General Information of MET (ID: META00386)
Name dUTP
Synonyms   Click to Show/Hide Synonyms of This Metabolite
2'-Deoxyuridine 5'-triphosphate, 2'-Deoxyuridine 5'-triphosphoric acid, 'Deoxyuridine triphosphoric acid', 2'-Deoxyuridine-5'-triphosphorate, 2'-Deoxyuridine-5'-triphosphoric acid, 2'-Deoxyuridine-5'-triphosphoric acid = dUTP, 'Deoxy-UTP', Deoxyuridine-5'-triphosphate, 'dUTP
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Toxins/Pollutant;Microbial
Structure Type   Pyrimidine deoxyribonucleotides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Pyrimidine nucleotides
Pyrimidine deoxyribonucleotides
PubChem CID
65070
HMDB ID
HMDB0001191
Formula
C9H15N2O14P3
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00460
DrugBank ID
DB02333
ChEBI ID
17625
FooDB ID
FDB022478
ChemSpider ID
58580
METLIN ID
6069
Physicochemical Properties Molecular Weight 468.14 Topological Polar Surface Area 239
XlogP -5.5 Complexity 808
Heavy Atom Count 28 Rotatable Bond Count 8
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 14
Function
Deoxyuridine triphosphate (dUTP) is a deoxynucleotide triphosphate (dNTP) that is chemically similar to uridine triphosphate (UTP) except that it has a deoxyribose sugar instead of a ribose sugar. DNA synthesis requires the availability of deoxynucleotide triphosphates (dTTP, dATP, dGTP, dCTP), whereas RNA synthesis requires the availability of nucleotide triphosphates (NTPs) such as TTP, ATP, GTP, and UTP. The conversion of nucleotide triphosphates (NTPs) into dNTPs can only be done in the diphosphate form. Typically, an NTP has one phosphate removed to become an NDP. This is then converted into a dNDP by an enzyme called ribonucleotide reductase and followed by the re-addition of phosphate to give a dNTP. dUTP is a substrate for several enzymes, including inosine triphosphate pyrophosphatase, deoxyuridine 5'-triphosphate nucleotidohydrolase (mitochondrial), uridine-cytidine kinase 1, nucleoside diphosphate kinase 3, nucleoside diphosphate kinase B, nucleoside diphosphate kinase 6, nucleoside diphosphate kinase (mitochondrial), nucleoside diphosphate kinase homolog 5, nucleoside diphosphate kinase A, and nucleoside diphosphate kinase 7. While UTP is routinely incorporated into RNA, dUTP is not normally incorporated into DNA. Instead, if dUTP is misincorporated into DNA, it can cause DNA damage. Therefore, dUTP can be considered as a teratogen or a mutagen. The extent of DNA damage caused by dUTP is highly dependent on the levels of the dUTP pyrophosphatase (dUTPase) and uracil-DNA glycosylase (UDG), which limits the intracellular accumulation of dUTP. Additionally, loss of viability following thymidylate synthase (TS) inhibition occurs as a consequence of the accumulation of dUTP in some cell lines and subsequent misincorporation of uracil into DNA.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      GPCR secretin (GPCR-2)
            Glucagon receptor (GCGR) 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 Knockout of Gcgr
                      Induced Change dUTP concentration: decrease (FC = 1.3)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Type 2 diabetes mellitus [ICD-11: 5A11]
                      Details It is reported that knockout of GCGR leads to the decrease of dUTP levels compared with control group.
      Mitochondrial carrier (MC)
            Solute carrier family 25 member 33 (SLC25A33) 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 Recombinant protein addition of SLC25A33
                      Induced Change dUTP concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that recombinant protein addition of SLC25A33 leads to the increase of dUTP levels compared with control group.
            Solute carrier family 25 member 36 (SLC25A36) 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 Recombinant protein addition of SLC25A36
                      Induced Change dUTP concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that recombinant protein addition of SLC25A36 leads to the increase of dUTP levels compared with control group.
References
1 Polyomic profiling reveals significant hepatic metabolic alterations in glucagon-receptor (GCGR) knockout mice: implications on anti-glucagon therapies for diabetes. BMC Genomics. 2011 Jun 1;12:281.
2 The human SLC25A33 and SLC25A36 genes of solute carrier family 25 encode two mitochondrial pyrimidine nucleotide transporters. J Biol Chem. 2014 Nov 28;289(48):33137-48.

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