Uridine triphosphate (ECMDB00285) (M2MDB000117)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:25:32 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:53:27 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Uridine triphosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Uridine 5'-(tetrahydrogen triphosphate). A uracil nucleotide containing three phosphate groups esterified to the sugar moiety. Uridine triphosphate has the role of a source of energy or an activator of substrates in metabolic reactions, like that of adenosine triphosphate, but more specific. When Uridine triphosphate activates a substrate, UDP-substrate is usually formed and inorganic phosphate is released. (Wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C9H15N2O15P3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 484.1411 Monoisotopic: 483.968527356 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | PGAVKCOVUIYSFO-XVFCMESISA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C9H15N2O15P3/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 63-39-8 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | ({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | uridine 5'-triphosphoric acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | O[C@H]1[C@@H](O)[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 ribonucleoside triphosphates. These are pyrimidine ribobucleotides with triphosphate group linked to the ribose moiety. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Pyrimidine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Pyrimidine ribonucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Pyrimidine ribonucleoside triphosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents |
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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 + Uridine 5'-diphosphate <> ADP + Uridine triphosphate Glucose 1-phosphate + Hydrogen ion + Uridine triphosphate <> Pyrophosphate + UDP-Glucose Adenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + Phosphate Water + Uridine triphosphate > Hydrogen ion + Pyrophosphate + Uridine 5'-monophosphate N-Acetyl-glucosamine 1-phosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + Uridine diphosphate-N-acetylglucosamine Uridine triphosphate + Glucose 1-phosphate <> Pyrophosphate + UDP-Glucose Uridine triphosphate + Glucosamine-1P <> Pyrophosphate + Uridine diphosphate-N-acetylglucosamine Uridine triphosphate + RNA <> Pyrophosphate + RNA Uridine triphosphate + Cytidine <> Uridine 5'-diphosphate + Cytidine monophosphate Cytidine triphosphate + Water <> Uridine triphosphate + Ammonia Adenosine triphosphate + Uridine triphosphate + Ammonia <> ADP + Phosphate + Cytidine triphosphate Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water <> ADP + Phosphate + Cytidine triphosphate + L-Glutamate Uridine triphosphate + Water <> Uridine 5'-monophosphate + Pyrophosphate Uridine triphosphate + Uridine <> Uridine 5'-diphosphate + Uridine 5'-monophosphate Deoxyuridine triphosphate + Thioredoxin disulfide + Water <> Uridine triphosphate + Thioredoxin Uridine triphosphate + D-Tagatose 6-phosphate <> Uridine 5'-diphosphate + D-Tagatose 1,6-bisphosphate Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water > Hydrogen ion + ADP + Phosphate + Cytidine triphosphate + L-Glutamate Hydrogen ion + Glucose 1-phosphate + Uridine triphosphate > UDP-Glucose + Pyrophosphate Hydrogen ion + <i>N</i>-acetyl-α-D-glucosamine 1-phosphate + Uridine triphosphate > Uridine diphosphate-N-acetylglucosamine + Pyrophosphate Uridine 5'-diphosphate + Adenosine triphosphate > Uridine triphosphate + ADP Uridine triphosphate + Alpha-D-glucose 1-phosphate > Pyrophosphate + UDP-Glucose Uridine triphosphate + N-acetyl-alpha-D-glucosamine 1-phosphate > Pyrophosphate + Uridine diphosphate-N-acetylglucosamine Uridine triphosphate + [protein-PII] > Pyrophosphate + uridylyl-[protein-PII] Adenosine triphosphate + Uridine triphosphate + Ammonia > ADP + Inorganic phosphate + Cytidine triphosphate Adenosine triphosphate + Uridine triphosphate + L-Glutamine + Water + Ammonia <> ADP + Phosphate + Cytidine triphosphate + L-Glutamate More...Uridine triphosphate + [Protein-PII] <> Pyrophosphate + Uridylyl-[protein-PII] Glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + UDP-Glucose β-D-glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > UDP-Glucose + Pyrophosphate Alpha-D-glucose 1-phosphate + Uridine triphosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + UDP-Glucose N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate + Hydrogen ion + N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate > Uridine diphosphate-N-acetylglucosamine + Pyrophosphate Uridine 5'-diphosphate + Adenosine triphosphate + Uridine 5'-diphosphate > Uridine triphosphate + Adenosine diphosphate + Uridine triphosphate + ADP Uridine triphosphate + a reduced flavodoxin + Uridine triphosphate > Water + an oxidized flavodoxin + Deoxyuridine triphosphate Uridine triphosphate + L-Glutamine + Water + Adenosine triphosphate + Uridine triphosphate > Adenosine diphosphate + Hydrogen ion + Phosphate + L-Glutamic acid + Cytidine triphosphate + ADP + L-Glutamate Glucose 1-phosphate + Hydrogen ion + Uridine triphosphate <> Pyrophosphate + UDP-Glucose Uridine triphosphate + Glucose 1-phosphate <> Pyrophosphate + UDP-Glucose Adenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + Phosphate Uridine triphosphate + [Protein-PII] <> Pyrophosphate + Uridylyl-[protein-PII] Adenosine triphosphate + Uridine 5'-diphosphate <> ADP + Uridine triphosphate Uridine triphosphate + Glucosamine-1P <> Pyrophosphate + Uridine diphosphate-N-acetylglucosamine Adenosine triphosphate + L-Glutamine + Water + Uridine triphosphate > ADP + Cytidine triphosphate + L-Glutamate +2 Hydrogen ion + Phosphate Uridine triphosphate + [Protein-PII] <> Pyrophosphate + Uridylyl-[protein-PII] Adenosine triphosphate + Uridine 5'-diphosphate <> ADP + Uridine triphosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Kenner, G. W.; Todd, A. R.; Webb, R. F.; Weymouth, F. J. Nucleotides. XXVIII. Synthesis of uridine 5'-triphosphate. Journal of the Chemical Society (1954), 46-52 2288-93. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in phosphotransferase activity, alcohol group as acceptor
- Specific function:
- ATP + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
- Gene Name:
- pfkB
- Uniprot ID:
- P06999
- Molecular weight:
- 32456
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate. |
- 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 + D-fructose 6-phosphate = ADP + D- fructose 1,6-bisphosphate
- Gene Name:
- pfkA
- Uniprot ID:
- P0A796
- Molecular weight:
- 34842
Reactions
ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate. |
- General function:
- Involved in CTP synthase activity
- Specific function:
- Catalyzes the ATP-dependent amination of UTP to CTP with either L-glutamine or ammonia as the source of nitrogen
- Gene Name:
- pyrG
- Uniprot ID:
- P0A7E5
- Molecular weight:
- 60374
Reactions
ATP + UTP + NH(3) = ADP + phosphate + CTP. |
- General function:
- Involved in DNA-directed RNA polymerase activity
- Specific function:
- DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates. This subunit plays an important role in subunit assembly since its dimerization is the first step in the sequential assembly of subunits to form the holoenzyme
- Gene Name:
- rpoA
- Uniprot ID:
- P0A7Z4
- Molecular weight:
- 36511
Reactions
Nucleoside triphosphate + RNA(n) = diphosphate + RNA(n+1). |
- General function:
- Involved in DNA-directed RNA polymerase activity
- Specific function:
- Promotes RNA polymerase assembly. Latches the N- and C- terminal regions of the beta' subunit thereby facilitating its interaction with the beta and alpha subunits
- Gene Name:
- rpoZ
- Uniprot ID:
- P0A800
- Molecular weight:
- 10237
Reactions
Nucleoside triphosphate + RNA(n) = diphosphate + RNA(n+1). |
- 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 DNA binding
- Specific function:
- DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates
- Gene Name:
- rpoC
- Uniprot ID:
- P0A8T7
- Molecular weight:
- 155159
Reactions
Nucleoside triphosphate + RNA(n) = diphosphate + RNA(n+1). |
- General function:
- Involved in DNA binding
- Specific function:
- DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates
- Gene Name:
- rpoB
- Uniprot ID:
- P0A8V2
- Molecular weight:
- 150631
Reactions
Nucleoside triphosphate + RNA(n) = diphosphate + RNA(n+1). |
- 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 enzyme regulator activity
- Specific function:
- UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose
- Gene Name:
- galF
- Uniprot ID:
- P0AAB6
- Molecular weight:
- 32829
Reactions
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- Catalyzes the last two sequential reactions in the de novo biosynthetic pathway for UDP-GlcNAc. Responsible for the acetylation of Glc-N-1-P to give GlcNAc-1-P and for the uridyl transfer from UTP to GlcNAc-1-P which produces UDP-GlcNAc
- Gene Name:
- glmU
- Uniprot ID:
- P0ACC7
- Molecular weight:
- 49190
Reactions
Acetyl-CoA + alpha-D-glucosamine 1-phosphate = CoA + N-acetyl-alpha-D-glucosamine 1-phosphate. |
UTP + N-acetyl-alpha-D-glucosamine 1-phosphate = diphosphate + UDP-N-acetyl-D-glucosamine. |
- General function:
- Involved in UTP:glucose-1-phosphate uridylyltransferase activity
- Specific function:
- May play a role in stationary phase survival
- Gene Name:
- galU
- Uniprot ID:
- P0AEP3
- Molecular weight:
- 32942
Reactions
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose. |
- 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 amino acid binding
- Specific function:
- Modifies, by uridylylation or deuridylylation the PII (glnB) regulatory protein
- Gene Name:
- glnD
- Uniprot ID:
- P27249
- Molecular weight:
- 102389
Reactions
UTP + [protein-PII] = diphosphate + uridylyl-[protein-PII]. |
- 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
- 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. |