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Record Information
Version1.0
Creation Date2016-09-30 22:28:03 UTC
Update Date2020-06-04 20:52:17 UTC
BMDB IDBMDB0000300
Secondary Accession Numbers
  • BMDB00300
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 exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Uracil exists in all living species, ranging from bacteria to humans. Uracil is a potentially toxic compound.
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 NameNot Available
Traditional NameNot Available
CAS Registry Number66-22-8
SMILESNot Available
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
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point330 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.6 mg/mLNot Available
LogP-1.07HANSCH,C ET AL. (1995)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • All Tissues
  • Liver
  • Mammary Gland
  • Milk
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified76 +/- 30 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified113.18 +/- 24.69 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified142.5 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified234.6 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified270.2 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified113.2 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified1007 +/- 230 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Ruminal FluidDetected and Quantified109-405 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified122 +/- 127 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified199 +/- 91 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified246 +/- 48 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified104 +/- 25 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified104 +/- 25 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified149 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified193 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified224 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified92.6 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Ruminal FluidDetected and Quantified270.19 +/- 43.37 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000300
DrugBank IDDB03419
Phenol Explorer Compound IDNot Available
FooDB IDFDB006426
KNApSAcK IDC00001513
Chemspider ID1141
KEGG Compound IDC00106
BioCyc IDURACIL
BiGG ID33879
Wikipedia LinkUracil
METLIN ID258
PubChem Compound1174
PDB IDNot Available
ChEBI ID17568
References
Synthesis ReferenceBurckhalter, J. H.; Scarborough, Homer C. The synthesis of uracils as anticonvulsants. Journal of the American Pharmaceutical Association (1912-1977) (1955), 44 545-50.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine.
Gene Name:
DPYD
Uniprot ID:
Q28007
Molecular weight:
111697.0
Reactions
Dihydrouracil + NADP → Uracil + NADPHdetails
Uracil + NADP → Dihydrouracil + NADPHdetails
General function:
Nucleotide transport and metabolism
Specific function:
Not Available
Gene Name:
UPRT
Uniprot ID:
Q32LA4
Molecular weight:
33355.0
General function:
Not Available
Specific function:
Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:
UPP2
Uniprot ID:
Q0VCM7
Molecular weight:
35805.0
Reactions
Uridine + Hydrogen phosphate → Uracil + Ribose 1-phosphatedetails