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Compound Detail

CHEMBL431733

NAMODENOSON
🧪 Phase III
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🧪 Phase III
CNC(=O)[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)nc(Cl)nc32)[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL431733
Name NAMODENOSON
Phase Phase III
Structure Type MOL
InChI Key IPSYPUKKXMNCNQ-PFHKOEEOSA-N

Known Names

CF-102 Cf102 Chloro-ib-meca CI-IB-MECA CL-IB-MECA Namodenoson
18
Targets
139
Activities
3
Assay Types
0
PK Parameters
20
Publications
6
Known Names
4
Indications
1
Mechanisms

Molecular Properties

544.7
MW (Da)
1.06
ALogP
9
HBA
4
HBD
134.4
PSA (Ų)
0.28
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -denoson
USAN Year 2016

Extended Properties

Molecular Formula C18H18ClIN6O4
MW 544.74
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -0.35

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Adenosine A3 receptor agonist AGONIST Adenosine receptor A3 ✓ ✓

Indications

Carcinoma, Hepatocellular Non-alcoholic Fatty Liver Disease Non-alcoholic Fatty Liver Disease Hepatitis C, Chronic

Activity Summary

Ki 119 meas. best 9.74
EC50 11 meas. best 9.82
IC50 9 meas. best 8.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A3
CHEMBL1075269
 EC50 9.82 9.58 0.1 2
Adenosine receptor A3
CHEMBL1075269
 Ki 9.74 9.74 0.2 1
Adenosine receptor A3
CHEMBL256
 Ki 9.7 8.8671 0.2 41
Adenosine receptor A3
CHEMBL3360
 Ki 9.48 9.3622 0.3 9
Peroxisome proliferator-activated receptor delta
CHEMBL3979
 Ki 9.37 9.37 0.4 1
Adenosine receptor A3
CHEMBL256
 EC50 8.92 8.695 1.2 4
Adenosine receptor A3
CHEMBL256
 IC50 8.92 8.79 1.2 2
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 Ki 8.66 8.66 2.2 1
Adenosine receptor A1
CHEMBL226
 Ki 8.28 6.5064 5.3 22
Adenosine receptor A1
CHEMBL3688
 Ki 7.46 7.46 35.0 1
Adenosine receptor A1
CHEMBL318
 Ki 7.27 6.2867 54.0 6
Adenosine receptor A2a
CHEMBL302
 Ki 7.25 6.4833 56.0 6
Peroxisome proliferator-activated receptor delta
CHEMBL3979
 EC50 6.72 5.625 191.0 2
Adenosine receptor A2a
CHEMBL251
 Ki 6.4 5.5696 401.0 23
Adenosine receptor A1
CHEMBL4975
 Ki 6.05 6.05 890.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 EC50 5.85 5.85 1420.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 5.56 5.56 2770.0 2
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 EC50 5.53 5.53 2940.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.2 5.0143 6309.6 7
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 5.0 5.0 10000.0 2
Adenosine receptor A2a
CHEMBL2115
 Ki 5.0 5.0 10000.0 1
Equilibrative nucleoside transporter 1
CHEMBL4604
 Ki 4.82 4.82 15200.0 1
Unchecked
CHEMBL612545
 EC50 4.39 4.39 40600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A3 EC50 = 0.15 nM 9.82 Agonist activity at mouse adenosine A3 receptor expressed in HEK293 cell membran... 23789857
Adenosine receptor A3 Ki = 0.18 nM 9.74 Displacement of [125I]N6-(-amino-3-iodobenzyl)adenosine-5'-N-methyl-uronamide fr... 18424135
Adenosine receptor A3 Ki = 0.2 nM 9.7 Displacement of [3H]NECA from recombinant human adenosine A3 receptor expressed ... 30108902
Adenosine receptor A3 Ki = 0.22 nM 9.66 Displacement of [125I]AB-MECA from adenosine A3 receptors in bovine cortical mem... 15743197
Adenosine receptor A3 Ki = 0.22 nM 9.66 Displacement of [3H]AB-MECA from human adenosine A3 receptor expressed in CHO ce... 17927167
Adenosine receptor A3 Ki = 0.22 nM 9.66 Displacement of [125I]AB-MECA from human adenosine A3 receptor expressed in CHO ... 18269230
Adenosine receptor A3 Ki = 0.22 nM 9.66 Displacement of [125I]AB-MECA from human A3 adenosine receptor expressed in CHO ... 22257095
Adenosine receptor A3 Ki = 0.22 nM 9.66 Displacement of [125I]AB-MECA from human adenosine A3 receptor expressed in CHO ... 24077183
Adenosine receptor A3 Ki = 0.33 nM 9.48 Tested for the binding affinity of A3 receptor by displacing N6-[[125I]-4-amino-... 7932588
Adenosine receptor A3 Ki = 0.33 nM 9.48 Displacement of [125I]AB-MECA from adenosine A3 receptor from HEK293 cell membra... 9703464
Adenosine receptor A3 Ki = 0.33 nM 9.48 Binding affinity for rat Adenosine A3 receptor in CHO cells [125I]-iodo-AB-MECA 12930138
Adenosine receptor A3 Ki = 0.33 nM 9.48 Binding affinity for rat Adenosine A3 receptor 12617898
Adenosine receptor A3 Ki = 0.33 nM 9.48 Displacement of [125I]I-AB-MECA from human rat adenosine A3 receptor expressed i... 22468757
Adenosine receptor A3 Ki = 0.33 nM 9.48 Displacement of [125I]I-AB-MECA from rat adenosine A3 receptor expressed in CHO ... 18811138
Adenosine receptor A3 Ki = 0.33 nM 9.48 Displacement of radioligand from rat A3 adenosine receptor 18424135
Adenosine receptor A3 Ki = 0.33 nM 9.48 Displacement of [125I]AB-MECA binding to Adenosine A3 receptor expressed in CHO ... 15481989
Adenosine receptor A3 Ki = 0.33 nM 9.48 Inhibition of [125I]AB-MECA binding to rat Adenosine A3 receptor expressed in CH... 15771421
Adenosine receptor A3 Ki = 0.3802 nM 9.42 Displacement of [125I]I-AB-MEAC from human adenosine A3 receptor expressed in CH... 18973967
Peroxisome proliferator-activated receptor delta Ki = 0.43 nM 9.37 Displacement of Fluormone-Pan-PPAR Green from human GST-tagged PPARdelta LBD by ... 28799755
Adenosine receptor A3 EC50 = 0.46 nM 9.34 Agonist activity at mouse adenosine A3 receptor expressed in HEK293 cell membran... 26890707

Literature References

PubMed DOI Target Context # Activities
12238926 10.1021/jm020211+ Adenosine receptor A3 10
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
19879151 10.1016/j.bmc.2009.10.011 Adenosine receptor A3 3
15771421 10.1021/jm049580r Adenosine receptor A3 3
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptor A2a 3
35152062 10.1016/j.ejmech.2022.114103 Broad substrate specificity ATP-binding cassette transporter ABCG2 3
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptor A3 3
28799755 10.1021/acs.jmedchem.7b00805 Peroxisome proliferator-activated receptor gamma 3
24931275 10.1016/j.bmc.2014.05.036 Adenosine receptor A3 3
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptor A1 3
31806266 10.1016/j.bmc.2019.115226 Peroxisome proliferator-activated receptor delta 3
25422861 10.1021/jm501021n Mus musculus 3
31806266 10.1016/j.bmc.2019.115226 Peroxisome proliferator-activated receptor gamma 3
18255292 10.1016/j.bmcl.2008.01.070 Adenosine receptor A3 2
22468757 10.1021/jm300087j Adenosine receptor A3 2
18752961 10.1016/j.bmc.2008.08.007 Adenosine receptor A3 2
18811138 10.1021/jm8008647 Adenosine receptor A3 2
12930138 10.1021/jm034098e Adenosine receptor A3 2
22468757 10.1021/jm300087j Unchecked 2

Data from ChEMBL 36 via Core Engine