Page last updated: 2024-11-06

2'-deoxyuridylic acid

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

Description

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

Cross-References

ID SourceID
PubMed CID65063
CHEMBL ID211312
CHEBI ID17622
SCHEMBL ID8200
MeSH IDM0050351

Synonyms (50)

Synonym
CHEBI:17622 ,
deoxyuridylate
2'-deoxyuridine-5'-monophosphate
2'-deoxyuridine 5'-monophosphate
1-{(4s,2r,5r)-4-hydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1,3-dihydropyrimidine-2,4-dione
deoxy-ump
uridine, 2'-deoxy-, 5'-(dihydrogen phosphate)
deoxyuridine 5'-monophosphate
2,4(1h,3h)-pyrimidinedione, 1-(2-deoxy-5-o-phosphono-beta-d-erythro-pentofuranosyl)-
2'-deoxyuridylate
uridine, 2'-deoxy-, 5'-phosphate
5'-uridylic acid, 2'-deoxy-
C00365
964-26-1
deoxyuridine 5'-phosphate
2'-deoxyuridine 5'-phosphate
2'-deoxy-5'-uridylic acid
2'-deoxyuridylic acid
DUMP ,
deoxyuridylic acid
deoxyuridine monophosphate
1TSV
1JMG
1JMI
DB03800
1NJB
1NJD
1TSY
1JMF
1BP0
brn 0042143
einecs 213-518-9
2''-deoxy-5''-uridylic acid
bdbm50186267
CHEMBL211312 ,
2'-deoxyuridinemonophosphate
[(2r,3s,5r)-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
2''-deoxyuridinemonophosphate
bdbm50028108
phosphoric acid mono-[5-(2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester
n9j10kfg94 ,
unii-n9j10kfg94
SCHEMBL8200
{[(2r,3s,5r)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
DTXSID20242223
2'-deoxy-5'-uridylate
((2r,3s,5r)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
2'-deoxyuridine-5'-phosphate
2'-deoxy-5'-ump
Q2741362

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Previous drug design efforts based on co-factor analogues have produced good inhibitors of TS, but poor bioavailability and toxicity have limited their usefulness."( The complex of the anti-cancer therapeutic, BW1843U89, with thymidylate synthase at 2.0 A resolution: implications for a new mode of inhibition.
Stout, TJ; Stroud, RM, 1996
)
0.29
" Further research is needed to clarify the role of choline and methionine concentration and the importance of the reduced folate carrier and the folate receptor in determining the relative bioavailability of 5-MeTHF and FA with regard to genome stability."( A comparison of folic acid and 5-methyltetrahydrofolate for prevention of DNA damage and cell death in human lymphocytes in vitro.
Fenech, M; Wang, X, 2003
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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
deoxyuridine phosphate
pyrimidine 2'-deoxyribonucleoside 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 + dUMP = ADP + dUDP ( 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 (20)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidylate synthaseLacticaseibacillus caseiKi2.26000.01001.65509.3900AID1147594
Thymidylate synthaseHomo sapiens (human)Ki3.00000.00010.34353.0000AID212456
Thymidylate synthaseMus musculus (house mouse)Ki6.50000.00341.73759.3000AID1136575
Gonadotropin-releasing hormone receptorRattus norvegicus (Norway rat)Ki6.50000.00383.51866.5000AID1136575
Thymidylate synthase Bos taurus (cattle)Ki8.00008.00008.00008.0000AID1136574
[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, Protein (thymidylate Synthase)Lacticaseibacillus caseiKd4.00004.00004.00004.0000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd1.14000.85001.14001.7000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd1.14000.85001.14001.7000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd1.14000.85001.14001.7000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd2.15000.490033.5180160.0000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd2.15000.490033.5180160.0000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd2.15000.490033.5180160.0000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd2.15000.490033.5180160.0000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd2.15000.490033.5180160.0000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd13.500011.000013.500016.0000AID977611
Chain A, Thymidylate SynthaseLacticaseibacillus caseiKd13.500011.000013.500016.0000AID977611
[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)
Thymidylate synthase Escherichia coliKm2.00002.00002.00002.0000AID220357
Thymidylate synthaseLacticaseibacillus caseiKm5.10001.44004.33505.7000AID1147593; AID220358
Thymidylate synthaseHomo sapiens (human)Km5.25005.25005.25005.2500AID328152
Thymidylate kinaseHomo sapiens (human)Km170.00005.00007.725010.0000AID553325
Thymidylate kinaseMycobacterium tuberculosis H37RvKm2,100.00004.50004.50004.5000AID211051; AID211056
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (29)

Processvia Protein(s)Taxonomy
dTMP biosynthetic processThymidylate synthaseHomo sapiens (human)
dTTP biosynthetic processThymidylate synthaseHomo sapiens (human)
circadian rhythmThymidylate synthaseHomo sapiens (human)
response to xenobiotic stimulusThymidylate synthaseHomo sapiens (human)
response to toxic substanceThymidylate synthaseHomo sapiens (human)
negative regulation of translationThymidylate synthaseHomo sapiens (human)
uracil metabolic processThymidylate synthaseHomo sapiens (human)
methylationThymidylate synthaseHomo sapiens (human)
response to progesteroneThymidylate synthaseHomo sapiens (human)
response to vitamin AThymidylate synthaseHomo sapiens (human)
response to cytokineThymidylate synthaseHomo sapiens (human)
tetrahydrofolate interconversionThymidylate synthaseHomo sapiens (human)
response to ethanolThymidylate synthaseHomo sapiens (human)
response to organophosphorusThymidylate synthaseHomo sapiens (human)
developmental growthThymidylate synthaseHomo sapiens (human)
cartilage developmentThymidylate synthaseHomo sapiens (human)
response to glucocorticoidThymidylate synthaseHomo sapiens (human)
response to folic acidThymidylate synthaseHomo sapiens (human)
intestinal epithelial cell maturationThymidylate synthaseHomo sapiens (human)
DNA biosynthetic processThymidylate synthaseHomo sapiens (human)
liver regenerationThymidylate synthaseHomo 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)
dTTP biosynthetic processThymidylate synthase Bos taurus (cattle)
methylationThymidylate synthase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
mRNA regulatory element binding translation repressor activityThymidylate synthaseHomo sapiens (human)
thymidylate synthase activityThymidylate synthaseHomo sapiens (human)
folic acid bindingThymidylate synthaseHomo sapiens (human)
protein homodimerization activityThymidylate synthaseHomo sapiens (human)
sequence-specific mRNA bindingThymidylate synthaseHomo 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 (6)

Processvia Protein(s)Taxonomy
nucleusThymidylate synthaseHomo sapiens (human)
cytoplasmThymidylate synthaseHomo sapiens (human)
mitochondrionThymidylate synthaseHomo sapiens (human)
mitochondrial inner membraneThymidylate synthaseHomo sapiens (human)
mitochondrial matrixThymidylate synthaseHomo sapiens (human)
cytosolThymidylate synthaseHomo sapiens (human)
mitochondrionThymidylate synthaseHomo sapiens (human)
cytosolThymidylate synthaseHomo sapiens (human)
mitochondrial matrixThymidylate kinaseHomo sapiens (human)
cytosolThymidylate kinaseHomo sapiens (human)
mitochondrionThymidylate kinaseHomo sapiens (human)
nucleusThymidylate kinaseHomo sapiens (human)
cytoplasmThymidylate kinaseHomo sapiens (human)
nucleusThymidylate synthase Bos taurus (cattle)
cytoplasmThymidylate synthase Bos taurus (cattle)
mitochondrionThymidylate synthase Bos taurus (cattle)
mitochondrial inner membraneThymidylate synthase Bos taurus (cattle)
mitochondrial matrixThymidylate synthase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (29)

Assay IDTitleYearJournalArticle
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB1996Biochemistry, Apr-23, Volume: 35, Issue:16
Partitioning roles of side chains in affinity, orientation, and catalysis with structures for mutant complexes: asparagine-229 in thymidylate synthase.
AID1811Experimentally measured binding affinity data derived from PDB1996Biochemistry, Apr-23, Volume: 35, Issue:16
Partitioning roles of side chains in affinity, orientation, and catalysis with structures for mutant complexes: asparagine-229 in thymidylate synthase.
AID1811Experimentally measured binding affinity data derived from PDB1998Journal of molecular biology, Feb-13, Volume: 276, Issue:1
Contributions of orientation and hydrogen bonding to catalysis in Asn229 mutants of thymidylate synthase.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB1998Journal of molecular biology, Feb-13, Volume: 276, Issue:1
Contributions of orientation and hydrogen bonding to catalysis in Asn229 mutants of thymidylate synthase.
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.
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.
AID211054Kinetic 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.
AID1136575Competitive inhibition of purified mouse Ehrlich ascites tumor cell thymidylate synthetase using 5-[3H]-2'-deoxyuridine 5'-phosphate as substrate after 7 mins by double reciprocal plot method1977Journal of medicinal chemistry, May, Volume: 20, Issue:5
Thymidylate synthetase inhibitors. Synthesis of N-substituted 5-aminomethyl-2'-deoxyuridine 5'-phosphates.
AID1147593Activity at amethopterin-resistant Lactobacillus casei thymidylate synthetase 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.
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.
AID220357Compound was evaluated for the inhibition of dTMP synthetase with respect to dUMP.1981Journal of medicinal chemistry, Oct, Volume: 24, Issue:10
Interaction of 1-(5-phospho-beta-D-arabinofuranosyl)-5-substituted-uracils with thymidylate synthetase: mechanism-based inhibition by 1-(5-phospho-beta-D-arabinosyl)-5-fluorouracil.
AID328152Activity at human recombinant thymidylate synthase2008Bioorganic & medicinal chemistry letters, Apr-15, Volume: 18, Issue:8
A molecular modeling study of the interaction of 2'-fluoro-substituted analogues of dUMP/FdUMP with thymidylate synthase.
AID220358The compound was evaluated for the inhibition of dTMP synthetase from Lactobacillus casei1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Inhibition of thymidylate synthetase by 5-alkynyl-2'-deoxyuridylates.
AID220367The apparent association constant (Ki) with dTMP synthetase enzyme from chick embryo in the absence of CH2-H4 folate was evaluated using conventional spectrophotometric assay; Active1984Journal of medicinal chemistry, Oct, Volume: 27, Issue:10
Interaction of N4-hydroxy-2'-deoxycytidylic acid with thymidylate synthetase.
AID99552Inhibition of dTMP synthetase in the absence of CH2-H4 folate Lactobacillus casei1983Journal of medicinal chemistry, Aug, Volume: 26, Issue:8
Mechanism of action of 2',5-difluoro-1-arabinosyluracil.
AID266613Inhibition of Trypanosoma cruzi dUTPase at 1 mM2006Bioorganic & medicinal chemistry letters, Jul-15, Volume: 16, Issue:14
Design, synthesis and evaluation of novel uracil amino acid conjugates for the inhibition of Trypanosoma cruzi dUTPase.
AID1136574Competitive inhibition of purified calf thymus thymidylate synthetase using 5-[3H]-2'-deoxyuridine 5'-phosphate as substrate after 7 mins by double reciprocal plot method1977Journal of medicinal chemistry, May, Volume: 20, Issue:5
Thymidylate synthetase inhibitors. Synthesis of N-substituted 5-aminomethyl-2'-deoxyuridine 5'-phosphates.
AID212456Inhibitory activity against human thymidylate synthase with variable concentration of dUMP and fixed N5,10-CH2-H4PteGlu (200 uM)1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
A potent multisubstrate analogue inhibitor of human thymidylate synthetase.
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.
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.
AID74254Inhibitory concentration at which there is accumulation of UDP-[3H]-GlcNAc in the lumen of the Golgi membranes; Not determined1996Journal of medicinal chemistry, Jul-19, Volume: 39, Issue:15
Inhibition of UDP-N-acetylglucosamine import into Golgi membranes by nucleoside monophosphates.
AID211051Affinity 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.
AID1136573Competitive inhibition of purified Escherichia coli thymidylate synthetase using t5-[3H]-2'-deoxyuridine 5'-phosphate as substrate after 7 mins by double reciprocal plot method1977Journal of medicinal chemistry, May, Volume: 20, Issue:5
Thymidylate synthetase inhibitors. Synthesis of N-substituted 5-aminomethyl-2'-deoxyuridine 5'-phosphates.
AID212821The rate constant in Acetonitrile and buffered aqueous acetonitrile solution, at 30 degrees C and pH 6.81986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
Thiol addition to quinones: model reactions for the inactivation of thymidylate synthase by 5-p-benzoquinonyl-2'-deoxyuridine 5'-phosphate.
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.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2000Biochemistry, Feb-08, Volume: 39, Issue:5
Energetic contributions of four arginines to phosphate-binding in thymidylate synthase are more than additive and depend on optimization of "effective charge balance".
AID1811Experimentally measured binding affinity data derived from PDB2000Biochemistry, Feb-08, Volume: 39, Issue:5
Energetic contributions of four arginines to phosphate-binding in thymidylate synthase are more than additive and depend on optimization of "effective charge balance".
AID1811Experimentally measured binding affinity data derived from PDB1996Protein engineering, Jan, Volume: 9, Issue:1
Contribution of a salt bridge to binding affinity and dUMP orientation to catalytic rate: mutation of a substrate-binding arginine in thymidylate synthase.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB1996Protein engineering, Jan, Volume: 9, Issue:1
Contribution of a salt bridge to binding affinity and dUMP orientation to catalytic rate: mutation of a substrate-binding arginine in thymidylate synthase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (238)

TimeframeStudies, This Drug (%)All Drugs %
pre-199061 (25.63)18.7374
1990's75 (31.51)18.2507
2000's61 (25.63)29.6817
2010's37 (15.55)24.3611
2020's4 (1.68)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.97

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 Index8.97 (24.57)
Research Supply Index5.49 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.97)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews7 (2.90%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other234 (97.10%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]