FComEx: Deoxyuridine (PC000141)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:47 UTC

Update date

2017-01-19 02:36:14 UTC

FoodComEx ID

PC000141

FoodDB Record

FDB021870

Chemical Information

Name

Deoxyuridine

Description

Deoxyuridine, also known as dU, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxyuridine is an extremely weak basic (essentially neutral) compound (based on its pKa). Deoxyuridine exists in all living organisms, ranging from bacteria to humans. Within humans, deoxyuridine participates in a number of enzymatic reactions. In particular, deoxyuridine can be biosynthesized from deoxycytidine through its interaction with the enzyme cytidine deaminase. In addition, deoxyuridine can be converted into uracil and deoxyribose 1-phosphate through its interaction with the enzyme thymidine phosphorylase. In humans, deoxyuridine is involved in the metabolic disorder called ump synthase deficiency (orotic aciduria). Outside of the human body, Deoxyuridine is found, on average, in the highest concentration within beers. Deoxyuridine has also been detected, but not quantified in, several different foods, such as cornmints, globe artichokes, lotus, conchs, and lambsquarters. This could make deoxyuridine a potential biomarker for the consumption of these foods. Deoxyuridine is a potentially toxic compound. A pyrimidine 2'-deoxyribonucleoside having uracil as the nucleobase.

CAS Number

951-78-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-(2-deoxy-beta-D-erythro-pentofuranosyl)-2,4(1H,3H)-Pyrimidinedione	hmdb
1-(2-deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-Pyrimidinedione	hmdb
1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-2,4(1H,3H)-Pyrimidinedione	hmdb
1-(2-deoxy-beta-delta-ribofuranosyl)-2,4(1H,3H)-Pyrimidinedione	hmdb
1-(2-Deoxy-D-erythro-pentofuranosyl)uracil	hmdb
1-(2-Deoxy-delta-erythro-pentofuranosyl)uracil	hmdb
2-Deoxyuridine	ChEBI
2'-Deoxyuridine	hmdb
2'-Desoxyuridine	hmdb
Deoxyribose uracil	hmdb
Desoxyuridine	hmdb
Uracil deoxyriboside	hmdb
Uracil desoxyuridine	hmdb

Chemical Formula

C9H12N2O5

IUPAC name

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

InChI Identifier

InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1

InChI Key

MXHRCPNRJAMMIM-SHYZEUOFSA-N

Isomeric SMILES

OC[C@H]1O[C@H](C[C@@H]1O)N1C=CC(=O)NC1=O

Average Molecular Weight

228.202

Monoisotopic Molecular Weight

228.074621504

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents