General Information of MET (ID: META00122)
Name Deoxyuridine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(beta 1-(2-Deoxyribopyranosyl))thymidine; 1-(2-Deoxy-D-erythro-pentofuranosyl)uracil; 1-(2-Deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione; 1-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-2,4(1H,3H)-pyrimidinedione; 1-(2-Deoxy-beta-delta-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione; 1-(2-Deoxy-delta-erythro-pentofuranosyl)uracil', 2'-Desoxyuridine, 'Deoxyribose uracil; 2-Deoxyuridine; Deoxyuridine; Desoxyuridine; Uracil deoxyriboside; Uracil desoxyuridine
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;TCM Ingredients;Microbial
Structure Type   Pyrimidine 2'-deoxyribonucleosides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Pyrimidine nucleosides
Pyrimidine 2'-deoxyribonucleosides
PubChem CID
13712
HMDB ID
HMDB0000012
Formula
C9H12N2O5
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=13712"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00526
DrugBank ID
DB02256
ChEBI ID
16450
FooDB ID
FDB021870
ChemSpider ID
13118
METLIN ID
5086
Physicochemical Properties Molecular Weight 228.2 Topological Polar Surface Area 99.1
XlogP -1.6 Complexity 343
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Function
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. It is similar in chemical structure to uridine, but without the 2'-hydroxyl group. 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. Deoxyuridine is considered to be an antimetabolite that is converted into deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemia due to vitamin B12 and folate deficiencies. In humans, deoxyuridine is involved in the metabolic disorder called UMP synthase deficiency (orotic aciduria). Outside of the human body, deoxyuridine has been detected, but not quantified in, several different foods, such as lichee, highbush blueberries, agaves, macadamia nut (M. tetraphylla), and red bell peppers. This could make deoxyuridine a potential biomarker for the consumption of these foods.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Leukotriene-C4 hydrolase (GGT1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockdown (siRNA) of GGT1
                      Induced Change Deoxyuridine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Renal cell carcinoma [ICD-11: 2C90]
                      Details It is reported that knockdown of GGT1 leads to the increase of deoxyuridine levels compared with control group.
      Oxidoreductases (EC 1)
            Glutamate-cysteine ligase modifier (GCLM) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockout of Gclm
                      Induced Change Deoxyuridine concentration: increase (FC = 2.30)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Metabolic liver disease [ICD-11: 5C90]
                      Details It is reported that knockout of Gclm leads to the increase of deoxyuridine levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Knockout of TP53
                      Induced Change Deoxyuridine concentration: increase (Log2 FC=3.23)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of deoxyuridine levels compared with control group.
References
1 Impairment of gamma-glutamyl transferase 1 activity in the metabolic pathogenesis of chromophobe renal cell carcinoma. Proc Natl Acad Sci U S A. 2018 Jul 3;115(27):E6274-E6282.
2 Hepatic metabolic adaptation in a murine model of glutathione deficiency. Chem Biol Interact. 2019 Apr 25;303:1-6.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.