CHEBI:16311 - dCTP

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ChEBI Name dCTP
ChEBI ID CHEBI:16311
Definition A 2'-deoxycytidine phosphate having cytosine as the nucleobase.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:19243, CHEBI:41805, CHEBI:10494, CHEBI:14072
Supplier Information eMolecules:31267425, ZINC000008215945
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Deoxycytidine triphosphate (dCTP) is a nucleoside triphosphate that contains the pyrimidine base cytosine. The triphosphate group contains high-energy phosphoanhydride bonds, which liberate energy when hydrolized. DNA polymerase enzymes use this energy to incorporate deoxycytidine into a newly synthesized strand of DNA. A chemical equation can be written that represents the process: (DNA)n + dCTP ↔ (DNA)n-C + PPi That is, dCTP has the PPi (pyrophosphate) cleaved off and the dCMP is incorporated into the DNA strand at the 3' end. Subsequent hydrolysis of the PPi drives the equilibrium of the reaction toward the right side, i.e. incorporation of the nucleotide in the growing DNA chain. Like other nucleoside triphosphates, manufacturers recommend that dCTP be stored in aqueous solution at −20 °C.
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Formula C9H16N3O13P3
Net Charge 0
Average Mass 467.156
Monoisotopic Mass 466.98960
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
InChIKey RGWHQCVHVJXOKC-SHYZEUOFSA-N
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
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Escherichia coli (NCBI:txid562) Found in whole organism (UBERON:0000468). From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606) See: DOI
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via nucleoside 5'-triphoshate )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dCTP (CHEBI:16311) has role Escherichia coli metabolite (CHEBI:76971)
dCTP (CHEBI:16311) has role human metabolite (CHEBI:77746)
dCTP (CHEBI:16311) has role mouse metabolite (CHEBI:75771)
dCTP (CHEBI:16311) is a 2'-deoxycytidine phosphate (CHEBI:37092)
dCTP (CHEBI:16311) is a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate (CHEBI:37043)
dCTP (CHEBI:16311) is conjugate acid of dCTP(3−) (CHEBI:57724)
Incoming 5-iododeoxycytidine triphosphate (CHEBI:86351) has functional parent dCTP (CHEBI:16311)
dCTP(3−) (CHEBI:57724) is conjugate base of dCTP (CHEBI:16311)
IUPAC Name
2'-deoxycytidine 5'-(tetrahydrogen triphosphate)
Synonyms Sources
2'-deoxy-CTP ChEBI
2'-deoxycytidine 5'-triphosphate KEGG COMPOUND
2'-deoxycytidine triphosphate ChEBI
dCTP KEGG COMPOUND
deoxy-CTP HMDB
deoxycytidine 5'-triphosphate KEGG COMPOUND
deoxycytidine triphosphate KEGG COMPOUND
deoxycytidine-triphosphate HMDB
Manual Xrefs Databases
58601 ChemSpider
C00458 KEGG COMPOUND
DB03258 DrugBank
DCP PDBeChem
Deoxycytidine_triphosphate Wikipedia
FDB022359 FooDB
HMDB0000998 HMDB
View more database links
Registry Number Type Source
2056-98-6 CAS Registry Number ChemIDplus
Citations
Kapustina Ž, Jasponė A, Dubovskaja V, Mackevičius G, Lubys A (2021)
Enzymatic Synthesis of Chimeric DNA Oligonucleotides by in Vitro Transcription with dTTP, dCTP, dATP, and 2'-Fluoro Modified dGTP.
ACS synthetic biology 10, 1625-1632 [PubMed:34110794]
[show Abstract]
Li K, Luo Y, Huang K, Yang Z, Wan Y, Xu W (2020)
Single universal primer recombinase polymerase amplification-based lateral flow biosensor (SUP-RPA-LFB) for multiplex detection of genetically modified maize.
Analytica chimica acta 1127, 217-224 [PubMed:32800127]
[show Abstract]
Martínez-Arribas B, Requena CE, Pérez-Moreno G, Ruíz-Pérez LM, Vidal AE, González-Pacanowska D (2020)
DCTPP1 prevents a mutator phenotype through the modulation of dCTP, dTTP and dUTP pools.
Cellular and molecular life sciences : CMLS 77, 1645-1660 [PubMed:31377845]
[show Abstract]
Kandeel M, Al-Taher A (2020)
Metabolic drug targets of the cytosine metabolism pathways in the dromedary camel (Camelus dromedarius) and blood parasite Trypanosoma evansi.
Tropical animal health and production 52, 3337-3358 [PubMed:32926292]
[show Abstract]
Fesenko DO, Guseinov TO, Lapa SA, Kuznetsova VE, Shershov VE, Spitsyn MA, Nasedkina TV, Zasedatelev AS, Chudinov AV (2018)
[Substrate Properties of New Fluorescently Labeled Deoxycytidine Triphosphates in Enzymatic Synthesis of DNA with Polymerases of Families A and B].
Molekuliarnaia biologiia 52, 533-542 [PubMed:29989586]
[show Abstract]
Huang SW, Tzeng HF (2012)
Simultaneous determination of deoxycytidine diphosphate and deoxycytidine triphosphate by capillary electrophoresis with transient isotachophoretic stacking: a sensitive monitoring method for ribonucleotide reductase activity.
Electrophoresis 33, 536-542 [PubMed:22212996]
[show Abstract]
Crauste C, Lefebvre I, Hovaneissian M, Puy JY, Roy B, Peyrottes S, Cohen S, Guitton J, Dumontet C, Perigaud C (2009)
Development of a sensitive and selective LC/MS/MS method for the simultaneous determination of intracellular 1-beta-D-arabinofuranosylcytosine triphosphate (araCTP), cytidine triphosphate (CTP) and deoxycytidine triphosphate (dCTP) in a human follicular lymphoma cell line.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 877, 1417-1425 [PubMed:19328748]
[show Abstract]
Yamauchi T, Ueda T (2005)
A sensitive new method for clinically monitoring cytarabine concentrations at the DNA level in leukemic cells.
Biochemical pharmacology 69, 1795-1803 [PubMed:15935150]
[show Abstract]
Choi JY, Guengerich FP (2005)
Adduct size limits efficient and error-free bypass across bulky N2-guanine DNA lesions by human DNA polymerase eta.
Journal of molecular biology 352, 72-90 [PubMed:16061253]
[show Abstract]
van 't Wout AB (2005)
Gene expression profiling of HIV-1 infection using cDNA microarrays.
Methods in molecular biology (Clifton, N.J.) 304, 455-459 [PubMed:16061997]
[show Abstract]
Moriarty TJ, Marie-Egyptienne DT, Autexier C (2005)
Regulation of 5' template usage and incorporation of noncognate nucleotides by human telomerase.
RNA (New York, N.Y.) 11, 1448-1460 [PubMed:16120835]
[show Abstract]
Brzeziańska E, Zdzieszyńska M, Goś R, Lewiński A (2004)
[Genetic analysis of rhodopsin and peripherin genes in patients with autosomal dominant retinitis pigmentosa (adRP) in Polish families].
Klinika oczna 106, 743-748 [PubMed:15787173]
[show Abstract]
Hinz M, Gottschling D, Eritja R, Seliger H (2000)
Synthesis and properties of 2'-deoxycytidine triphosphate carrying c-myc tag sequence.
Nucleosides, nucleotides & nucleic acids 19, 1543-1552 [PubMed:11200258]
[show Abstract]
Traut TW (1994)
Physiological concentrations of purines and pyrimidines.
Molecular and cellular biochemistry 140, 1-22 [PubMed:7877593]
[show Abstract]
Flickinger RA, Richman R (1983)
Incorporation of deoxycytidine triphosphate and thymidine triphosphate into nuclear DNA in vitro during early and late S phase in frog embryos.
Cell differentiation 12, 233-237 [PubMed:6601514]
Harris AW, Reynolds EC, Finch LR (1979)
Effect of thymidine on the sensitivity of cultured mouse tumor cells to 1-beta-D-arabinofuranosylcytosine.
Cancer research 39, 538-541 [PubMed:761229]
[show Abstract]
Last Modified
27 July 2021