3'-deoxyadenosine 5'-triphosphate profile

3'-deoxyadenosine 5'-triphosphate (3'-dATP) is a synthetic analog of adenosine triphosphate (ATP) in which the 3'-hydroxyl group of the ribose moiety is replaced with a hydrogen atom. This modification prevents the formation of a phosphodiester bond at the 3'-position, making 3'-dATP a chain terminator in DNA synthesis. It is commonly used in DNA sequencing, PCR, and other molecular biology techniques to determine the sequence of DNA. 3'-dATP is also used as a substrate for some DNA polymerases, such as terminal deoxynucleotidyl transferase (TdT), which can add 3'-dATP to the 3'-end of DNA strands. The use of 3'-dATP in these applications is based on its ability to be incorporated into DNA by DNA polymerases but not to be extended by the same enzymes. 3'-dATP is typically synthesized via chemical methods involving the phosphorylation of 3'-deoxyadenosine, a nucleoside analog that is obtained by chemical modification of adenosine. 3'-dATP has also been shown to have antiviral activity against certain viruses, such as HIV and herpes simplex virus. This activity is likely due to its ability to inhibit viral DNA replication.'

ID Source	ID
PubMed CID	65562
CHEMBL ID	480329
CHEBI ID	52316
SCHEMBL ID	250251
MeSH ID	M0058276

Synonym
3AT ,
3'-deoxyadenosine-5'-triphosphate
{[(2s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) dihydrogen phosphate
[[(2s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
3'datp
1XFV ,
DB01860
cordycepin triphosphate
73-04-1
CHEBI:52316 ,
cotp
3'-deoxyadenosine 5'-triphosphate
3'-deoxyadenosine 5'-(tetrahydrogen triphosphate)
[[(2s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
3'-datp
CHEMBL480329
bdbm86487
atp,3'-deoxy
59p84zu54h ,
adenosine 5'-(tetrahydrogen triphosphate), 3'-deoxy-
unii-59p84zu54h
71997-32-5
SCHEMBL250251
adenosine, 3'-deoxy-, 5'-triphosphate
adenosine, 3'-deoxy-, 5'-(tetrahydrogen triphosphate)
cordycepin 5'-triphosphate
3'-deoxy-atp
3'-deoxyadenosine triphosphate
3'-deoxyribofuranosyladenine 5'-triphosphate
cordycepin, triphosphate
cordycepin triphosphate [mi]
cordycepin 5-triphosphate sodium salt
((2s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
3-deoxyadenosine 5-triphosphate sodium salt
DTXSID501014467

Role	Description
antimetabolite	A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
antifungal agent	An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antineoplastic agent	A substance that inhibits or prevents the proliferation of neoplasms.
antiviral agent	A substance that destroys or inhibits replication of viruses.
[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]

Class	Description
purine ribonucleoside 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]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
RNA-directed RNA polymerase		IC50 (µMol)	8.8000	0.0190	2.5279	8.8000	AID340760
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, Calmodulin-sensitive adenylate cyclase	Bacillus anthracis	Kd	130.0000	130.0000	130.0000	130.0000	AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1811	Experimentally measured binding affinity data derived from PDB	2005	The EMBO journal, Mar-09, Volume: 24, Issue:5	Calcium-independent calmodulin binding and two-metal-ion catalytic mechanism of anthrax edema factor.
AID977611	Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB	2005	The EMBO journal, Mar-09, Volume: 24, Issue:5	Calcium-independent calmodulin binding and two-metal-ion catalytic mechanism of anthrax edema factor.
AID1537215	Inhibition of ZIKV N-terminal His6-tagged NS5 protein expressed in Escherichia coli using (Poly U) RNA template after 20 mins in presence of ATP by picogreen dye based assay	2019	Journal of natural products, 02-22, Volume: 82, Issue:2	Antiviral Compounds from Codiaeum peltatum Targeted by a Multi-informative Molecular Networks Approach.
AID340758	Inhibition of HCV NS5B polymerase assessed as chain termination of RNA synthesis	2007	Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8	Pyrophosphorolytic excision of nonobligate chain terminators by hepatitis C virus NS5B polymerase.
AID340761	Ratio of IC50 for HCV NS5B polymerase S282T mutant to IC50 for HCV NS5B polymerase by single-nucleotide incorporation assay	2007	Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8	Pyrophosphorolytic excision of nonobligate chain terminators by hepatitis C virus NS5B polymerase.
AID1674507	Inhibition of DENV RNA-dependent RNA polymerase at 10 uM	2020	Journal of natural products, 08-28, Volume: 83, Issue:8	Carneic Acids from an Endophytic
AID1537216	Inhibition of DENV2 N-terminal His6-tagged NS5 protein expressed in Escherichia coli using (Poly U) RNA template after 20 mins in presence of ATP by picogreen dye based assay	2019	Journal of natural products, 02-22, Volume: 82, Issue:2	Antiviral Compounds from Codiaeum peltatum Targeted by a Multi-informative Molecular Networks Approach.
AID340760	Inhibition of HCV NS5B polymerase S282T mutant assessed as blocking of full length RNA product formation by single-nucleotide incorporation assay	2007	Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8	Pyrophosphorolytic excision of nonobligate chain terminators by hepatitis C virus NS5B polymerase.
AID340759	Inhibition of HCV NS5B polymerase assessed as blocking of full length RNA product formation by single-nucleotide incorporation assay	2007	Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8	Pyrophosphorolytic excision of nonobligate chain terminators by hepatitis C virus NS5B polymerase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	14 (41.18)	18.7374
1990's	3 (8.82)	18.2507
2000's	10 (29.41)	29.6817
2010's	5 (14.71)	24.3611
2020's	2 (5.88)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	1 (2.94%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	33 (97.06%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
adenine [no description available]	2.87	4	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
phycoerythrin ara-ATP: structure	1.98	1	0
diphosphoric acid diphosphoric acid : An acyclic phosphorus acid anhydride obtained by condensation of two molecules of phosphoric acid.	1.94	1	0	acyclic phosphorus acid anhydride; phosphorus oxoacid	Escherichia coli metabolite
chloroquine Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.	2.21	1	0	aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound	anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug
9-(2-hydroxy-3-nonyl)adenine 9-(2-hydroxy-3-nonyl)adenine: specific inhibitor of adenosine deaminase	2.37	2	0
hydroxyurea [no description available]	3.42	1	1	one-carbon compound; ureas	antimetabolite; antimitotic; antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; genotoxin; immunomodulator; radical scavenger; teratogenic agent
potassium chloride Potassium Chloride: A white crystal or crystalline powder used in BUFFERS; FERTILIZERS; and EXPLOSIVES. It can be used to replenish ELECTROLYTES and restore WATER-ELECTROLYTE BALANCE in treating HYPOKALEMIA.. potassium chloride : A metal chloride salt with a K(+) counterion.	1.97	1	0	inorganic chloride; inorganic potassium salt; potassium salt	fertilizer
ficusin Ficusin: A naturally occurring furocoumarin, found in PSORALEA. After photoactivation with UV radiation, it binds DNA via single and double-stranded cross-linking.. psoralen : The simplest member of the class of psoralens that is 7H-furo[3,2-g]chromene having a keto group at position 7. It has been found in plants like Psoralea corylifolia and Ficus salicifolia.	2.08	1	0	psoralens	plant metabolite
cordycepin [no description available]	2.75	3	0	3'-deoxyribonucleoside; adenosines	antimetabolite; nucleoside antibiotic
trichloroacetic acid Trichloroacetic Acid: A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts.. trichloroacetic acid : A monocarboxylic acid that is acetic acid in which all three methyl hydrogens are substituted by chlorine.	2	1	0	monocarboxylic acid; organochlorine compound	carcinogenic agent; metabolite; mouse metabolite
dimethyl sulfate dimethyl sulfate: RN given refers to unlabeled cpd; structure. dimethyl sulfate : The dimethyl ester of sulfuric acid.	2	1	0	alkyl sulfate	alkylating agent; immunosuppressive agent
phosphoribosyl pyrophosphate Phosphoribosyl Pyrophosphate: The key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides.. 5-phosphoribosyl diphosphate : A ribose diphosphate carrying an additional phosphate group at position 5.. 5-O-phosphono-alpha-D-ribofuranosyl diphosphate : A derivative of alpha-D-ribose having a phosphate group at the 5-position and a diphosphate at the 1-position.	1.94	1	0	5-O-phosphono-D-ribofuranosyl diphosphate	Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite
deoxycytidine monophosphate Deoxycytidine Monophosphate: Deoxycytidine (dihydrogen phosphate). A deoxycytosine nucleotide containing one phosphate group esterified to the deoxyribose moiety in the 2'-,3'- or 5- positions.. 2'-deoxycytosine 5'-monophosphate : A pyrimidine 2'-deoxyribonucleoside 5'-monophosphate having cytosine as the nucleobase.	2.05	1	0	2'-deoxycytidine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-monophosphate	Escherichia coli metabolite; mouse metabolite
2'-deoxyadenosine triphosphate 2'-deoxyadenosine triphosphate: RN given refers to unlabeled parent cpd	2.36	2	0	2'-deoxyadenosine 5'-phosphate; purine 2'-deoxyribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	3.07	5	0	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
coformycin [no description available]	1.97	1	0	coformycins	EC 3.5.4.4 (adenosine deaminase) inhibitor
adenylyl imidodiphosphate Adenylyl Imidodiphosphate: 5'-Adenylic acid, monoanhydride with imidodiphosphoric acid. An analog of ATP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It is a potent competitive inhibitor of soluble and membrane-bound mitochondrial ATPase and also inhibits ATP-dependent reactions of oxidative phosphorylation.	1.97	1	0	adenosine 5'-phosphate
vidarabine phosphate Vidarabine Phosphate: An adenosine monophosphate analog in which ribose is replaced by an arabinose moiety. It is the monophosphate ester of VIDARABINE with antiviral and possibly antineoplastic properties.	1.98	1	0
vanadates Vanadates: Oxyvanadium ions in various states of oxidation. They act primarily as ion transport inhibitors due to their inhibition of Na(+)-, K(+)-, and Ca(+)-ATPase transport systems. They also have insulin-like action, positive inotropic action on cardiac ventricular muscle, and other metabolic effects.. vanadate(3-) : A vanadium oxoanion that is a trianion with formula VO4 in which the vanadium is in the +5 oxidation state and is attached to four oxygen atoms.	1.97	1	0	trivalent inorganic anion; vanadium oxoanion	EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; EC 3.1.3.41 (4-nitrophenylphosphatase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
deoxyuridine triphosphate [no description available]	2	1	0	deoxyuridine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-triphosphate	Arabidopsis thaliana metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite
2',3'-dideoxyadenosine triphosphate [no description available]	1.96	1	0	purine deoxyribonucleoside triphosphate
2'-5'-oligoadenylate trimer 2',5'-oligoadenylate: inhibits protein synthesis in cell-free systems	1.96	1	0
3'-deoxycytidine 5'-triphosphate [no description available]	2.71	3	0
pentostatin Pentostatin: A potent inhibitor of ADENOSINE DEAMINASE. The drug induces APOPTOSIS of LYMPHOCYTES, and is used in the treatment of many lymphoproliferative malignancies, particularly HAIRY CELL LEUKEMIA. It is also synergistic with some other antineoplastic agents and has immunosuppressive activity.. pentostatin : A member of the class of coformycins that is coformycin in which the hydroxy group at position 2' is replaced with a hydrogen. It is a drug used for the treatment of hairy cell leukaemia.	1.97	1	0	coformycins	antimetabolite; antineoplastic agent; Aspergillus metabolite; bacterial metabolite; EC 3.5.4.4 (adenosine deaminase) inhibitor
potassium permanganate Potassium Permanganate: Permanganic acid (HMnO4), potassium salt. A highly oxidative, water-soluble compound with purple crystals, and a sweet taste. (From McGraw-Hill Dictionary of Scientific and Technical Information, 4th ed)	2	1	0
bromochloroacetic acid Keratins: A class of fibrous proteins or scleroproteins that represents the principal constituent of EPIDERMIS; HAIR; NAILS; horny tissues, and the organic matrix of tooth ENAMEL. Two major conformational groups have been characterized, alpha-keratin, whose peptide backbone forms a coiled-coil alpha helical structure consisting of TYPE I KERATIN and a TYPE II KERATIN, and beta-keratin, whose backbone forms a zigzag or pleated sheet structure. alpha-Keratins have been classified into at least 20 subtypes. In addition multiple isoforms of subtypes have been found which may be due to GENE DUPLICATION.. bromochloroacetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by bromine while a second is replaced by chlorine. A low-melting (27.5-31.5degreeC), hygroscopic crystalline solid, it can be formed during the disinfection (by chlorination) of water that contains bromide ions and organic matter, so can occur in drinking water as a byproduct of the disinfection process.	1.97	1	0	2-bromocarboxylic acid; monocarboxylic acid; organochlorine compound
pyrophosphate Diphosphates: Inorganic salts of phosphoric acid that contain two phosphate groups.	1.94	1	0	diphosphate ion
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	1.95	1	0	ammonium salt; inorganic sulfate salt	fertilizer
oligonucleotides [no description available]	1.96	1	0
alpha-amanitin Alpha-Amanitin: A cyclic octapeptide with a thioether bridge between the cystine and tryptophan. It inhibits RNA POLYMERASE II. Poisoning may require LIVER TRANSPLANTATION.. alpha-amanitin : A heterodetic cyclic peptide consisting of eight amino acid residues and containing a thioether bridge between a cysteine and a tryptophan residue. It is found in a number of poisonous mushrooms, including Amanita phalloides (the death cap), Galerina marginata, and and Conocybe filaris.	2.05	1	0
piperidines Piperidines: A family of hexahydropyridines.	2	1	0
formycin triphosphate formycin triphosphate: formycin ATP analog	2.37	2	0
deoxyguanosine triphosphate [no description available]	2	1	0	deoxyguanosine phosphate; guanyl deoxyribonucleotide; purine 2'-deoxyribonucleoside 5'-triphosphate	Arabidopsis thaliana metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
didanosine Didanosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.. didanosine : A purine 2',3'-dideoxyribonucleoside that is inosine in which the hydroxy groups at both the 2' and the 3' positions on the sugar moiety have been replaced by hydrogen. An antiviral drug, it is used as a medication to treat HIV/AIDS.	3.42	1	1	purine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor; geroprotector; HIV-1 reverse transcriptase inhibitor
formycins Formycins: Pyrazolopyrimidine ribonucleosides isolated from Nocardia interforma. They are antineoplastic antibiotics with cytostatic properties.	2.37	2	0
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	2.4	2	0

Condition	Relationship Strength	Studies	Trials
Carcinoma, Anaplastic [description not available]	2.63	3	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.86	4	0
Experimental Neoplasms [description not available]	2.63	3	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.63	3	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	1.94	1	0
HIV Coinfection [description not available]	3.42	1	1
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	3.42	1	1
Kahler Disease [description not available]	2.04	1	0
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	2.04	1	0
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	1.96	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	1.96	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2	1	0
Hepatocellular Carcinoma [description not available]	1.95	1	0
Cancer of Liver [description not available]	1.95	1	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	1.95	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	1.95	1	0

3'-deoxyadenosine 5'-triphosphate

Cross-References

Synonyms (35)

Roles (4)

Drug Classes (1)

Protein Targets (2)

Inhibition Measurements

Activation Measurements

Ceullar Components (1)

Bioassays (9)

Research

Studies (34)

Market Indicators

Research Demand Index: 24.84

Study Types