
  • Milk
  • Plasma
  • Ruminal Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
BrainDetected but not QuantifiedNot ApplicableNot AvailableOvine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
JejunumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
KidneyDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
Kidney perfusateDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LiverDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Ruminal FluidDetected and Quantified234.6 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified270.2 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified92.6 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified149 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified193 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified224 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified104 +/- 25 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified104 +/- 25 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified121 +/- 40 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified122 +/- 127 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified199 +/- 91 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified246 +/- 48 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified113.2 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified142.5 uMNot AvailableBovine details
DrugBank IDDB03419
HMDB IDHMDB0000300
FooDB IDFDB006426
Phenol Explorer IDNot Available
KNApSAcK IDC00001513
BiGG ID33879
BioCyc IDURACIL
METLIN ID258
PDB IDNot Available
Wikipedia LinkUracil
Chemspider ID1141
ChEBI ID17568
PubChem Compound ID1174
Kegg Compound IDC00106
YMDB IDYMDB00098
ECMDB IDECMDB00300
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available