Page last updated: 2024-12-05

thymidine monophosphate

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Description

Thymidine monophosphate (TMP) is a nucleotide that serves as a building block for DNA. It is composed of the nucleobase thymine, the sugar deoxyribose, and a phosphate group. TMP is synthesized from deoxyribose-1-phosphate and thymine via the action of the enzyme thymidylate synthase. TMP is essential for DNA replication and repair, and its deficiency can lead to various genetic diseases. Research into TMP focuses on understanding its role in DNA metabolism, exploring potential therapeutic applications, and investigating the mechanisms underlying its regulation and function. '

Thymidine Monophosphate: 5-Thymidylic acid. A thymine nucleotide containing one phosphate group esterified to the deoxyribose moiety. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dTMP : The neutral species of thymidine 5'-monophosphate (2'-deoxythymidine 5'-monophosphate). [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]

Cross-References

ID SourceID
PubMed CID9700
CHEMBL ID394429
CHEBI ID17013
SCHEMBL ID21257
MeSH IDM0021450

Synonyms (64)

Synonym
thymidine-5''-monophosphate
bdbm50332929
((2r,3s,5r)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-tetrahydrofuran-2-yl)methyl dihydrogen phosphate
thymidine-5''-phosphate
(r)-1-((4s,5r)-4-hydroxy-5-methylphosphate-tetrahydro-furan-2-yl)-5-methyl-1h-pyrimidine-2,4-dione
2''-deoxythymidine monophosphate
phosphoric acid mono-[3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester
(dt)1
thymidine-5'-monophosphoric acid
thymidine-5'-phosphate
ribothymidine 5'-monophosphate
2'-deoxy-5-methyluridine 5'-(dihydrogen phosphate)
CHEBI:17013 ,
thymidine 5'-(dihydrogen phosphate)
5-methyl-dump
thymidine, mono(dihydrogen phosphate) (ester)
thymidine phosphate
thymidine mononucleotide
thymidine 5'-phosphoric acid
tmp (nucleotide)
5'-tmp
2'-deoxythymidine 5'-monophosphate
deoxyribosylthymine monophosphate
deoxy tmp
5'-dtmp
tmp (van)
5'-thymidylic acid (8ci,9ci)
deoxythymidine monophosphate
deoxythymidine 5'-monophosphate
deoxythymidine phosphate
5'-thymidylic acid
thymidylic acid
365-07-1
deoxythymidylic acid
C00364
thymidine monophosphate
thymidine 5'-phosphate
deoxythymidine 5'-phosphate
thymidylate
dtmp
[(2r,3s,5r)-3-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
thymidine-5'-monophosphate
1TYS
DB01643
nsc 46713
deoxythymydilic acid
CHEMBL394429 ,
2'-deoxythymidine monophosphate
[(2r,3s,5r)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate
BMSE000296
43w3021x6c ,
unii-43w3021x6c
EPITOPE ID:196259
SCHEMBL21257
qbt ,
{[(2r,3s,5r)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid
5-thymidylic acid
deoxythymydilate
thymidine 5'-phosphorate
5'-thymidylate
thymidine-5'-monophosphorate
((2r,3s,5r)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate
DTXSID60904171
Q23905769

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Acute toxicity studies have shown that WHI-05 has no detectable adverse effects on laboratory animals."( Evaluation of subchronic (13 weeks) and reproductive toxicity potential of intravaginal gel-microemulsion formulation of a dual-function phenyl phosphate derivative of bromo-methoxy zidovudine (compound WHI-05) in B(6)C(3)F(1) mice.
D'Cruz, OJ; Uckun, FM; Waurzyniak, B; Yiv, SH, 2000
)
0.31
" In vivo toxicity studies in non-human primates and rodents given WHI-07 (20 mg kg(-1)) intravenously and intraperitonealy, respectively, had no detectable adverse effects on hematological and clinical chemistry profiles."( Evaluation of subchronic (13-week) and reproductive toxicity potential of intravaginal gel-microemulsion formulation of a dual-function phenyl phosphate derivative of bromo-methoxy zidovudine (compound whi-07) in B(6)C(3)F(1) mice.
D'Cruz, OJ; Uckun, FM; Waurzyniak, B; Yiv, SH,
)
0.13
" Repeated intravaginal exposure of mice to WHI-07 for 13 weeks had no toxicologically significant effect on organ weights, and did not cause any adverse changes in hematology parameters or blood chemistry profiles."( Short-Term (13-week) toxicity study of 5-bromo-6-methoxy-5,6-dihydro-3'-azidothymidine-5'-(p-bromophenyl) methoxyalaninyl phosphate (WHI-07), a novel anti-HIV and contraceptive agent, in B6C3F1 mice.
D'Cruz, OJ; Uckun, FM, 2001
)
0.31
" Repeated intravaginal exposure of mice to 2% WHI-07 had no adverse effects on ovulation response, mean number of eggs recovered or the percentage of eggs fertilized or cleaved."( Lack of adverse effects on fertility of female CD-1 mice exposed to repetitive intravaginal gel-microemulsion formulation of a dual-function anti-HIV agent: aryl phosphate derivative of bromo-methoxy-zidovudine (compound WHI-07).
D'Cruz, OJ; Uckun, FM,
)
0.13
" WHI-07 has clinical potential as an active ingredient of a safe vaginal/rectal microbicide."( Two-year toxicity and carcinogenicity studies in B(6)C(3)F(1) mice with 5-bromo-6-methoxy-5,6-dihydro-3'-azidothymidine-5'-(p-bromophenyl) methoxyalaninyl phosphate (WHI-07), a novel anti-HIV and contraceptive agent.
D'Cruz, OJ; Erbeck, D; Uckun, FM; Waurzyniak, B, 2002
)
0.31
" No STAMP-related toxic lesions were found in any of the organs from STAMP-treated cats or dogs."( In vivo pharmacokinetics and toxicity profile of the anti-HIV agent stampidine in dogs and feline immunodeficiency virus-infected cats.
Erbeck, D; Tibbles, H; Uckun, FM; Venkatachalam, TK; Waurzyniak, B, 2006
)
0.33
" Rats administrated with multiple-doses of Nu-3 showed no visible toxic symptoms."( Acute, multiple-dose dermal and genetic toxicity of Nu-3: a novel antimicrobial agent.
Cao, S; Hu, Y; Sun, J; Sun, LQ; Wang, M; Zhang, G, 2010
)
0.36

Pharmacokinetics

ExcerptReferenceRelevance
" In accordance with its favorable pharmacokinetic profile and in vitro potency, STAMP exhibited dose-dependent and potent in vivo anti-HIV activity in Hu-PBL-SCID mice against a genotypically and phenotypically nucleoside analog reverse transcriptase inhibitor (NRTI)-resistant clinical HIV type 1 (HIV-1) isolate (BR/92/019; D67N, L214F, T215D, K219Q) at nontoxic dose levels."( In vivo toxicity, pharmacokinetics, and anti-human immunodeficiency virus activity of stavudine-5'-(p-bromophenyl methoxyalaninyl phosphate) (stampidine) in mice.
Chen, CL; Lisowski, E; Pendergrass, S; Qazi, S; Uckun, FM; Venkatachalam, TK; Waurzyniak, B, 2002
)
0.31

Compound-Compound Interactions

ExcerptReferenceRelevance
"The presence of low concentrations of the lipophilic dihydrofolate reductase inhibitors metoprine or trimetrexate, which cause little inhibition in the growth of cultured hepatoma cells in combination with weakly inhibiting concentrations of 5,10-dideazatetrahydrofolate, exhibit greater activity than would be predicted by the activity of the individual components."( Antifolate drug interactions: enhancement of growth inhibition due to the antipurine 5,10-dideazatetrahydrofolic acid by the lipophilic dihydrofolate reductase inhibitors metoprine and trimetrexate.
Boschelli, D; Galivan, J; Kerwar, SS; Nimec, Z; Oronsky, AL; Rhee, M, 1988
)
0.27

Dosage Studied

ExcerptRelevanceReference
" Dose-response curves resulting from experiments with up to 12 different inhibitor concentrations were analyzed by linear regression."( The function of DNA polymerases in DNA repair synthesis of ultraviolet-irradiated human fibroblasts.
Popanda, O; Thielmann, HW, 1992
)
0.28
"1-10 microM but the dose-response relationship was poor."( Phosphodiester amidates of allenic nucleoside analogues: anti-HIV activity and possible mechanism of action.
Maeda, Y; Mitsuya, H; Winter, H; Zemlicka, J, 1996
)
0.29
" When tested for their ability to alter cocaine discrimination, four of the analogs (three of which had N-substitutions and shallow dose-response curves as cocaine substitutes) actually enhanced cocaine discrimination, often at combined doses of cocaine and test compound that were inactive when given separately."( Biochemical and behavioral characterization of novel methylphenidate analogs.
Deutsch, HM; Holtzman, SG; Massey, AT; Schweri, MM, 2002
)
0.31
"A powerful statistical method was designed using JMP software to detect factors contributing to differences in the dissolution process of an antiviral drug delivered in an oral dosage form."( Evaluating dissolution profiles of an anti-HIV agent using ANOVA and non-linear regression models in JMP software.
Qazi, S; Samuel, NK; Uckun, FM; Venkatachalam, TK, 2003
)
0.32
" Genital tract histopathology was performed in the pig and rabbit at the end of dosing period but after 18 weeks post-dosing in the cat."( Preclinical evaluation of a dual-acting microbicidal prodrug WHI-07 in combination with vanadocene dithiocarbamate in the female reproductive tract of rabbit, pig, and cat.
D'Cruz, OJ; Uckun, FM, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
fundamental metaboliteAny metabolite produced by all living cells.
[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 (1)

ClassDescription
thymidine 5'-monophosphate
[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 (24)

PathwayProteinsCompounds
Pyrimidine Metabolism2353
beta-Ureidopropionase Deficiency2353
UMP Synthase Deficiency (Orotic Aciduria)2353
Dihydropyrimidinase Deficiency2353
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)2353
One Carbon Pool by Folate1227
Salvage Pathways of Pyrimidine Deoxyribonucleotides514
One Carbon Pool by Folate I527
Pyrimidine Deoxyribonucleosides Salvage815
Folate metabolism ( Folate metabolism )2039
Pyrimidine Nucleotides and Nucleosides metabolism ( Pyrimidine Nucleotides and Nucleosides metabolism )4549
ATP + dTMP = ADP + dTDP ( Pyrimidine Nucleotides and Nucleosides metabolism )14
Pyrimidine synthesis and deprivation pathway (COVID-19 Disease Maps)1329
folate metabolism022
purine and pyrimidine metabolism032
formylTHF biosynthesis II027
formylTHF biosynthesis I026
Trans-sulfuration and one-carbon metabolism020
Fluoropyrimidine activity015
One-carbon metabolism013
Trans-sulfuration, one-carbon metabolism and related pathways053
Biochemical pathways: part I0466
Ethanol effects on histone modifications017
Pyrimidine metabolism038
Disorders of folate metabolism and transport1827

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidylate synthaseLacticaseibacillus caseiKi12.09500.01001.65509.3900AID1147592; AID1147594
Thymidylate kinaseMycobacterium tuberculosis H37RvKi4.50004.50008.500010.0000AID545759
[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)
Chain A, Thymidylate SynthaseEscherichia coliKd3.27003.27003.27003.2700AID977611
[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)
Thymidine kinase, cytosolicHomo sapiens (human)Km5.00000.29002.27675.0000AID210900
Polyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)Km4.50000.16001.60674.5000AID281530
Thymidylate kinaseHomo sapiens (human)Km11.10005.00007.725010.0000AID281529; AID325367; AID553325
Thymidylate kinaseMycobacterium tuberculosis H37RvKm9.57144.50004.50004.5000AID210898; AID211050; AID211052; AID211056; AID239750; AID281530; AID302231
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (44)

Processvia Protein(s)Taxonomy
nucleobase-containing compound metabolic processThymidine kinase, cytosolicHomo sapiens (human)
deoxyribonucleoside monophosphate biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine metabolic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
protein homotetramerizationThymidine kinase, cytosolicHomo sapiens (human)
DNA synthesis involved in mitotic DNA replicationThymidine kinase, cytosolicHomo sapiens (human)
negative regulation of endothelial cell proliferationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukocyte chemotaxis involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukocyte migration involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene production involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene metabolic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
humoral immune responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of angiogenesisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
positive regulation of bone mineralizationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
dendritic cell migrationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
glucose homeostasisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
long-chain fatty acid biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of fat cell differentiationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of insulin secretionPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of vascular wound healingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of wound healingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of inflammatory response to woundingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of cytokine production involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of cellular response to oxidative stressPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene A4 biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of reactive oxygen species biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of response to endoplasmic reticulum stressPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of sprouting angiogenesisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
positive regulation of leukocyte adhesion to arterial endothelial cellPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipoxin biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
dTDP biosynthetic processThymidylate kinaseHomo sapiens (human)
dTTP biosynthetic processThymidylate kinaseHomo sapiens (human)
response to estrogenThymidylate kinaseHomo sapiens (human)
myoblast differentiationThymidylate kinaseHomo sapiens (human)
thymidine biosynthetic processThymidylate kinaseHomo sapiens (human)
response to cadmium ionThymidylate kinaseHomo sapiens (human)
nucleoside monophosphate phosphorylationThymidylate kinaseHomo sapiens (human)
cellular response to growth factor stimulusThymidylate kinaseHomo sapiens (human)
dUDP biosynthetic processThymidylate kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
thymidine kinase activityThymidine kinase, cytosolicHomo sapiens (human)
protein bindingThymidine kinase, cytosolicHomo sapiens (human)
ATP bindingThymidine kinase, cytosolicHomo sapiens (human)
zinc ion bindingThymidine kinase, cytosolicHomo sapiens (human)
identical protein bindingThymidine kinase, cytosolicHomo sapiens (human)
arachidonate 5-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonate 12(S)-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
iron ion bindingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
protein bindingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
hydrolase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
thymidylate kinase activityThymidylate kinaseHomo sapiens (human)
ATP bindingThymidylate kinaseHomo sapiens (human)
nucleoside diphosphate kinase activityThymidylate kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
nucleusThymidine kinase, cytosolicHomo sapiens (human)
cytosolThymidine kinase, cytosolicHomo sapiens (human)
extracellular regionPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
extracellular spacePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelopePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelope lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nucleoplasmPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
cytosolPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear matrixPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear membranePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
secretory granule lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
perinuclear region of cytoplasmPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
ficolin-1-rich granule lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelopePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
mitochondrial matrixThymidylate kinaseHomo sapiens (human)
cytosolThymidylate kinaseHomo sapiens (human)
mitochondrionThymidylate kinaseHomo sapiens (human)
nucleusThymidylate kinaseHomo sapiens (human)
cytoplasmThymidylate kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (37)

Assay IDTitleYearJournalArticle
AID211056Compound was tested for binding affinity against Mycobacterium tuberculosis thymidine monophosphate kinase2002Bioorganic & medicinal chemistry letters, Oct-07, Volume: 12, Issue:19
Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID100249Effect (10e-4 M) on DNA synthesis in mouse LM(TK-) cells blocked in DNA synthesis with Aminopterin1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Zwitterionic 3'-O-acyl derivatives of thymidine 5'-phosphate as potential sources of intracellular thymidine 5'-phosphate in cells in culture.
AID211050Affinity towards thymidine monophosphate kinase (TMPKmt) in Mycobacterium tuberculosis2003Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18
Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID281534Selectivity index, Ki for human TMPK/Ki for Mycobacterium tuberculosis TMPK2004Journal of medicinal chemistry, Dec-02, Volume: 47, Issue:25
Discovery of bicyclic thymidine analogues as selective and high-affinity inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase.
AID100250Effect (10e-5 M) on DNA synthesis in mouse LM(TK-) cells blocked in DNA synthesis with Aminopterin1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Zwitterionic 3'-O-acyl derivatives of thymidine 5'-phosphate as potential sources of intracellular thymidine 5'-phosphate in cells in culture.
AID1147592Inhibition of amethopterin-resistant Lactobacillus casei thymidylate synthetase-catalyzed dTMP formation using dUMP as substrate by spectrophotometric analysis in presence of CH2-H4-folate1977Journal of medicinal chemistry, Nov, Volume: 20, Issue:11
Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
AID1697902Antibacterial activity against Staphylococcus aureus ATCC 29213 assessed as reduction in bacterial growth after 16 hrs by broth microdilution method2020Journal of natural products, 10-23, Volume: 83, Issue:10
AID220368The apparent association constant (Ki) with dTMP synthetase enzyme from chick embryo in the absence of CH2-H4 folate was evaluated; Active1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Interaction of N4-hydroxy-2'-deoxycytidylic acid with thymidylate synthetase.
AID1697904Antibacterial activity against Micrococcus luteus SCSIO ML01 assessed as reduction in bacterial growth after 16 hrs by broth microdilution method2020Journal of natural products, 10-23, Volume: 83, Issue:10
AID1697903Antibacterial activity against Bacillus thuringiensis SCSIO BT01 assessed as reduction in bacterial growth after 16 hrs by broth microdilution method2020Journal of natural products, 10-23, Volume: 83, Issue:10
AID1200096Inhibition of Brugia malayi thymidylate kinase using dTMP substrate by spectrophotometric assay2015European journal of medicinal chemistry, Mar-26, Volume: 93Synthesis, molecular docking and Brugia malayi thymidylate kinase (BmTMK) enzyme inhibition study of novel derivatives of [6]-shogaol.
AID74255The compound was tested for extent of 1 uM UDP-[3H]-GlcNAc accumulation into the lumen of the Golgi membranes from rabbit liver homogenate1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID239750Km for mycobacterium tuberculosis thymidine monophosphate kinase2005Journal of medicinal chemistry, Apr-07, Volume: 48, Issue:7
LEA3D: a computer-aided ligand design for structure-based drug design.
AID1147594Inhibition of amethopterin-resistant Lactobacillus casei thymidylate synthetase-catalyzed 5-BrdUMP dehalogenation by absorbance analysis in absence of CH2-H4-folate1977Journal of medicinal chemistry, Nov, Volume: 20, Issue:11
Inhibition of Lactobacillus casei thymidylate synthetase by 5-substituted 2'-deoxyuridylates. Preliminary quantitative structure-activity relationship.
AID1697905Antibacterial activity against methicillin-resistant Bacillus subtilis 1064 assessed as reduction in bacterial growth after 16 hrs by broth microdilution method2020Journal of natural products, 10-23, Volume: 83, Issue:10
AID545759Inhibition of Mycobacterium tuberculosis Thymidine monophosphate kinase by spectrophotometry2010European journal of medicinal chemistry, Dec, Volume: 45, Issue:12
Design, synthesis and inhibitory activity against Mycobacterium tuberculosis thymidine monophosphate kinase of acyclic nucleoside analogues with a distal imidazoquinolinone.
AID211052Affinity towards thymidine monophosphate kinase (TMPKmt) in Mycobacterium tuberculosis using HPLC chromatography test2003Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18
Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID1697906Antibacterial activity against methicillin-resistant Staphylococcus aureus shhs-A1 assessed as reduction in bacterial growth after 16 hrs by broth microdilution method2020Journal of natural products, 10-23, Volume: 83, Issue:10
AID100248Effect (10e-3 M) on DNA synthesis in mouse LM(TK-) cells blocked in DNA synthesis with Aminopterin1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Zwitterionic 3'-O-acyl derivatives of thymidine 5'-phosphate as potential sources of intracellular thymidine 5'-phosphate in cells in culture.
AID325367Activity for human recombinant TMP kinase2007Antimicrobial agents and chemotherapy, May, Volume: 51, Issue:5
Comparison of the phosphorylation of 4'-ethynyl 2',3'-dihydro-3'-deoxythymidine with that of other anti-human immunodeficiency virus thymidine analogs.
AID553325Activity at human recombinant TMPK by Michaelis-Menten equation analysis2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates.
AID235818ratio of Km (Km TMPKh / Km TMPKmt) was determined2003Journal of medicinal chemistry, Aug-28, Volume: 46, Issue:18
3'-C-branched-chain-substituted nucleosides and nucleotides as potent inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase.
AID302231Inhibition of Mycobacterium tuberculosis TMPK expressed in Escherichia coli by spectrophotometric assay2007Journal of medicinal chemistry, Nov-01, Volume: 50, Issue:22
Rational design of 5'-thiourea-substituted alpha-thymidine analogues as thymidine monophosphate kinase inhibitors capable of inhibiting mycobacterial growth.
AID302232Inhibition of human TMPK expressed in Escherichia coli by spectrophotometric assay2007Journal of medicinal chemistry, Nov-01, Volume: 50, Issue:22
Rational design of 5'-thiourea-substituted alpha-thymidine analogues as thymidine monophosphate kinase inhibitors capable of inhibiting mycobacterial growth.
AID74259In vitro inhibition of UDP-[3H]-GlcNAc import into the lumen of the Golgi membranes from rabbit liver homogenate.1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID210900In Vitro inhibition of Thymidine Monophosphatase Kinase (TMPKh)2003Journal of medicinal chemistry, Aug-28, Volume: 46, Issue:18
3'-C-branched-chain-substituted nucleosides and nucleotides as potent inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase.
AID211053Kinetic parameter Vm of thymidine monophosphate kinase (TMPKmt) in Mycobacterium tuberculosis was determined2003Bioorganic & medicinal chemistry letters, Sep-15, Volume: 13, Issue:18
Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID553326Ratio of kcat/km for human recombinant TMPK by Michaelis-Menten equation analysis2011Journal of medicinal chemistry, Jan-13, Volume: 54, Issue:1
Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates.
AID281529Inhibition of human TMPK by coupled spectrophotometric assay2004Journal of medicinal chemistry, Dec-02, Volume: 47, Issue:25
Discovery of bicyclic thymidine analogues as selective and high-affinity inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase.
AID210898In Vitro inhibition of Thymidine Monophosphatase Kinase of Mycobacterium tuberculosis (TMPKm)2003Journal of medicinal chemistry, Aug-28, Volume: 46, Issue:18
3'-C-branched-chain-substituted nucleosides and nucleotides as potent inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase.
AID325368Ratio of Kcat to Km of human recombinant TMPK relative to D4TDP2007Antimicrobial agents and chemotherapy, May, Volume: 51, Issue:5
Comparison of the phosphorylation of 4'-ethynyl 2',3'-dihydro-3'-deoxythymidine with that of other anti-human immunodeficiency virus thymidine analogs.
AID74253Inhibitory concentration at which there is accumulation of UDP-[3H]-GlcNAc in the lumen of the Golgi membranes.1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID211057Enzyme Kinetic constant was determined in the presence of Mycobacterium tuberculosis thymidine monophosphate kinase2002Bioorganic & medicinal chemistry letters, Oct-07, Volume: 12, Issue:19
Synthesis and evaluation of thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.
AID281530Inhibition of Mycobacterium tuberculosis TMPK by coupled spectrophotometric assay2004Journal of medicinal chemistry, Dec-02, Volume: 47, Issue:25
Discovery of bicyclic thymidine analogues as selective and high-affinity inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase.
AID26831Evaluated for the second dissociation constant1990Journal of medicinal chemistry, Apr, Volume: 33, Issue:4
Acyclic purine phosphonate analogues as antiviral agents. Synthesis and structure-activity relationships.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB1994Biochemistry, Feb-15, Volume: 33, Issue:6
Water-mediated substrate/product discrimination: the product complex of thymidylate synthase at 1.83 A.
AID1811Experimentally measured binding affinity data derived from PDB1994Biochemistry, Feb-15, Volume: 33, Issue:6
Water-mediated substrate/product discrimination: the product complex of thymidylate synthase at 1.83 A.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (665)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990266 (40.00)18.7374
1990's115 (17.29)18.2507
2000's172 (25.86)29.6817
2010's89 (13.38)24.3611
2020's23 (3.46)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 91.07

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index91.07 (24.57)
Research Supply Index6.55 (2.92)
Research Growth Index4.40 (4.65)
Search Engine Demand Index164.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (91.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.14%)5.53%
Reviews35 (5.04%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other658 (94.81%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]