Page last updated: 2024-11-06

2',3'-dideoxyadenosine triphosphate

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

2',3'-dideoxyadenosine triphosphate (ddATP) is a nucleoside analog that has been studied extensively for its antiviral and anticancer properties. It is a modified form of adenosine triphosphate (ATP), where the 2' and 3' hydroxyl groups on the ribose sugar have been removed. ddATP is a chain terminator, meaning it prevents the elongation of DNA by DNA polymerases. This is because its structure lacks the 3'-hydroxyl group needed for the formation of a phosphodiester bond between nucleotides during DNA replication. The synthesis of ddATP typically involves the chemical modification of adenosine triphosphate. ddATP's ability to terminate DNA replication makes it a valuable tool for studying the mechanisms of DNA replication, DNA repair, and viral replication. It is also used in the synthesis of DNA probes for gene detection and in the development of antiviral and anticancer therapies.'

Cross-References

ID SourceID
PubMed CID65304
CHEMBL ID1383
CHEBI ID172701
SCHEMBL ID79815
MeSH IDM0114061

Synonyms (35)

Synonym
CHEBI:172701
2',3'-dideoxyadenosine-5-triphosphate
[[(2s,5r)-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
[(2s,5r)-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl (hydroxy-phosphonooxyphosphoryl) hydrogen phosphate
gtpl1709
[[(2s,5r)-5-(6-aminopurin-9-yl)tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
adenosine 5'-(tetrahydrogen triphosphate), 2',3'-dideoxy-
ddatp
24027-80-3
2',3'-dideoxy-atp
dideoxyadenosine 5'-triphosphate
2',3'-dideoxyadenosine 5'-triphosphate
2',3'-ddatp
2',3'-dideoxyadenosine triphosphate
DB02189
bdbm50164644
dda-tp
[[[5-(6-amino-9h-purin-9-yl)tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxyphosphonic acid
atp,2',3'-dideoxy
2'',3''-dideoxyadenosine triphosphate
2'',3''-dideoxyadenosine triphosphate (ddatp)
dda-triphosphate
CHEMBL1383 ,
9mci2h1ej6 ,
unii-9mci2h1ej6
dideoxyadenosine 5'-triphosphate [mi]
SCHEMBL79815
dideoxyadenosine triphosphate
DTXSID90178767
AKOS030589611
((2s,5r)-5-(6-amino-9h-purin-9-yl)tetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
HY-128036
Q27071868
CS-0095043
(((2s,5r)-5-(6-amino-9h-purin-9-yl)tetrahydrofuran-2-yl)methyl)triphosphoric acid

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
"Didanosine (ddI) is used in the treatment of HIV-1 infection alone and in combination with azidothymidine (AZT)."( Pharmacodynamic studies (PD) of didanosine (ddI) alone and in combination with azidothymidine (AZT) in human T-cells; a stochastic biochemical approach to antiretroviral nucleoside drug combination in inhibiting HIV-reverse transcriptase (RT).
Avramis, VI; Nandy, P; Periclou, AP,
)
0.13

Dosage Studied

ExcerptRelevanceReference
"Measurement of intracellular drug levels in cell culture systems can be of predictive value in establishing rational clinical dosage schedules."( Decay rates of anti-HIV dideoxynucleotides in tissue culture systems: a simple correction for the effect of cell replication.
Ahluwalia, GS; Dedrick, RL; Driscoll, JS; Gao, WY; Johns, DG; Morrison, PF, 1997
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
purine deoxyribonucleoside 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 (1)

PathwayProteinsCompounds
Didanosine Action Pathway05

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA polymerase betaHomo sapiens (human)IC50 (µMol)8.40001.40006.56679.0000AID1614343
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Ki0.39500.00031.552310.0000AID167232; AID167234; AID198918; AID238445; AID341970; AID341972
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Kd5.30000.00062.40599.8000AID572771
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
nucleotide-excision repair, DNA gap fillingDNA polymerase betaHomo sapiens (human)
in utero embryonic developmentDNA polymerase betaHomo sapiens (human)
DNA-templated DNA replicationDNA polymerase betaHomo sapiens (human)
DNA repairDNA polymerase betaHomo sapiens (human)
base-excision repairDNA polymerase betaHomo sapiens (human)
base-excision repair, gap-fillingDNA polymerase betaHomo sapiens (human)
pyrimidine dimer repairDNA polymerase betaHomo sapiens (human)
inflammatory responseDNA polymerase betaHomo sapiens (human)
DNA damage responseDNA polymerase betaHomo sapiens (human)
salivary gland morphogenesisDNA polymerase betaHomo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damageDNA polymerase betaHomo sapiens (human)
response to gamma radiationDNA polymerase betaHomo sapiens (human)
somatic hypermutation of immunoglobulin genesDNA polymerase betaHomo sapiens (human)
response to ethanolDNA polymerase betaHomo sapiens (human)
lymph node developmentDNA polymerase betaHomo sapiens (human)
spleen developmentDNA polymerase betaHomo sapiens (human)
homeostasis of number of cellsDNA polymerase betaHomo sapiens (human)
neuron apoptotic processDNA polymerase betaHomo sapiens (human)
response to hyperoxiaDNA polymerase betaHomo sapiens (human)
immunoglobulin heavy chain V-D-J recombinationDNA polymerase betaHomo sapiens (human)
DNA biosynthetic processDNA polymerase betaHomo sapiens (human)
double-strand break repair via nonhomologous end joiningDNA polymerase betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
damaged DNA bindingDNA polymerase betaHomo sapiens (human)
DNA-directed DNA polymerase activityDNA polymerase betaHomo sapiens (human)
DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
protein bindingDNA polymerase betaHomo sapiens (human)
microtubule bindingDNA polymerase betaHomo sapiens (human)
lyase activityDNA polymerase betaHomo sapiens (human)
enzyme bindingDNA polymerase betaHomo sapiens (human)
metal ion bindingDNA polymerase betaHomo sapiens (human)
5'-deoxyribose-5-phosphate lyase activityDNA polymerase betaHomo sapiens (human)
class I DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
nucleusDNA polymerase betaHomo sapiens (human)
nucleoplasmDNA polymerase betaHomo sapiens (human)
cytoplasmDNA polymerase betaHomo sapiens (human)
microtubuleDNA polymerase betaHomo sapiens (human)
spindle microtubuleDNA polymerase betaHomo sapiens (human)
protein-containing complexDNA polymerase betaHomo sapiens (human)
nucleusDNA polymerase betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID1632252Inhibition of Escherichia coli DNA polymerase 1 Klenow fragment preincubated for 15 mins followed by addition of DNA substrate for 60 mins in presence of dNTPS/TAMRA tracer by fluorescence polarization assay2016Bioorganic & medicinal chemistry letters, 09-15, Volume: 26, Issue:18
A fluorescence polarization based assay for the identification and characterization of polymerase inhibitors.
AID341364Inhibition of human DNA polymerase gamma using calf thymus DNA as a template2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Activity against human immunodeficiency virus type 1, intracellular metabolism, and effects on human DNA polymerases of 4'-ethynyl-2-fluoro-2'-deoxyadenosine.
AID228136Ratio of inhibitory activity of compound to that of substrate activity of dATP against RT M184I enzyme was determined2003Journal of medicinal chemistry, Oct-23, Volume: 46, Issue:22
Inhibition of human immunodeficiency virus reverse transcriptase by synadenol triphosphate and its E-isomer.
AID341972Inhibition of HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant by steady state nucleotide incorporation assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID167234Inhibitory activity against HIV-1 reverse transcriptase (RT M184V)2003Journal of medicinal chemistry, Oct-23, Volume: 46, Issue:22
Inhibition of human immunodeficiency virus reverse transcriptase by synadenol triphosphate and its E-isomer.
AID341363Inhibition of human DNA polymerase gamma using D21/D36 DNA as a template2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Activity against human immunodeficiency virus type 1, intracellular metabolism, and effects on human DNA polymerases of 4'-ethynyl-2-fluoro-2'-deoxyadenosine.
AID198918Inhibitory activity against HIV-1 Reverse transcriptase wild-type (RT wt)2003Journal of medicinal chemistry, Oct-23, Volume: 46, Issue:22
Inhibition of human immunodeficiency virus reverse transcriptase by synadenol triphosphate and its E-isomer.
AID341178Inhibition of human DNA polymerase alpha using calf thymus DNA as a template2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Activity against human immunodeficiency virus type 1, intracellular metabolism, and effects on human DNA polymerases of 4'-ethynyl-2-fluoro-2'-deoxyadenosine.
AID228138Ratio of inhibitory activity of compound to that of substrate activity of dATP against RT wt enzyme was determined2003Journal of medicinal chemistry, Oct-23, Volume: 46, Issue:22
Inhibition of human immunodeficiency virus reverse transcriptase by synadenol triphosphate and its E-isomer.
AID1614344Inhibition of human DNA polymerase gamma using 5-end radiolabeled 24nt to 48nt DNA as primer template after 120 mins in presence of dCTP/dGTP/dTTP/dATP by PAGE analysis2019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
Discovery of a Series of 2'-α-Fluoro,2'-β-bromo-ribonucleosides and Their Phosphoramidate Prodrugs as Potent Pan-Genotypic Inhibitors of Hepatitis C Virus.
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.
AID572773Selectivity, ratio of Kpol to Kd for dATP to Kpol to Kd for compound at 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.
AID1614343Inhibition of human DNA polymerase beta using 5-end radiolabeled 24nt to 48nt DNA as primer template after 5 mins in presence of dCTP/dGTP/dTTP/dATP by PAGE analysis2019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
Discovery of a Series of 2'-α-Fluoro,2'-β-bromo-ribonucleosides and Their Phosphoramidate Prodrugs as Potent Pan-Genotypic Inhibitors of Hepatitis C Virus.
AID341975Ratio of Ki/Km for HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant to Ki/Km for wild-type reverse transcriptase2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID1632253Inhibition of Escherichia coli DNA polymerase 1 Klenow fragment preincubated for 15 mins followed by addition of DNA substrate for 60 mins in presence of dNTPS by picoGreen reagent based assay2016Bioorganic & medicinal chemistry letters, 09-15, Volume: 26, Issue:18
A fluorescence polarization based assay for the identification and characterization of polymerase inhibitors.
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.
AID167232Inhibitory activity against HIV-1 reverse transcriptase (RT M184I)2003Journal of medicinal chemistry, Oct-23, Volume: 46, Issue:22
Inhibition of human immunodeficiency virus reverse transcriptase by synadenol triphosphate and its E-isomer.
AID341361Inhibition of human DNA polymerase beta using D21/D36 DNA as a template2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Activity against human immunodeficiency virus type 1, intracellular metabolism, and effects on human DNA polymerases of 4'-ethynyl-2-fluoro-2'-deoxyadenosine.
AID228137Ratio of inhibitory activity of compound to that of substrate activity of dATP against RT M184V enzyme was determined2003Journal of medicinal chemistry, Oct-23, Volume: 46, Issue:22
Inhibition of human immunodeficiency virus reverse transcriptase by synadenol triphosphate and its E-isomer.
AID341971Ratio of Ki to Km for HIV1 reverse transcriptase by steady state nucleotide incorporation assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
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.
AID341970Inhibition of HIV1 reverse transcriptase by steady state nucleotide incorporation assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID341974Ratio of Ki to Km for HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant by steady state nucleotide incorporation assay2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID238445Inhibitory constant against HIV-1 reverse transcriptase2005Journal of medicinal chemistry, Apr-07, Volume: 48, Issue:7
Synthesis of 2',3'-dideoxynucleoside 5'-alpha-P-borano-beta,gamma-(difluoromethylene)triphosphates and their inhibition of HIV-1 reverse transcriptase.
AID341973Ratio of Ki for HIV1 reverse transcriptase M41L/D67N/L210W/T215Y mutant to Ki for wild-type reverse transcriptase2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Effects of the translocation status of human immunodeficiency virus type 1 reverse transcriptase on the efficiency of excision of tenofovir.
AID197929Concentration required to inhibit the HIV-1 recombinant Reverse Transcriptase (rRT) activity by 50%. Activated calf thymus DNA was used as template primer1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
Synthesis and evaluation of the anti-HIV activity of aza and deaza analogues of isoddA and their phosphates as prodrugs.
AID341362Inhibition of human DNA polymerase beta using calf thymus DNA as a template2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Activity against human immunodeficiency virus type 1, intracellular metabolism, and effects on human DNA polymerases of 4'-ethynyl-2-fluoro-2'-deoxyadenosine.
AID1346309Human P2Y1 receptor (P2Y receptors)1997British journal of pharmacology, May, Volume: 121, Issue:2
An examination of deoxyadenosine 5'(alpha-thio)triphosphate as a ligand to define P2Y receptors and its selectivity as a low potency partial agonist of the P2Y1 receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (65)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (7.69)18.7374
1990's31 (47.69)18.2507
2000's21 (32.31)29.6817
2010's6 (9.23)24.3611
2020's2 (3.08)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.85

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.85 (24.57)
Research Supply Index4.25 (2.92)
Research Growth Index5.16 (4.65)
Search Engine Demand Index13.88 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.85)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (2.99%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other65 (97.01%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]