Record Information
Version1.0
Creation date2010-04-08 22:07:08 UTC
Update date2020-09-17 15:38:35 UTC
Primary IDFDB006426
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 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; which is catalyzed by 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 pyrimidine metabolism. Outside of the human body, Uracil is found, on average, in the highest concentration within beers. Uracil has also been detected, but not quantified in, several different foods, such as radish (var.), green beans, cauliflowers, prickly pears, and citrus. This could make uracil a potential biomarker for the consumption of these foods. Uracil is a potentially toxic compound. Uracil, with regard to humans, has been found to be associated with several diseases such as canavan disease, hypertension, and cerebral infarction; uracil has also been linked to several inborn metabolic disorders including carbamoyl phosphate synthetase deficiency and dihydropyrimidine dehydrogenase deficiency.
CAS Number66-22-8
Structure
Thumb
Synonyms
SynonymSource
2,4(1H,3H)-PyrimidinedioneChEBI
2,4-DioxopyrimidineChEBI
2,4-PyrimidinedioneChEBI
UChEBI
UraChEBI
UrazilChEBI
2,4-DihydroxypyrimidineHMDB
2,4-PyrimidinediolHMDB
Hybar XHMDB
PirodHMDB
PyrodHMDB
1H-Pyrimidine-2,4-dionebiospider
2,4-dihydroxypyrimidinebiospider
2,4(1H,3H)-Pyrimidinedione (9CI)biospider
Predicted PropertiesNot Available
Chemical FormulaC4H4N2O2
IUPAC name
InChI IdentifierInChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
InChI KeyISAKRJDGNUQOIC-UHFFFAOYSA-N
Isomeric SMILESO=C1NC=CC(=O)N1
Average Molecular Weight112.0868
Monoisotopic Molecular Weight112.027277382
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point330 oC
Boiling PointNot Available
Experimental Water Solubility3.6 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-1.07HANSCH,C ET AL. (1995)
Experimental pKa9.45
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID1141
ChEMBL IDCHEMBL566
KEGG Compound IDC00106
Pubchem Compound ID1174
Pubchem Substance IDNot Available
ChEBI ID17568
Phenol-Explorer IDNot Available
DrugBank IDDB03419
HMDB IDHMDB00300
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDURACIL
BIGG ID33879
KNApSAcK IDC00001513
HET IDURA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDUracil
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Purine nucleoside phosphorylasePNPP00491
Thymidine phosphorylaseTYMPP19971
Uridine phosphorylase 1UPP1Q16831
Uridine phosphorylase 2UPP2O95045
Uridine-cytidine kinase-like 1UCKL1Q9NWZ5
Uracil phosphoribosyltransferase homologUPRTQ96BW1
Pathways
NameSMPDB LinkKEGG Link
Beta-Alanine MetabolismSMP00007 map00410
Pyrimidine MetabolismSMP00046 map00240
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).