dCTP (ECMDB00998) (M2MDB000219)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:03:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:53:39 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | dCTP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Deoxycytidine triphosphate (dCTP) is a cytidine nucleotide triphosphate that is used whenever DNA is synthesized, such as in the polymerase chain reaction. e.g.: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C9H16N3O13P3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 467.1569 Monoisotopic: 466.989597149 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | RGWHQCVHVJXOKC-SHYZEUOFSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C9H16N3O13P3/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(23-8)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,13H,3-4H2,(H,18,19)(H,20,21)(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 2056-98-6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | ({[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | dCTP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: | Cytidine triphosphate + 2 Flavodoxin reduced + 2 Hydrogen ion > dCTP +2 flavodoxin semi oxidized + Water Adenosine triphosphate + dCDP <> ADP + dCTP dCTP + Water > dCMP + Hydrogen ion + Pyrophosphate dCTP + Hydrogen ion + Water > Deoxyuridine triphosphate + Ammonium dCTP + DNA <> Pyrophosphate + DNA dCTP + Thioredoxin disulfide + Water <> Cytidine triphosphate + Thioredoxin dCTP + Water <> Deoxyuridine triphosphate + Ammonia dCTP + Uridine <> dCDP + Uridine 5'-monophosphate dCTP + Cytidine <> dCDP + Cytidine monophosphate dCDP + Adenosine triphosphate > dCTP + ADP Water + dCTP > Ammonia + Deoxyuridine triphosphate Cytidine triphosphate + Water + dCTP <> Cytidine monophosphate + Pyrophosphate + dCMP dCDP + Adenosine triphosphate > Adenosine diphosphate + dCTP + ADP Cytidine triphosphate + a reduced flavodoxin > Water + an oxidized flavodoxin + dCTP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: | Hinz M; Gottschling D; Eritja R; Seliger H Synthesis and properties of 2'-deoxycytidine triphosphate carrying c-myc tag sequence. Nucleosides, nucleotides & nucleic acids (2000), 19(10-12), 1543-52. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in nucleic acid binding
- Specific function:
- In addition to polymerase activity, this DNA polymerase exhibits 3' to 5' and 5' to 3' exonuclease activity. It is able to utilize nicked circular duplex DNA as a template and can unwind the parental DNA strand from its template
- Gene Name:
- polA
- Uniprot ID:
- P00582
- Molecular weight:
- 103117
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in DNA binding
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. The epsilon subunit contain the editing function and is a proofreading 3'-5' exonuclease
- Gene Name:
- dnaQ
- Uniprot ID:
- P03007
- Molecular weight:
- 27099
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in nucleotide binding
- Specific function:
- The gamma chain seems to interact with the delta subunit to transfer the beta subunit on the DNA
- Gene Name:
- dnaX
- Uniprot ID:
- P06710
- Molecular weight:
- 71137
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- 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 DNA binding
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The beta chain is required for initiation of replication once it is clamped onto DNA, it slides freely (bidirectional and ATP- independent) along duplex DNA
- Gene Name:
- dnaN
- Uniprot ID:
- P0A988
- Molecular weight:
- 40586
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(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 DNA binding
- Specific function:
- The exact function of the theta subunit is unknown
- Gene Name:
- holE
- Uniprot ID:
- P0ABS8
- Molecular weight:
- 8846
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- 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 3'-5' exonuclease activity
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The alpha chain is the DNA polymerase
- Gene Name:
- dnaE
- Uniprot ID:
- P10443
- Molecular weight:
- 129903
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- 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 DNA binding
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The delta subunit seems to interact with the gamma subunit to transfer the beta subunit on the DNA
- Gene Name:
- holA
- Uniprot ID:
- P28630
- Molecular weight:
- 38703
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in DNA binding
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity
- Gene Name:
- holB
- Uniprot ID:
- P28631
- Molecular weight:
- 36936
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- General function:
- Involved in DNA-directed DNA polymerase activity
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity. The exact function of the psi subunit is unknown
- Gene Name:
- holD
- Uniprot ID:
- P28632
- Molecular weight:
- 15174
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- 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 DNA binding
- Specific function:
- DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity
- Gene Name:
- holC
- Uniprot ID:
- P28905
- Molecular weight:
- 16633
Reactions
Deoxynucleoside triphosphate + DNA(n) = diphosphate + DNA(n+1). |
- 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 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 hydrolase activity
- Specific function:
- Specific for pyrimidine substrates. Acts on 5-methyl- dCTP, CTP and dCTP in decreasing order
- Gene Name:
- nudG
- Uniprot ID:
- P77788
- Molecular weight:
- 15046
Reactions
CTP + H(2)O = CMP + diphosphate. |
- 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. |