Compounds > 6-azauridine-5'-monophosphate
Page last updated: 2024-11-07

6-azauridine-5'-monophosphate

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Description

6-azauridine-5'-monophosphate: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

6-azauridine 5'-monophosphate : A N-glycosyl-1,2,4-triazine that is the 6-aza analogue of uridine 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 CID150959
CHEMBL ID463480
CHEBI ID46319
SCHEMBL ID3214622
MeSH IDM0057949

Synonyms (35)

Synonym
6-azauridine 5'mp
nsc47549
aza ump
[(2r,3s,4r,5r)-5-(3,5-dioxo-1,2,4-triazin-2-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
6-azauridine 5'm
6-aza uridine 5'-monophosphate
up6 ,
{[(2r,3s,4r,5r)-5-(3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazin-2-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
bdbm21340
c6-uridine derivative, 18
6-aza-ump
1LOS ,
6-azauridine-5'-monophosphate
6-aza-uridine monophosphate
DB03718
[(2r,3s,4r,5r)-5-(3,5-dioxo-1,2,4-triazin-2-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
CHEMBL463480
2018-19-1
6-azauridine-5'-phosphate
SCHEMBL3214622
6-azauridine-5-monophosphate
W-201761
6-azauridine 5'-phosphoric acid
2-(5-o-phosphono-beta-d-ribofuranosyl)-1,2,4-triazine-3,5(2h,4h)-dione
Q27466936
((2r,3s,4r,5r)-5-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
5-hydroxy-2-(5-o-phosphonopentofuranosyl)-1,2,4-triazin-3(2h)-one
DTXSID60942235
((2r,3s,4r,5r)-5-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyldihydrogenphosphate
6-azaump
[(2r,3s,4r,5r)-5-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate
CHEBI:46319
6-aza ump
6-azauridine 5'-monophosphate
PD059502
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
EC 4.1.1.23 (orotidine-5'-phosphate decarboxylase) inhibitorAny EC 4.1.1.* (carboxy-lyase) inhibitor that interferes with the action of orotidine-5'-phosphate decarboxylase (EC 4.1.1.23).
[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
N-glycosyl-1,2,4-triazine
nucleoside monophosphate analogue
[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 Targets (9)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, orotidine 5'-monophosphate decarboxylaseMethanothermobacter thermautotrophicus str. Delta HKi0.06400.000050.1185200.0000AID977610
Chain B, orotidine 5'-monophosphate decarboxylaseMethanothermobacter thermautotrophicus str. Delta HKi0.06400.000050.1185200.0000AID977610
Chain A, orotidine 5'-monophosphate decarboxylaseArchaeaKi0.06400.000050.1185200.0000AID977610
Chain A, orotidine monophosphate decarboxylaseMethanothermobacter thermautotrophicusKi0.06400.000050.1185200.0000AID977610
Chain A, orotidine monophosphate decarboxylaseMethanothermobacter thermautotrophicus str. Delta HKi0.06400.000050.1185200.0000AID977610
Chain B, orotidine monophosphate decarboxylaseMethanothermobacter thermautotrophicus str. Delta HKi0.06400.000050.1185200.0000AID977610
Orotidine 5'-phosphate decarboxylaseMethanothermobacter thermautotrophicus str. Delta HKi8.63331.10003.65006.2000AID1798071; AID268966
Orotidine 5'-phosphate decarboxylaseSaccharomyces cerevisiae S288CKi0.06400.00000.03200.0640AID268967
Orotidine 5'-phosphate decarboxylase Plasmodium falciparum (malaria parasite P. falciparum)Ki1.00001.00001.00001.0000AID268968
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID393536Antitumor activity against human PC3 cells up to 50 uM after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393517Antitumor activity against human OCI-LY7 cells after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID268967Inhibition of Saccharomyces cerevisiae ODCase at 25 degreeC by competitive binding assay2006Journal of medicinal chemistry, Aug-10, Volume: 49, Issue:16
Design of inhibitors of orotidine monophosphate decarboxylase using bioisosteric replacement and determination of inhibition kinetics.
AID393534Antitumor activity against human T47D cells up to 50 uM after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393522Antitumor activity against human MDA468 cells after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393527Antitumor activity against human MDA468 cells up to 50 uM after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393524Antitumor activity against human COLO205 cells after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393532Antitumor activity against human Hs 578T cells up to 50 uM after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID312888Inhibition of Plasmodium falciparum ODCase2008Journal of medicinal chemistry, Feb-14, Volume: 51, Issue:3
Structure-activity relationships of C6-uridine derivatives targeting plasmodia orotidine monophosphate decarboxylase.
AID393526Antitumor activity against human MCF7 cells up to 50 uM after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID312889Inhibition of Plasmodium vivax ODCase2008Journal of medicinal chemistry, Feb-14, Volume: 51, Issue:3
Structure-activity relationships of C6-uridine derivatives targeting plasmodia orotidine monophosphate decarboxylase.
AID268968Inhibition of Plasmodium falciparum ODCase at 25 degreeC by competitive binding assay2006Journal of medicinal chemistry, Aug-10, Volume: 49, Issue:16
Design of inhibitors of orotidine monophosphate decarboxylase using bioisosteric replacement and determination of inhibition kinetics.
AID393523Antitumor activity against human OVCAR4 cells after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID312887Inhibition of Methanobacterium thermoautotrophicum ODCase2008Journal of medicinal chemistry, Feb-14, Volume: 51, Issue:3
Structure-activity relationships of C6-uridine derivatives targeting plasmodia orotidine monophosphate decarboxylase.
AID268966Inhibition of Methanobacterium thermoautotrophicum ODCase at 55 degreeC by competitive binding assay2006Journal of medicinal chemistry, Aug-10, Volume: 49, Issue:16
Design of inhibitors of orotidine monophosphate decarboxylase using bioisosteric replacement and determination of inhibition kinetics.
AID393515Antitumor activity against human OCI-AML1 cells after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393538Antitumor activity against human SNB19 cells up to 50 uM after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393519Antitumor activity against human SKW3 cells after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393516Antitumor activity against human OCI-AML2 cells after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393530Cytotoxicity against human CCD-967 cells up to 50 uM after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393520Antitumor activity against human MCF7 cells after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393521Antitumor activity against human LOX cells after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID393518Antitumor activity against human OCI-My 2 cells after 3 days by WST1 assay2009Journal of medicinal chemistry, Mar-26, Volume: 52, Issue:6
Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.
AID1798071Enzyme Inhibition Assay from Article 10.1021/jm7010673: \\Structure-activity relationships of C6-uridine derivatives targeting plasmodia orotidine monophosphate decarboxylase.\\2008Journal of medicinal chemistry, Feb-14, Volume: 51, Issue:3
Structure-activity relationships of C6-uridine derivatives targeting plasmodia orotidine monophosphate decarboxylase.
AID1811Experimentally measured binding affinity data derived from PDB2002The Journal of biological chemistry, Aug-02, Volume: 277, Issue:31
Crystal structures of inhibitor complexes reveal an alternate binding mode in orotidine-5'-monophosphate decarboxylase.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2002The Journal of biological chemistry, Aug-02, Volume: 277, Issue:31
Crystal structures of inhibitor complexes reveal an alternate binding mode in orotidine-5'-monophosphate decarboxylase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (22.22)18.7374
1990's2 (22.22)18.2507
2000's5 (55.56)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]

Market Indicators

Research Demand Index: 12.21

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 Index12.21 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.21)

All Compounds (24.57)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
azauridine
Azauridine: A triazine nucleoside used as an antineoplastic antimetabolite. It interferes with pyrimidine biosynthesis thereby preventing formation of cellular nucleic acids. As the triacetate, it is also effective as an antipsoriatic.		2.3920N-glycosyl-1,2,4-triazineantimetabolite;
antineoplastic agent;
drug metabolite
uridine monophosphate
Uridine Monophosphate: 5'-Uridylic acid. A uracil nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.. uridine 5'-monophosphate : A pyrimidine ribonucleoside 5'-monophosphate having uracil as the nucleobase.		3.3770pyrimidine ribonucleoside 5'-monophosphate;
uridine 5'-phosphate		Escherichia coli metabolite;
human metabolite;
mouse metabolite
5-fluorouridine
[no description available]		2.0510organofluorine compound;
uridines		mutagen
xanthosine 5'-triphosphate
xanthosine 5'-phosphate : xanthosine phosphate compounds having phosphate groups at position 5'.. 5'-xanthylic acid : A purine ribonucleoside 5'-monophosphate having xanthine as the nucleobase.		2.0110purine ribonucleoside 5'-monophosphate;
xanthosine 5'-phosphate		Escherichia coli metabolite;
metabolite;
mouse metabolite
5-fluorouridine 5'-phosphate
5-fluorouridine 5'-monophosphate : A pyrimidine ribonucleoside 5'-monophosphate having 5-fluorouracil as the pyrimidine component.		2.0510organofluorine compound;
pyrimidine ribonucleoside 5'-monophosphate		drug metabolite
orotidylic acid
orotidylic acid: structure. orotidine 5'-phosphate : A pyrimidine ribonucleoside 5'-monophosphate having 6-carboxyuracil as the nucleobase.		2.4220pyrimidine ribonucleoside 5'-monophosphateEscherichia coli metabolite;
human metabolite;
mouse metabolite
phosphoribofuranosylbarbituric acid
[no description available]		2.4320
1-(5'-phospho-beta-d-ribofuranosyl)barbituric acid
6-oxouridine 5'-phosphate : A pyrimidine ribonucleoside 5'-monophosphate that is the 6-oxo derivative of UMP.		2.3720pyrimidine ribonucleoside 5'-monophosphate
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.		1.9710ammonium salt;
inorganic sulfate salt		fertilizer
ConditionIndicatedRelationship StrengthStudiesTrials