Compounds > 5-iodo-2'-deoxyuridine 5'-monophosphate
Page last updated: 2024-09-27

5-iodo-2'-deoxyuridine 5'-monophosphate

Description

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

Cross-References

ID SourceID
PubMed CID449489
CHEMBL ID1160594
SCHEMBL ID285181
MeSH IDM0157451

Synonyms (17)

Synonym
idump
1-{(4s,2r,5r)-4-hydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-5-iodo-1,3-dihydropyrimidine-2,4-dione
[(2r,3s,5r)-3-hydroxy-5-(5-iodo-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
DB02324
5IU ,
5-iodo-2'-deoxyuridine-5'-monophosphate
iododeoxyuridylate
[(2r,3s,5r)-3-hydroxy-5-(5-iodo-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate
2'-deoxy-5-iodouridine 5'-(dihydrogen phosphate)
1763-02-6
CHEMBL1160594 ,
5-iodo-dump
5-iodo-2'-deoxyuridine 5'-monophosphate
SCHEMBL285181
bdbm50010242
((2r,3s,5r)-3-hydroxy-5-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate
PD060159

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidylate synthaseLacticaseibacillus caseiKi1.60000.01001.65509.3900AID1134942; AID1147592
Thymidylate synthaseMus musculus (house mouse)Ki7.33500.00341.73759.3000AID228251; AID228252
Delta-type opioid receptorRattus norvegicus (Norway rat)Ki1.60000.00000.60689.2330AID1134942
Mu-type opioid receptorRattus norvegicus (Norway rat)Ki1.60000.00000.38458.6000AID1134942
Kappa-type opioid receptorRattus norvegicus (Norway rat)Ki1.60000.00000.18683.9500AID1134942
[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 synthaseLacticaseibacillus caseiKm1.44001.44004.33505.7000AID1147595
Thymidylate kinaseMycobacterium tuberculosis H37RvKm140.00004.50004.50004.5000AID211051; AID211056
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID87827Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain G1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID233940Ratio between Ki of L1210-P enzyme and Michaelis-Menten constant (kM)2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
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.
AID216539Evaluation of antiviral activity against Vesicular stomatitis virus.1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
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.
AID220992Evaluation of antitumor activity against thymidine kinase deficient Raji cell line1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
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.
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.
AID98532Evaluation of cytostatic activity by using antitumor assays against murine leukemia L1210 cells1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID87507Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain KOS.1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID1147596Activity at amethopterin-resistant Lactobacillus casei thymidylate synthetase assessed as rate of dTMP formation by absorbance 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.
AID98529Evaluation of antitumor activity against mutant murine leukemia L1210 cells1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID1147595Activity at amethopterin-resistant Lactobacillus casei thymidylate synthetase assessed as dTMP formation by absorbance 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.
AID228252Time-independent inhibition of thymidylate synthase from parenteral L1210 cells2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID218132Evaluation of antiviral activity against Vaccinia virus1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID233942Ratio between Ki of L1210-R enzyme and Michaelis-Menten constant (kM)2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID87508Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain McIntyre1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID87506Evaluation of antiviral activity against Herpes simplex virus type 1 (HSV-1) strain F1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
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.
AID87826Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain 196.1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID228251Time-independent inhibition of thymidylate synthase from FdUrd-resistant L1210 cells2000Journal of medicinal chemistry, Nov-30, Volume: 43, Issue:24
5-Substituted N(4)-hydroxy-2'-deoxycytidines and their 5'-monophosphates: synthesis, conformation, interaction with tumor thymidylate synthase, and in vitro antitumor activity.
AID221339Evaluation for antitumor activity against human lymphoblast Raji cells1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID228417Compound was evaluated for the inhibition of L1210 thymidylate synthetase (L1210 dTMP)1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
AID1134942Competitive inhibition of thymidylate synthase purified from methotrexate-resistant Lactobacillus casei using 2'-deoxy[5-3H]uridine 5'-phosphate by radioisotope assay1979Journal of medicinal chemistry, Sep, Volume: 22, Issue:9
5-Cyano-2'-deoxyuridine 5'-phosphate: a potent competitive inhibitor of thymidylate synthetase.
AID87828Evaluation of antiviral activity against Herpes simplex virus type 2 (HSV-2) strain Lyons1986Journal of medicinal chemistry, Jul, Volume: 29, Issue:7
Synthesis and antitumor and antiviral properties of 5-halo- and 5-(trifluoromethyl)-2'-deoxyuridine 3',5'-cyclic monophosphates and neutral triesters.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (30.77)18.7374
1990's3 (23.08)18.2507
2000's6 (46.15)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
fluorodeoxyuridylate[no description available]medium90pyrimidine 2'-deoxyribonucleoside 5'-monophosphate
bromodeoxyuridylate[no description available]medium80
5-nitro-2'-deoxyuridine 5'-monophosphate[no description available]medium10
5-trifluoromethyl-2'-deoxyuridylic acid[no description available]medium30
5-chloro-2'-deoxyuridine 5'-triphosphate[no description available]medium30
thymidine monophosphate[no description available]medium60thymidine 5'-monophosphatefundamental metabolite
2'-deoxyuridylic acid[no description available]medium40deoxyuridine phosphate;
pyrimidine 2'-deoxyribonucleoside 5'-monophosphate		Escherichia coli metabolite;
metabolite;
mouse metabolite
floxuridine[no description available]medium20nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
idoxuridine[no description available]medium40organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
bromodeoxyuridine[no description available]medium20pyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
trifluridine[no description available]medium20nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
EC 2.1.1.45 (thymidylate synthase) inhibitor
5-chloro-2'-deoxyuridine[no description available]medium20
brivudine[no description available]medium10
5-(2-bromovinyl)-2'-deoxyuridylate[no description available]medium10
5-hydroxymethyl-2'-deoxyuridine[no description available]medium10pyrimidine 2'-deoxyribonucleoside
n-4-hydroxy-2'-deoxycytidylic acid[no description available]medium10
3'-azido-3'-deoxythymidine 5'phosphate[no description available]medium20
3'-amino-3'-deoxythymidine 5'-monophosphate[no description available]medium20
thymidine[no description available]medium20pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
5-fluorouridine[no description available]medium10organofluorine compound;
uridines		mutagen
doxifluridine[no description available]medium10organofluorine compound;
pyrimidine 5'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
prodrug
alovudine[no description available]medium10pyrimidine 2',3'-dideoxyribonucleoside
zidovudine[no description available]medium10azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
thymine arabinoside[no description available]medium10N-glycosyl compound
5'-amino-2',5'-dideoxythymidine[no description available]medium10
edoxudin[no description available]medium10pyrimidine 2'-deoxyribonucleoside
3'-amino-2',3'-dideoxythymidine[no description available]medium10
2'-fluorothymidine[no description available]medium10
adenosine diphosphate[no description available]medium10adenosine 5'-phosphate;
purine ribonucleoside 5'-diphosphate		fundamental metabolite;
human metabolite
5,10-methylenetetrahydrofolic acid[no description available]medium10benzamides;
methylenetetrahydrofolic acid
ConditionIndicatedRelationship StrengthStudiesTrials
Germinoblastoma0low10
Kaposi Sarcoma0low10
Kaposi's Sarcoma0low10
Leukemia L 12100low10
Leukemia L12100low10
Lymphoma0low10
Lymphoma, Malignant0low10
Multiple Idiopathic Pigmented Hemangiosarcoma0low10
Reticulolymphosarcoma0low10
Sarcoma, Germinoblastic0low10
Sarcoma, Kaposi0low10

Research Highlights

Bioavailability (1)

ArticleYear
Specific targeting of the antiviral drug 5-iodo 2'-deoxyuridine to the parenchymal liver cell using lactosylated poly-L-lysine.
Journal of hepatology, Volume: 21, Issue: 5		1994
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]