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Compound Detail

CHEMBL186113

GW-328267
Phase I
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Phase I
CCn1nnc([C@H]2O[C@@H](n3cnc4c(N)nc(N[C@H](CO)Cc5ccccc5)nc43)[C@H](O)[C@@H]2O)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL186113
Name GW-328267
Phase Phase I
Structure Type MOL
InChI Key FLBKPDIBGNWXMT-NIQZGXKPSA-N

Known Names

Gw-328267 GW328267 GW328267X J2.047.755E
7
Targets
31
Activities
4
Assay Types
0
PK Parameters
20
Publications
4
Known Names
1
Indications

Molecular Properties

482.5
MW (Da)
-0.58
ALogP
14
HBA
5
HBD
195.2
PSA (Ų)
0.21
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Extended Properties

Molecular Formula C21H26N10O4
MW 482.51
Aromatic Rings 4
Heavy Atoms 35
NP-Likeness -0.17

Indications

Acute Lung Injury

Activity Summary

EC50 15 meas. best 9.0
Ki 11 meas. best 8.64
IC50 4 meas. best 9.4
Kd 1 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A2a
CHEMBL251
 IC50 9.4 9.4 0.4 1
Adenosine receptor A2a
CHEMBL251
 EC50 9.0 8.37 1.0 3
PBMC
CHEMBL613107
 IC50 8.89 8.715 1.3 2
Adenosine receptor A2a
CHEMBL251
 Ki 8.64 7.78 2.3 4
Adenosine receptor A3
CHEMBL256
 EC50 8.38 8.38 4.2 1
Adenosine receptor A3
CHEMBL256
 IC50 8.3 8.3 5.0 1
Adenosine receptor A3
CHEMBL256
 Kd 8.3 8.3 5.0 1
Adenosine receptor A2a
CHEMBL302
 EC50 8.0 8.0 10.0 2
Adenosine receptor A3
CHEMBL256
 Ki 7.8 7.2933 16.0 3
Adenosine receptor A2b
CHEMBL255
 EC50 7.29 6.3 51.0 4
Adenosine receptor A1
CHEMBL226
 Ki 6.43 6.2867 369.0 3
Adenosine receptor A1
CHEMBL226
 EC50 6.05 6.05 882.0 1
Adenosine receptor A2b
CHEMBL255
 Ki 5.89 5.89 1300.0 1
Cavia porcellus
CHEMBL369
 EC50 4.34 4.22 46000.0 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A2a IC50 = 0.4 nM 9.4 Agonist activity at adenosine A2A receptor in human neutrophils assessed as inhi... 20031406
Adenosine receptor A2a EC50 = 1.0 nM 9.0 Agonist activity at human recombinant adenosine A2A receptor expressed in CHO ce... 22468757
PBMC IC50 = 1.3 nM 8.89 Antiinflammatory activity in human PBMC assessed as inhibition of LPS-induced TN... 20031406
Adenosine receptor A2a Ki = 2.3 nM 8.64 Displacement of [3H]NECA from human recombinant adenosine A2A receptor expressed... 20031406
PBMC IC50 = 2.9 nM 8.54 Antiinflammatory activity in rat PBMC assessed as inhibition of LPS-induced TNFa... 20031406
Adenosine receptor A3 EC50 = 4.2 nM 8.38 Agonist activity at human adenosine A3 receptor expressed in CHO cells by GTPPga... 20031406
Adenosine receptor A3 IC50 = 5.0 nM 8.3 Antagonist activity at human adenosine A3 receptor expressed in CHO cells assess... 22468757
Adenosine receptor A3 Kd = 5.012 nM 8.3 Antagonist activity at human adenosine A3 receptor expressed in CHO cells assess... 22468757
Adenosine receptor A2a EC50 = 8.8 nM 8.06 Potency against cAMP formation in CHO cells expressing recombinant human A2A rec... 15267242
Adenosine receptor A2a EC50 = 9.0 nM 8.05 Agonist activity at adenosine receptor A2a (unknown origin) assessed as cAMP for... 24164628
Adenosine receptor A2a EC50 = 10.0 nM 8.0 Agonist activity at adenosine receptor A2a in isolated rat aorta assessed as eff... 24164628
Adenosine receptor A2a EC50 = 10.0 nM 8.0 Efficacy against phenylephrine precontracted tissue relaxation in rat aorta 15267242
Adenosine receptor A2a Ki = 16.0 nM 7.8 Displacement of [3H]CGS21680 from human recombinant adenosine A2A receptor expre... 22468757
Adenosine receptor A3 Ki = 16.0 nM 7.8 Displacement of [125I]I-AB-MECA from human recombinant adenosine A3 receptor exp... 22468757
Adenosine receptor A2a Ki = 46.0 nM 7.34 Binding affinity to human recombinant adenosine receptor A2a 24164628
Adenosine receptor A2a Ki = 46.0 nM 7.34 Inhibition of [3H]ZM-241385 binding to human adenosine A2A receptor expressed in... 15267242
Adenosine receptor A2b EC50 = 51.0 nM 7.29 Agonist activity at human adenosine A2B receptor expressed in CHO cells assessed... 20031406
Adenosine receptor A3 Ki = 92.0 nM 7.04 Binding affinity to human recombinant adenosine A3 receptor 24164628
Adenosine receptor A3 Ki = 92.0 nM 7.04 Inhibition of [3H]NECA binding to human adenosine A3 receptor expressed in HeLa ... 15267242
Adenosine receptor A1 Ki = 369.0 nM 6.43 Binding affinity to human recombinant adenosine A1 receptor 24164628

Literature References

PubMed DOI Target Context # Activities
15267242 10.1021/jm031143+ Cavia porcellus 12
15267242 10.1021/jm031143+ Adenosine receptor A2a 6
24164628 10.1021/jm4011669 Adenosine receptor A2a 5
15267242 10.1021/jm031143+ Adenosine receptor A2b 4
22468757 10.1021/jm300087j Adenosine receptor A3 4
24164628 10.1021/jm4011669 Unchecked 3
22468757 10.1021/jm300087j Adenosine receptor A2a 3
20031406 10.1016/j.bmcl.2009.11.131 Adenosine receptor A2a 2
20031406 10.1016/j.bmcl.2009.11.131 Adenosine receptor A3 2
20031406 10.1016/j.bmcl.2009.11.131 PBMC 2
20031406 10.1016/j.bmcl.2009.11.131 Adenosine receptor A2b 1
24164628 10.1021/jm4011669 Adenosine receptor A2b 1
22468757 10.1021/jm300087j Unchecked 1
22468757 10.1021/jm300087j Adenosine receptors; A1 & A3 1
22468757 10.1021/jm300087j Adenosine receptor A1 1
20031406 10.1016/j.bmcl.2009.11.131 Adenosine receptor A1 1
15267242 10.1021/jm031143+ Adenosine receptors; A2a & A3 1
15267242 10.1021/jm031143+ Adenosine A2 receptor 1
15267242 10.1021/jm031143+ Adenosine receptors; A1 & A2a 1
15267242 10.1021/jm031143+ Adenosine receptor A3 1

Data from ChEMBL 36 via Core Engine