Page last updated: 2024-12-06

2'-deoxycytidine 5'-triphosphate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2'-deoxycytidine 5'-triphosphate, commonly abbreviated as dCTP, is a nucleoside triphosphate that plays a crucial role in DNA replication and repair. It is a precursor for the synthesis of DNA, providing the cytosine base for the growing DNA chain. dCTP is incorporated into DNA by DNA polymerase enzymes during the replication process, where it pairs with guanine. Its synthesis involves a complex pathway that begins with the reduction of cytidine 5'-triphosphate (CTP) to deoxycytidine 5'-triphosphate (dCTP) by the enzyme ribonucleotide reductase. dCTP is also involved in other cellular processes, such as DNA repair and signal transduction. Studies on dCTP focus on understanding its role in DNA synthesis, its potential as a therapeutic target for cancer treatment, and its contribution to various genetic disorders. Research into dCTP also investigates its interactions with DNA polymerase and other enzymes involved in DNA metabolism. The compound is also studied in the context of antiviral therapies, as it can be utilized to inhibit the replication of certain viruses. '

2'-deoxycytidine 5'-triphosphate: RN given refers to unlabeled parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65091
CHEMBL ID560403
CHEBI ID16311
SCHEMBL ID42135
MeSH IDM0082046

Synonyms (38)

Synonym
CHEBI:16311 ,
2'-deoxycytidine 5'-(tetrahydrogen triphosphate)
[[[(2r,3s,5r)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3-hydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxyphosphonic acid
cytidine, 2'-deoxy-, triphosphate
5'-dctp
deoxy-5'-ctp
4-amino-1-[2-deoxy-5-o-(hydroxy{[hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl)-beta-d-erythro-pentofuranosyl]pyrimidin-2(1h)-one
cytidine 5'-(tetrahydrogen triphosphate), 2'-deoxy-
2(1h)-pyrimidinone, 4-amino-1-[2-deoxy-5-o-[hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]-beta-d-erythro-pentofuranosyl]-
cytidine, 2'-deoxy-, 5'-(tetrahydrogen triphosphate)
2'-deoxycytidine 5'-triphosphate
DCTP ,
2056-98-6
deoxy-ctp
C00458
deoxycytidine-triphosphate
deoxycytidine 5'-triphosphate
deoxycytidine triphosphate
102783-51-7
[[(2r,3s,5r)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
2'-dctp
DB03258
[[(2r,3s,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
CHEMBL560403
einecs 218-153-9
EPITOPE ID:149168
SCHEMBL42135
((2r,3s,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
deoxycytidine-5'-triphosphate
RGWHQCVHVJXOKC-SHYZEUOFSA-N
AKOS024464457
2''''-deoxycytidine 5''''-triphosphate
bdbm50480766
HY-101400
CS-6402
Q424680
DTXSID60942755
((2r,3s,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)-3-hydroxytetrahydrofuran-2-yl)methyltetrahydrogentriphosphate

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Virtually non toxic concentrations of dThd potentiated the cytotoxicity of MNNG more than 10-fold but that of MMS was potentiated only about 2-fold showing that O-alkylation of DNA was associated not only with the facilitation of mutagenesis but also with the potentiation of cytotoxicity."( Deoxyribonucleoside-induced selective modulation of cytotoxicity and mutagenesis.
Danenberg, PV; Ibric, LL; Peterson, AR; Peterson, H, 1985
)
0.27
" In cell culture (-)3TC is less toxic than its d(+) isomer, (+)3TC, containing the natural nucleoside configuration, and both are considerably less toxic than ddC."( Insights into the molecular mechanism of mitochondrial toxicity by AIDS drugs.
Anderson, KS; Feng, JY; Johnson, AA; Johnson, KA, 2001
)
0.31

Pharmacokinetics

ExcerptReferenceRelevance
"To study the effect of mycophenolate mofetil therapy on the pharmacokinetic parameters of a number of antiretroviral drugs, on intracellular pools of deoxycytidine triphosphate (dCTP) and deoxyguanosine triphosphate (dGTP), and on intracellular concentrations of the triphosphate of lamivudine (3TCTP)."( Effect of mycophenolate mofetil on the pharmacokinetics of antiretroviral drugs and on intracellular nucleoside triphosphate pools.
Back, DJ; Beijnen, JH; Crommentuyn, KM; Hoggard, PG; Huitema, AD; Kewn, S; Lange, JM; Prins, JM; Sankatsing, SU; Sparidans, RW, 2004
)
0.32
"Randomised pharmacokinetic study."( Effect of mycophenolate mofetil on the pharmacokinetics of antiretroviral drugs and on intracellular nucleoside triphosphate pools.
Back, DJ; Beijnen, JH; Crommentuyn, KM; Hoggard, PG; Huitema, AD; Kewn, S; Lange, JM; Prins, JM; Sankatsing, SU; Sparidans, RW, 2004
)
0.32
" After 8 weeks of therapy, the plasma pharmacokinetic profiles of mycophenolic acid (the active metabolite of mycophenolate mofetil), abacavir, indinavir and nevirapine, and triphosphate concentrations (dCTP, dGTP and 3TCTP) in peripheral blood mononuclear cells, were determined."( Effect of mycophenolate mofetil on the pharmacokinetics of antiretroviral drugs and on intracellular nucleoside triphosphate pools.
Back, DJ; Beijnen, JH; Crommentuyn, KM; Hoggard, PG; Huitema, AD; Kewn, S; Lange, JM; Prins, JM; Sankatsing, SU; Sparidans, RW, 2004
)
0.32

Dosage Studied

ExcerptRelevanceReference
" These in vitro studies support our hypothesis that enhanced metabolism of ara-C in DS cells may be a contributing factor to the superior survival rate of DS children with AML and is possibly based on a gene dosage effect of genes localized to chromosome 21 including cystathionine-beta-synthase."( Enhanced metabolism of 1-beta-D-arabinofuranosylcytosine in Down syndrome cells: a contributing factor to the superior event free survival of Down syndrome children with acute myeloid leukemia.
Buck, SA; Gurney, JG; Matherly, LH; Ravindranath, Y; Stout, ML; Taub, JW, 1996
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
2'-deoxycytidine phosphate
pyrimidine 2'-deoxyribonucleoside 5'-triphosphate
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (10)

PathwayProteinsCompounds
Pyrimidine Metabolism2353
beta-Ureidopropionase Deficiency2353
UMP Synthase Deficiency (Orotic Aciduria)2353
Dihydropyrimidinase Deficiency2353
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)2353
Pyrimidine Deoxyribonucleosides Salvage815
Pyrimidine Nucleotides and Nucleosides metabolism ( Pyrimidine Nucleotides and Nucleosides metabolism )4549
ATP + dCDP = ADP + dCTP ( Pyrimidine Nucleotides and Nucleosides metabolism )74
Pyrimidine synthesis and deprivation pathway (COVID-19 Disease Maps)1329
Biochemical pathways: part I0466
Pyrimidine metabolism038

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Kd1.79000.00062.40599.8000AID432585; AID432586; AID432587; AID432588; AID572771
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Km3.74000.07001.91446.9000AID711539
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID432587Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID229453Efficiency expressed as ratio of Vmax to that of Km was determined2002Bioorganic & medicinal chemistry letters, Jan-07, Volume: 12, Issue:1
2-Amino-7-deazaadenine forms stable base pairs with cytosine and thymine.
AID432618Ratio of Kpol to Kd for HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V mutant2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID572771Binding affinity to HIV1 reverse transcriptase2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Anti-human immunodeficiency virus activity, cross-resistance, cytotoxicity, and intracellular pharmacology of the 3'-azido-2',3'-dideoxypurine nucleosides.
AID432589Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V/G333D mutant2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID1124519Inhibition of human mitochondrial thymidine kinase using [14C]thymidine after 10 mins by liquid scintillation spectrometer analysis relative to control in presence of Mg2+1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Design of species- or isozyme-specific enzyme inhibitors. 1. Effect of thymidine substituents on affinity for the thymidine site of hamster cytoplasmic thymidine kinase.
AID432619Ratio of Kpol to Kd for HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V/G333D mutant2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID572772Ratio of Kpol to Kd for HIV1 reverse transcriptase2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Anti-human immunodeficiency virus activity, cross-resistance, cytotoxicity, and intracellular pharmacology of the 3'-azido-2',3'-dideoxypurine nucleosides.
AID18096Kinetic parameter Km was determined2002Bioorganic & medicinal chemistry letters, Jan-07, Volume: 12, Issue:1
2-Amino-7-deazaadenine forms stable base pairs with cytosine and thymine.
AID711539Activity of HIV1 reverse transcriptase2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Synopsis of some recent tactical application of bioisosteres in drug design.
AID1124516Inhibition of thymidine kinase in BHK21 (C13) cells using [14C]thymidine after 10 mins by liquid scintillation spectrometer analysis relative to control in presence of Mg2+1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Design of species- or isozyme-specific enzyme inhibitors. 1. Effect of thymidine substituents on affinity for the thymidine site of hamster cytoplasmic thymidine kinase.
AID432586Binding affinity to HIV1 LAI reverse transcriptase M184V mutant2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432588Binding affinity to HIV1 LAI reverse transcriptase M41L/L210W/T215Y/M184V mutant2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432585Binding affinity to wild type HIV1 LAI reverse transcriptase2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID1124511Inhibition of human cytoplasmic thymidine kinase using [14C]thymidine after 10 mins by liquid scintillation spectrometer analysis relative to control in presence of Mg2+1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Design of species- or isozyme-specific enzyme inhibitors. 1. Effect of thymidine substituents on affinity for the thymidine site of hamster cytoplasmic thymidine kinase.
AID22610Kinetic parameter Vmax was determined2002Bioorganic & medicinal chemistry letters, Jan-07, Volume: 12, Issue:1
2-Amino-7-deazaadenine forms stable base pairs with cytosine and thymine.
AID572770Activity at HIV1 reverse transcriptase measured after 30 mins2009Antimicrobial agents and chemotherapy, Sep, Volume: 53, Issue:9
Anti-human immunodeficiency virus activity, cross-resistance, cytotoxicity, and intracellular pharmacology of the 3'-azido-2',3'-dideoxypurine nucleosides.
AID432615Ratio of Kpol to Kd for wild type HIV1 LAI reverse transcriptase2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432617Ratio of Kpol to Kd for HIV1 LAI reverse transcriptase M41L/L210W/T215Y mutant2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID432616Ratio of Kpol to Kd for HIV1 LAI reverse transcriptase M184V mutant2008Antimicrobial agents and chemotherapy, Jan, Volume: 52, Issue:1
Mechanisms by which the G333D mutation in human immunodeficiency virus type 1 Reverse transcriptase facilitates dual resistance to zidovudine and lamivudine.
AID711538Ratio of Vmax to Km for HIV1 reverse transcriptase2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Synopsis of some recent tactical application of bioisosteres in drug design.
AID711522Activity of HIV1 reverse transcriptase assessed per unit of protein2011Journal of medicinal chemistry, Apr-28, Volume: 54, Issue:8
Synopsis of some recent tactical application of bioisosteres in drug design.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (426)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990103 (24.18)18.7374
1990's126 (29.58)18.2507
2000's122 (28.64)29.6817
2010's71 (16.67)24.3611
2020's4 (0.94)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.54

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index13.54 (24.57)
Research Supply Index6.08 (2.92)
Research Growth Index4.44 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (13.54)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (0.69%)5.53%
Reviews7 (1.61%)6.00%
Case Studies2 (0.46%)4.05%
Observational0 (0.00%)0.25%
Other423 (97.24%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]