Deoxyuridine triphosphate (ECMDB01191) (M2MDB000290)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:47:13 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:53:49 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Deoxyuridine triphosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Deoxyuridine triphosphate is an intermediate in the metabolism of Pyrimidine. It is a substrate for Inosine triphosphate pyrophosphatase, Uridine-cytidine kinase 1, Nucleoside diphosphate kinase 3, Nucleoside diphosphate kinase B, Nucleoside diphosphate kinase 6, Nucleoside diphosphate kinase homolog 5, Nucleoside diphosphate kinase A and Nucleoside diphosphate kinase 7. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C9H15N2O14P3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 468.1417 Monoisotopic: 467.973612734 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | AHCYMLUZIRLXAA-SHYZEUOFSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C9H15N2O14P3/c12-5-3-8(11-2-1-7(13)10-9(11)14)23-6(5)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,20,21)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 1173-82-6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | ({[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | dUTP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. These are pyrimidine nucleotides with a triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Pyrimidine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Pyrimidine deoxyribonucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Pyrimidine 2'-deoxyribonucleoside triphosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aromatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | 2 Flavodoxin reduced + 2 Hydrogen ion + Uridine triphosphate > Deoxyuridine triphosphate +2 flavodoxin semi oxidized + Water Adenosine triphosphate + dUDP <> ADP + Deoxyuridine triphosphate Deoxyuridine triphosphate + Water <> dUMP + Hydrogen ion + Pyrophosphate dCTP + Hydrogen ion + Water > Deoxyuridine triphosphate + Ammonium Deoxyuridine triphosphate + Thioredoxin disulfide + Water <> Uridine triphosphate + Thioredoxin Deoxyuridine triphosphate + Water <> dUMP + Pyrophosphate dCTP + Water <> Deoxyuridine triphosphate + Ammonia Adenosine triphosphate + dUDP <> ADP + Deoxyuridine triphosphate Deoxyuridine triphosphate + Uridine <> dUDP + Uridine 5'-monophosphate Deoxyuridine triphosphate + Cytidine <> dUDP + Cytidine monophosphate Water + dCTP > Ammonia + Deoxyuridine triphosphate dUDP + Adenosine triphosphate > Deoxyuridine triphosphate + ADP Deoxyuridine triphosphate + Water > Hydrogen ion + dUMP + Pyrophosphate Deoxyuridine triphosphate + Water > dUMP + Pyrophosphate dUDP + Adenosine triphosphate + dUDP > Adenosine diphosphate + Deoxyuridine triphosphate + ADP Uridine triphosphate + a reduced flavodoxin + Uridine triphosphate > Water + an oxidized flavodoxin + Deoxyuridine triphosphate Deoxyuridine triphosphate + Water > Phosphate + Hydrogen ion + dUMP Deoxyuridine triphosphate + Water <> dUMP + Hydrogen ion + Pyrophosphate Deoxyuridine triphosphate + Water <> dUMP + Hydrogen ion + Pyrophosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in hydrolase activity
- Specific function:
- This enzyme is involved in nucleotide metabolism:it produces dUMP, the immediate precursor of thymidine nucleotides and it decreases the intracellular concentration of dUTP so that uracil cannot be incorporated into DNA
- Gene Name:
- dut
- Uniprot ID:
- P06968
- Molecular weight:
- 16155
Reactions
dUTP + H(2)O = dUMP + diphosphate. |
- General function:
- Involved in nucleoside diphosphate kinase activity
- Specific function:
- Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate
- Gene Name:
- ndk
- Uniprot ID:
- P0A763
- Molecular weight:
- 15463
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate. |
- General function:
- Involved in ATP binding
- Specific function:
- ATP + uridine = ADP + UMP
- Gene Name:
- udk
- Uniprot ID:
- P0A8F4
- Molecular weight:
- 24353
Reactions
ATP + uridine = ADP + UMP. |
ATP + cytidine = ADP + CMP. |
- General function:
- Involved in [formate-C-acetyltransferase]-activating enzyme activity
- Specific function:
- Activation of anaerobic ribonucleoside-triphosphate reductase under anaerobic conditions by generation of an organic free radical, using S-adenosylmethionine and reduced flavodoxin as cosubstrates to produce 5'-deoxy-adenosine
- Gene Name:
- nrdG
- Uniprot ID:
- P0A9N8
- Molecular weight:
- 17446
- General function:
- Involved in nucleoside-triphosphate diphosphatase activity
- Specific function:
- Specific function unknown
- Gene Name:
- mazG
- Uniprot ID:
- P0AEY3
- Molecular weight:
- 30412
Reactions
ATP + H(2)O = AMP + diphosphate. |
- General function:
- Involved in dCTP deaminase activity
- Specific function:
- dCTP + H(2)O = dUTP + NH(3)
- Gene Name:
- dcd
- Uniprot ID:
- P28248
- Molecular weight:
- 21249
Reactions
dCTP + H(2)O = dUTP + NH(3). |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Transports electrons between flavodoxin or ferredoxin and NADPH. Involved in the reductive activation of cobalamin- independent methionine synthase, pyruvate formate lyase and anaerobic ribonucleotide reductase. Also protects against superoxide radicals due to methyl viologen in the presence of oxygen
- Gene Name:
- fpr
- Uniprot ID:
- P28861
- Molecular weight:
- 27751
Reactions
2 reduced ferredoxin + NADP(+) + H(+) = 2 oxidized ferredoxin + NADPH. |
- General function:
- Involved in catalytic activity
- Specific function:
- 2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin
- Gene Name:
- nrdD
- Uniprot ID:
- P28903
- Molecular weight:
- 80022
Reactions
2'-deoxyribonucleoside triphosphate + thioredoxin disulfide + H(2)O = ribonucleoside triphosphate + thioredoxin. |
- General function:
- Involved in hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
- Specific function:
- Catalyzes the hydrolysis of nucleoside triphosphates, with a preference for pyrimidine deoxynucleoside triphosphates (dUTP, dTTP and dCTP)
- Gene Name:
- nudI
- Uniprot ID:
- P52006
- Molecular weight:
- 16371
Reactions
Nucleoside triphosphate + H(2)O = nucleoside monophosphate + diphosphate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Hydrolyzes O6 atom-containing purine bases deoxyinosine triphosphate (dITP) and xanthosine triphosphate (XTP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) to nucleotide monophosphate and pyrophosphate. Probably excludes non- standard purines from DNA precursor pool, preventing thus incorporation into DNA and avoiding chromosomal lesions
- Gene Name:
- rdgB
- Uniprot ID:
- P52061
- Molecular weight:
- 21039
Reactions
A nucleoside triphosphate + H(2)O = a nucleotide + diphosphate. |
- General function:
- Involved in ATP binding
- Specific function:
- Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. This small ubiquitous enzyme involved in the energy metabolism and nucleotide synthesis, is essential for maintenance and cell growth
- Gene Name:
- adk
- Uniprot ID:
- P69441
- Molecular weight:
- 23586
Reactions
ATP + AMP = 2 ADP. |
- General function:
- Involved in FMN binding
- Specific function:
- Low-potential electron donor to a number of redox enzymes (Potential)
- Gene Name:
- fldB
- Uniprot ID:
- P0ABY4
- Molecular weight:
- 19700
- General function:
- Involved in FMN binding
- Specific function:
- Low-potential electron donor to a number of redox enzymes (Potential). Involved in the reactivation of inactive cob(II)alamin in methionine synthase
- Gene Name:
- fldA
- Uniprot ID:
- P61949
- Molecular weight:
- 19737
Transporters
- General function:
- Involved in nucleoside diphosphate kinase activity
- Specific function:
- Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate
- Gene Name:
- ndk
- Uniprot ID:
- P0A763
- Molecular weight:
- 15463
Reactions
ATP + nucleoside diphosphate = ADP + nucleoside triphosphate. |