THYMIDINE TRIPHOSPHATE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H17N2O14P3
Molecular Weight	482.1683
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O

InChI

InChIKey=NHVNXKFIZYSCEB-XLPZGREQSA-N

InChI=1S/C10H17N2O14P3/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(24-8)4-23-28(19,20)26-29(21,22)25-27(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,21,22)(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C10H17N2O14P3
Molecular Weight	482.1683
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Gag-Pol polyprotein 6 Target ID: P04585 Gene ID: 155348.0 Gene Symbol: gag-pol Target Organism: Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)\|\|\|(HIV-1) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15801860	Interacts 323		0.061 µM [Ki]

PubMed

Title	Date	PubMed
Effects of substitutions at the 4' and 2 positions on the bioactivity of 4'-ethynyl-2-fluoro-2'-deoxyadenosine.	2013-12	24100493
Balancing antiviral potency and host toxicity: identifying a nucleotide inhibitor with an optimal kinetic phenotype for HIV-1 reverse transcriptase.	2012-07	22513406
Impact of novel human immunodeficiency virus type 1 reverse transcriptase mutations P119S and T165A on 4'-ethynylthymidine analog resistance profile.	2009-11	19704131
Theoretical basis for reducing time-lines to the determination of positive Mycobacterium tuberculosis cultures using thymidylate kinase (TMK) assays.	2009-03-18	19296833
Hepatitis C virus helicase/NTPase: an efficient expression system and new inhibitors.	2008-06	18620531
Structural studies of nucleoside analog and feedback inhibitor binding to Drosophila melanogaster multisubstrate deoxyribonucleoside kinase.	2008-05	18384378
Highly selective action of triphosphate metabolite of 4'-ethynyl D4T: a novel anti-HIV compound against HIV-1 RT.	2007-03	17109975
Synthesis of 2',3'-dideoxynucleoside 5'-alpha-P-borano-beta,gamma-(difluoromethylene)triphosphates and their inhibition of HIV-1 reverse transcriptase.	2005-04-07	15801860
Mechanistic insights into the suppression of drug resistance by human immunodeficiency virus type 1 reverse transcriptase using alpha-boranophosphate nucleoside analogs.	2005-02-04	15550379
Drug resistance mutations in the nucleotide binding pocket of human immunodeficiency virus type 1 reverse transcriptase differentially affect the phosphorolysis-dependent primer unblocking activity in the presence of stavudine and zidovudine and its inhibition by efavirenz.	2005-01	15616314
Borano-nucleotides: new analogues to circumvent HIV-1 RT-mediated nucleoside drug-resistance.	2005	16247962
Antibodies to guanosine triphosphate misidentified as anti-double-stranded DNA antibodies in a patient with antinuclear antibody-negative lupus, due to buckling of insolubilized assay DNA.	2004-05	15146423
Dioxolane guanosine 5'-triphosphate, an alternative substrate inhibitor of wild-type and mutant HIV-1 reverse transcriptase. Steady state and pre-steady state kinetic analyses.	2003-05-23	12651859
Nevirapine resistance mutation at codon 181 of the HIV-1 reverse transcriptase confers stavudine resistance by increasing nucleotide substrate discrimination and phosphorolytic activity.	2003-05-02	12601008
Introduction of the alpha-P-borano-group into deoxynucleoside triphosphates increases their selectivity to HIV-1 reverse transcriptase relative to DNA polymerases.	2003-03	12816386
Assessment of the effect of phosphorylated metabolites of anti-human immunodeficiency virus and anti-hepatitis B virus pyrimidine analogs on the behavior of human deoxycytidylate deaminase.	2003-01	12488542
The valine-to-threonine 75 substitution in human immunodeficiency virus type 1 reverse transcriptase and its relation with stavudine resistance.	2001-04-27	11134027
Inhibition of the initiation of HIV-1 reverse transcription by 3'-azido-3'-deoxythymidine. Comparison with elongation.	2000-09-01	10864929
Structural basis for activation of alpha-boranophosphate nucleotide analogues targeting drug-resistant reverse transcriptase.	2000-07-17	10899107
Mechanism of inhibition of the human immunodeficiency virus type 1 reverse transcriptase by d4TTP: an equivalent incorporation efficiency relative to the natural substrate dTTP.	2000-01	10602755
Structural determinants of HIV-1 reverse transcriptase stereoselectivity towards (beta)-L-deoxy- and dideoxy-pyrimidine nucleoside triphosphates: molecular basis for the combination of L-dideoxynucleoside analogs with non-nucleoside inhibitors in anti HIV chemotherapy.	1999-08-05	10432681
A mechanism of AZT resistance: an increase in nucleotide-dependent primer unblocking by mutant HIV-1 reverse transcriptase.	1999-07	10445025
Characterization and mutational analysis of the helicase and NTPase activities of hepatitis C virus full-length NS3 protein.	1999-03	10092010
Human immunodeficiency virus type 1 reverse transcriptase expressing the K70E mutation exhibits a decrease in specific activity and processivity.	1998-08	9687570
Comparative enzymatic study of HIV-1 reverse transcriptase resistant to 2',3'-dideoxynucleotide analogs using the single-nucleotide incorporation assay.	1997-02-04	9033399
Enzymatic characterization of human immunodeficiency virus type 1 reverse transcriptase resistant to multiple 2',3'-dideoxynucleoside 5'-triphosphates.	1995-10-06	7559526
Inhibition of human immunodeficiency virus type 1 reverse transcriptase by the 5'-triphosphate beta enantiomers of cytidine analogs.	1994-10	7530932
Inhibition of human immunodeficiency virus type 1 integrase by 3'-azido-3'-deoxythymidylate.	1994-06-21	8016063
Chiral discrimination of enantiomeric 2'-deoxythymidine 5'-triphosphate by HIV-1 reverse transcriptase and eukaryotic DNA polymerases.	1994-04-29	7513992
Lack of synergy in the inhibition of HIV-1 reverse transcriptase by combinations of the 5'-triphosphates of various anti-HIV nucleoside analogs.	1993-12	7506513
RNA-stimulated NTPase activity associated with yellow fever virus NS3 protein expressed in bacteria.	1993-02	8380474
Beta-L-thymidine 5'-triphosphate analogs as DNA polymerase substrates.	1992-12-15	1281153
Purification and characterization of two different thymidine-5'-triphosphosphate-hydrolysing enzymes in human serum.	1992-05	1320895
HIV-1 reverse transcriptase inhibition by a dipyridodiazepinone derivative: BI-RG-587.	1992-03-17	1373283
Human immunodeficiency virus reverse transcriptase. Substrate and inhibitor kinetics with thymidine 5'-triphosphate and 3'-azido-3'-deoxythymidine 5'-triphosphate.	1990-11-25	1700787
Reverse transcriptases from human immunodeficiency virus type 1 (HIV-1), HIV-2, and simian immunodeficiency virus (SIVMAC) are susceptible to inhibition by foscarnet and 3'-azido-3'-deoxythymidine triphosphate.	1988-11	2472774
Inhibition of HIV reverse transcriptase by 2',3'-dideoxynucleoside triphosphates.	1987-12-15	2446633
Separation of deoxythymidine-5'-triphosphatase from unspecific hydrolases. A recommended micromethod in the diagnostic evaluation of human carcinoma.	1984-07-01	6091528
Human serum thymidine triphosphate nucleotidohydrolase: purification and properties of a new enzyme.	1982-12-21	6297538

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:57:00 GMT 2025` Edited by `admin` on `Mon Mar 31 19:57:00 GMT 2025`
Record UNII	QOP4K539MU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2'-DEOXYTHYMIDINE TRIPHOSPHATE

Preferred Name

English

THYMIDINE TRIPHOSPHATE

Systematic Name

English

DTTP

Common Name

English

THYMIDINE 5'-TRIPHOSPHATE

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

206-669-7