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Compound Detail

CHEMBL269864

ULODESINE
🧪 Phase II
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🧪 Phase II
O=c1[nH]cnc2c(CN3C[C@H](CO)[C@@H](O)C3)c[nH]c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL269864
Name ULODESINE
Phase Phase II
Structure Type MOL
InChI Key AFNHHLILYQEHKK-BDAKNGLRSA-N

Known Names

BCX-3408 Bcx-4208 BCX4208 Dadme-immucillin h LR-09 R-3421 Ulodesina Ulodesine
4
Targets
19
Activities
1
Assay Types
0
PK Parameters
10
Publications
8
Known Names
3
Indications
1
Mechanisms

Molecular Properties

264.3
MW (Da)
-0.96
ALogP
5
HBA
4
HBD
105.2
PSA (Ų)
0.57
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Year 2012

Extended Properties

Molecular Formula C12H16N4O3
MW 264.29
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.02

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Purine nucleoside phosphorylase inhibitor INHIBITOR Purine nucleoside phosphorylase ✓ ✓

Indications

Gout Hyperuricemia Osteoarthritis

Activity Summary

Ki 19 meas. best 10.97

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Purine nucleoside phosphorylase
CHEMBL4338
 Ki 10.97 9.9725 0.0 12
Purine nucleoside phosphorylase
CHEMBL2935
 Ki 10.0 10.0 0.1 1
Purine nucleoside phosphorylase
CHEMBL4523389
 Ki 9.3 9.3 0.5 2
Purine nucleoside phosphorylase
CHEMBL5648
 Ki 9.3 9.3 0.5 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Purine nucleoside phosphorylase Ki = 0.0107 nM 10.97 Equilibrium binding affinity to wild type human PNP 18778937
Purine nucleoside phosphorylase Ki = 0.0107 nM 10.97 Inhibition of human PNP 18251493
Purine nucleoside phosphorylase Ki = 0.011 nM 10.96 Inhibition of human purine nucleoside phosphorylase by xanthine-oxidase coupled ... 18800772
Purine nucleoside phosphorylase Ki = 0.016 nM 10.8 Dissociation constant against Human Purine Nucleoside Phosphorylase was reported 14613329
Purine nucleoside phosphorylase Ki = 0.016 nM 10.8 Inhibition of human His-tagged PNP assessed as equilibrium dissociation constant... 30964283
Purine nucleoside phosphorylase Ki = 0.016 nM 10.8 Binding affinity to human PNP assessed as inhibition constant by TR-FRET assay 38701712
Purine nucleoside phosphorylase Ki = 0.1 nM 10.0 Inhibition of bovine PNP 18251493
Purine nucleoside phosphorylase Ki = 0.27 nM 9.57 Equilibrium binding affinity to human PNP His257Gly mutant 18778937
Purine nucleoside phosphorylase Ki = 0.5 nM 9.3 Inhibition of Plasmodium falciparum PNP 18251493
Purine nucleoside phosphorylase Ki = 0.5 nM 9.3 Binding affinity to Plasmodium falciparum 3D7 PNP assessed as inhibition constan... 38701712
Purine nucleoside phosphorylase Ki = 0.5 nM 9.3 Inhibition of Plasmodium falciparum His-tagged PNP expressed in Escherichia coli... 30964283
Purine nucleoside phosphorylase Ki = 0.5 nM 9.3 Inhibition of Plasmodium falciparum purine nucleoside phosphorylase assessed as ... 18800772
Purine nucleoside phosphorylase Ki = 1.1 nM 8.96 Binding affinity towards Human Purine Nucleoside Phosphorylase was reported 14613329
Purine nucleoside phosphorylase Ki = 1.1 nM 8.96 Inhibition of human purine nucleoside phosphorylase assessed as slow onset inhib... 18800772
Purine nucleoside phosphorylase Ki = 1.1 nM 8.96 Initial binding affinity to wild type human PNP 18778937
Purine nucleoside phosphorylase Ki = 1.1 nM 8.96 Inhibition of human His-tagged PNP assessed as inhibitor constant for enzyme-inh... 30964283
Purine nucleoside phosphorylase Ki = 1.1 nM 8.96 Inhibition of human PNP 30769179

Literature References

PubMed DOI Target Context # Activities
18778937 10.1016/j.bmcl.2008.08.047 Purine nucleoside phosphorylase 5
18251493 10.1021/jm701265n Purine nucleoside phosphorylase 3
18800772 10.1021/jm800792b Purine nucleoside phosphorylase 3
30964283 10.1021/acs.jmedchem.9b00182 Purine nucleoside phosphorylase 3
14613329 10.1021/jm030305z Purine nucleoside phosphorylase 2
38701712 10.1016/j.ejmech.2024.116437 Purine nucleoside phosphorylase 2
19170524 10.1021/jm801421q Purine nucleoside phosphorylase 1
18778937 10.1016/j.bmcl.2008.08.047 Unchecked 1
30627387 10.1039/C8MD00372F Purine nucleoside phosphorylase 1
30769179 10.1016/j.ejmech.2019.01.043 Purine nucleoside phosphorylase 1

Data from ChEMBL 36 via Core Engine