Page last updated: 2024-10-15

ulodesine

Description

ulodesine: a purine nucleoside phosphorylase inhibitor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135449518
CHEMBL ID269864
SCHEMBL ID16320802
SCHEMBL ID474735
MeSH IDM000600402

Synonyms (38)

Synonym
7-[[(3r,4r)-3-(hydroxymethyl)-4-oxidanyl-pyrrolidin-1-ium-1-yl]methyl]-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
7-{[(3r,4r)-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl]methyl}-1,5-dihydro-4h-pyrrolo[3,2-d]pyrimidin-4-one
bdbm22109
dadme-immh,7
chembl269864 ,
7-{[(3r,4r)-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl]methyl}-1h,4h,5h-pyrrolo[3,2-d]pyrimidin-4-one
1N3I
7-[[(3r,4r)-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl]methyl]-1,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
bcx4208
bcx-3408
ulodesine
r-3421
dadme-immucillin h
bcx-4208
ulodesine [usan:inn]
unii-jng8l9460y
jng8l9460y ,
548486-59-5
ulodesine (usan)
D10431
ulodesine [who-dd]
ulodesine [usan]
7-(((3r,4r)-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl)methyl(-1,5-dihydro-4h-pyrrolo(3,2-d)pyrimidin-4-one
7-(((3r,4r)-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl)methyl)-3,5-dihydro-4h-pyrrolo(3,2-d)pyrimidin-4-one
ulodesine [inn]
4h-pyrrolo(3,2-d)pyrimidin-4-one, 1,5-dihydro-7-(((3r,4r)-3-hydroxy-4-(hydroxymethyl)-1-pyrrolidinyl)methyl)-
SCHEMBL16320802
SCHEMBL474735
DTXSID00203332
7-{[(3r,4r)-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl]methyl}-3h,5h-pyrrolo[3,2-d]pyrimidin-4-one
DB12353
7-(((3r,4r)-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl)methyl)-1h-pyrrolo[3,2-d]pyrimidin-4(5h)-one
Q27281592
F82076
MS-23730
HY-19480
CS-0015580
7-[[(3r,4r)-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl]methyl]-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Purine Nucleoside PhosphorylaseMycobacterium tuberculosisKi0.00130.00130.00130.0013AID977610
Chain B, Purine Nucleoside PhosphorylaseMycobacterium tuberculosisKi0.00130.00130.00130.0013AID977610
Purine nucleoside phosphorylaseHomo sapiens (human)Ki0.00050.00000.52897.0000AID1571179; AID1578788; AID1578789; AID1649931; AID1798156; AID317479; AID371442; AID386682; AID386683; AID409913; AID409914; AID409918
Purine nucleoside phosphorylase Bos taurus (cattle)Ki0.00070.00000.53072.7000AID1798156; AID317480
Purine nucleoside phosphorylasePlasmodium falciparum 3D7Ki0.00050.00050.00050.0005AID1578790
Purine nucleoside phosphorylasePlasmodium falciparum (malaria parasite P. falciparum)Ki0.00050.00050.00540.0290AID317481; AID386684
Histamine H3 receptorCavia porcellus (domestic guinea pig)Ki0.00050.00010.00300.0126AID386684
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
inosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
urate biosynthetic processPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of T cell proliferationPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of alpha-beta T cell differentiationPurine nucleoside phosphorylaseHomo sapiens (human)
allantoin metabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
nucleobase-containing compound metabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
inosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
deoxyinosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
deoxyadenosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
purine ribonucleoside salvagePurine nucleoside phosphorylaseHomo sapiens (human)
IMP catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
nicotinamide riboside catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
immune responsePurine nucleoside phosphorylaseHomo sapiens (human)
nucleotide biosynthetic processPurine nucleoside phosphorylaseHomo sapiens (human)
response to xenobiotic stimulusPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of interleukin-2 productionPurine nucleoside phosphorylaseHomo sapiens (human)
purine-containing compound salvagePurine nucleoside phosphorylaseHomo sapiens (human)
dAMP catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
purine ribonucleoside salvagePurine nucleoside phosphorylase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
nucleoside bindingPurine nucleoside phosphorylaseHomo sapiens (human)
purine nucleobase bindingPurine nucleoside phosphorylaseHomo sapiens (human)
purine-nucleoside phosphorylase activityPurine nucleoside phosphorylaseHomo sapiens (human)
protein bindingPurine nucleoside phosphorylaseHomo sapiens (human)
phosphate ion bindingPurine nucleoside phosphorylaseHomo sapiens (human)
identical protein bindingPurine nucleoside phosphorylaseHomo sapiens (human)
guanosine phosphorylase activityPurine nucleoside phosphorylaseHomo sapiens (human)
purine-nucleoside phosphorylase activityPurine nucleoside phosphorylase Bos taurus (cattle)
guanosine phosphorylase activityPurine nucleoside phosphorylase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
extracellular regionPurine nucleoside phosphorylaseHomo sapiens (human)
cytoplasmPurine nucleoside phosphorylaseHomo sapiens (human)
cytosolPurine nucleoside phosphorylaseHomo sapiens (human)
secretory granule lumenPurine nucleoside phosphorylaseHomo sapiens (human)
extracellular exosomePurine nucleoside phosphorylaseHomo sapiens (human)
ficolin-1-rich granule lumenPurine nucleoside phosphorylaseHomo sapiens (human)
cytoplasmPurine nucleoside phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID1571179Inhibition of recombinant human PNP expressed in Escherichia coli BL21 (DE3) using inosine as substrate preincubated for 5.5 hrs followed by substrate addition by xanthine oxidase coupled assay2018MedChemComm, Dec-01, Volume: 9, Issue:12
The transition to magic bullets - transition state analogue drug design.
AID409921Ratio of relative binding Km/Ki for wild type human PNP to relative binding affinity Km/Ki for human PNP His257Gly mutant2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Immucillins in custom catalytic-site cavities.
AID317481Inhibition of Plasmodium falciparum PNP2008Journal of medicinal chemistry, Feb-28, Volume: 51, Issue:4
Azetidine based transition state analogue inhibitors of N-ribosyl hydrolases and phosphorylases.
AID371442Inhibition of human PNP by xanthine-oxidase coupled assay2009Journal of medicinal chemistry, Feb-26, Volume: 52, Issue:4
Third-generation immucillins: syntheses and bioactivities of acyclic immucillin inhibitors of human purine nucleoside phosphorylase.
AID1649931Inhibition of human PNP2019European journal of medicinal chemistry, Mar-15, Volume: 166Pharmacological urate-lowering approaches in chronic kidney disease.
AID1578790Inhibition of Plasmodium falciparum His-tagged PNP expressed in Escherichia coli assessed as inhibitor constant for enzyme-inhibitor complex formation by measuring reduction in uric acid formation by spectrophotometric method2019Journal of medicinal chemistry, 09-26, Volume: 62, Issue:18
Plasmodium Purine Metabolism and Its Inhibition by Nucleoside and Nucleotide Analogues.
AID386683Inhibition of human purine nucleoside phosphorylase by xanthine-oxidase coupled assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
A beta-fluoroamine inhibitor of purine nucleoside phosphorylase.
AID164742Dissociation constant against Human Purine Nucleoside Phosphorylase was reported2003Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24
Synthesis of second-generation transition state analogues of human purine nucleoside phosphorylase.
AID409914Equilibrium binding affinity to wild type human PNP2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Immucillins in custom catalytic-site cavities.
AID409918Equilibrium binding affinity to human PNP His257Gly mutant2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Immucillins in custom catalytic-site cavities.
AID1578789Inhibition of human His-tagged PNP assessed as equilibrium dissociation constant by measuring reduction in uric acid formation by spectrophotometric method2019Journal of medicinal chemistry, 09-26, Volume: 62, Issue:18
Plasmodium Purine Metabolism and Its Inhibition by Nucleoside and Nucleotide Analogues.
AID409920Ratio of Km for human PNP His257Gly mutant to Ki for human PNP His257Gly mutant relative to inosine2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Immucillins in custom catalytic-site cavities.
AID386684Inhibition of Plasmodium falciparum purine nucleoside phosphorylase assessed as slow onset inhibition constant by xanthine-oxidase coupled assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
A beta-fluoroamine inhibitor of purine nucleoside phosphorylase.
AID317479Inhibition of human PNP2008Journal of medicinal chemistry, Feb-28, Volume: 51, Issue:4
Azetidine based transition state analogue inhibitors of N-ribosyl hydrolases and phosphorylases.
AID164741Binding affinity towards Human Purine Nucleoside Phosphorylase was reported2003Journal of medicinal chemistry, Nov-20, Volume: 46, Issue:24
Synthesis of second-generation transition state analogues of human purine nucleoside phosphorylase.
AID1578788Inhibition of human His-tagged PNP assessed as inhibitor constant for enzyme-inhibitor complex formation by measuring reduction in uric acid formation by spectrophotometric method2019Journal of medicinal chemistry, 09-26, Volume: 62, Issue:18
Plasmodium Purine Metabolism and Its Inhibition by Nucleoside and Nucleotide Analogues.
AID317480Inhibition of bovine PNP2008Journal of medicinal chemistry, Feb-28, Volume: 51, Issue:4
Azetidine based transition state analogue inhibitors of N-ribosyl hydrolases and phosphorylases.
AID409916Ratio of Km for wild type human PNP to Ki for wild type human PNP relative to inosine2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Immucillins in custom catalytic-site cavities.
AID386682Inhibition of human purine nucleoside phosphorylase assessed as slow onset inhibition constant by xanthine-oxidase coupled assay2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
A beta-fluoroamine inhibitor of purine nucleoside phosphorylase.
AID409913Initial binding affinity to wild type human PNP2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
Immucillins in custom catalytic-site cavities.
AID1798156PNP Inhibition Assay from Article 10.1021/jm701265n: \\Azetidine based transition state analogue inhibitors of N-ribosyl hydrolases and phosphorylases.\\2008Journal of medicinal chemistry, Feb-28, Volume: 51, Issue:4
Azetidine based transition state analogue inhibitors of N-ribosyl hydrolases and phosphorylases.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2003Biochemistry, May-27, Volume: 42, Issue:20
Over-the-barrier transition state analogues and crystal structure with Mycobacterium tuberculosis purine nucleoside phosphorylase.
AID1811Experimentally measured binding affinity data derived from PDB2003Biochemistry, May-27, Volume: 42, Issue:20
Over-the-barrier transition state analogues and crystal structure with Mycobacterium tuberculosis purine nucleoside phosphorylase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's11 (55.00)29.6817
2010's8 (40.00)24.3611
2020's1 (5.00)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%
Reviews6 (30.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (70.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]