FComEx: Uracil (PC000048)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:43 UTC

Update date

2017-01-19 02:36:11 UTC

FoodComEx ID

PC000048

FoodDB Record

FDB006426

Chemical Information

Name

Uracil

Description

Uracil, 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 Number

66-22-8

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
1H-Pyrimidine-2,4-dione	biospider
2,4-dihydroxypyrimidine	biospider
2,4-Dioxopyrimidine	biospider
2,4-Pyrimidinediol	biospider
2,4-Pyrimidinedione	biospider
2,4(1H,3H)-Pyrimidinedione	biospider
2,4(1H,3H)-Pyrimidinedione (9CI)	biospider
Hybar X	HMDB
Pirod	HMDB
Pyrod	biospider
U	ChEBI
Ura	ChEBI
Urazil	biospider

Chemical Formula

C4H4N2O2

IUPAC name

1,2,3,4-tetrahydropyrimidine-2,4-dione

InChI Identifier

InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)

InChI Key

ISAKRJDGNUQOIC-UHFFFAOYSA-N

Isomeric SMILES

O=C1NC=CC(=O)N1

Average Molecular Weight

112.0868

Monoisotopic Molecular Weight

112.027277382

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents