FComEx: Dihydrouracil (PC000368)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:15 UTC

Update date

2017-01-19 02:36:21 UTC

FoodComEx ID

PC000368

FoodDB Record

FDB021890

Chemical Information

Name

Dihydrouracil

Description

Dihydrouracil 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. Dihydrouracil is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydrouracil exists in all living organisms, ranging from bacteria to humans. Within humans, dihydrouracil participates in a number of enzymatic reactions. In particular, dihydrouracil can be biosynthesized from uracil; which is mediated by the enzyme dihydropyrimidine dehydrogenase [nadp(+)]. In addition, dihydrouracil can be converted into ureidopropionic acid; which is mediated by the enzyme dihydropyrimidinase. In humans, dihydrouracil is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Outside of the human body, Dihydrouracil has been detected, but not quantified in, several different foods, such as arctic blackberries, garden tomato (var.), sweet potato, star fruits, and adzuki beans. This could make dihydrouracil a potential biomarker for the consumption of these foods. Dihydrouracil is a potentially toxic compound. Dihydrouracil, with regard to humans, has been found to be associated with several diseases such as cerebral infarction, liver disease, colorectal cancer, and hypertension; dihydrouracil has also been linked to the inborn metabolic disorder dihydropyrimidine dehydrogenase deficiency. A pyrimidine obtained by formal addition of hydrogen across the 5,6-position of uracil.

CAS Number

504-07-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2,4-Dioxotetrahydropyrimidine	ChEBI
5,6-Dihydro-2,4-dihydroxypyrimidine	hmdb
5,6-Dihydro-2,4(1H,3H)-pyrimidinedione	hmdb
5,6-Dihydrouracil	hmdb
Dihydro-2,4(1H,3H)-pyrimidinedione	hmdb
Dihydro-pyrimidine-2,4-dione	hmdb
DIHYDROPYRIMIDINE-2,4(1H,3H)-dione	ChEBI
Dihydrouracil	hmdb
Dihydrouracile	hmdb
Hydrouracil	hmdb

Chemical Formula

C4H6N2O2

IUPAC name

1,3-diazinane-2,4-dione

InChI Identifier

InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)

InChI Key

OIVLITBTBDPEFK-UHFFFAOYSA-N

Isomeric SMILES

O=C1CCNC(=O)N1

Average Molecular Weight

114.1026

Monoisotopic Molecular Weight

114.042927446

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