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Compound Detail

CHEMBL3818875

GSK2256294
🧪 Phase II
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🧪 Phase II
CNc1nc(C)nc(N[C@H]2CCC[C@@H](C(=O)NCc3ccc(C#N)cc3C(F)(F)F)C2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3818875
Name GSK2256294
Phase Phase II
Structure Type MOL
InChI Key LQHDJQIMETZMPH-ZBFHGGJFSA-N

Known Names

GSK-2256294 GSK-2256294A Gsk2256294
1
Targets
11
Activities
2
Assay Types
0
PK Parameters
14
Publications
3
Known Names
1
Indications
1
Mechanisms

Molecular Properties

447.5
MW (Da)
3.40
ALogP
7
HBA
3
HBD
115.6
PSA (Ų)
0.62
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Extended Properties

Molecular Formula C21H24F3N7O
MW 447.47
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness -1.46

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Epoxide hydratase inhibitor INHIBITOR Bifunctional epoxide hydrolase 2 ✓ ✓

Indications

Pulmonary Disease, Chronic Obstructive

Activity Summary

IC50 10 meas. best 10.57
Ki 1 meas. best 7.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 10.57 9.218 0.0 10
Bifunctional epoxide hydrolase 2
CHEMBL2409
 Ki 7.62 7.62 24.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional epoxide hydrolase 2 IC50 = 0.027 nM 10.57 Inhibition of recombinant human sEH using MNPC as substrate by fluorescence-base... 29614224
Bifunctional epoxide hydrolase 2 IC50 = 0.027 nM 10.57 Inhibition of recombinant human soluble epoxide hydrolase 32039601
Bifunctional epoxide hydrolase 2 IC50 = 0.028 nM 10.55 Inhibition of human recombinant sEH using 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic a... 26914744
Bifunctional epoxide hydrolase 2 IC50 = 0.66 nM 9.18 Inhibition of recombinant human soluble epoxide hydrolase expressed in HEK293 ce... 32039601
Bifunctional epoxide hydrolase 2 IC50 = 0.66 nM 9.18 Inhibition of human sEH BacMam transduced HEK293 cells assessed as reduction in ... 35859883
Bifunctional epoxide hydrolase 2 IC50 = 0.7 nM 9.15 Inhibition of human sEH (1 to 555 residues) expressed in Escherichia coli BL21-(... 33044073
Bifunctional epoxide hydrolase 2 IC50 = 0.9 nM 9.05 Inhibition of C-terminal domain of human sEH-H assessed as reduction in fluoresc... 35859883
Bifunctional epoxide hydrolase 2 IC50 = 1.585 nM 8.8 Inhibition of soluble epoxide hydrolase (unknown origin) 32039601
Bifunctional epoxide hydrolase 2 IC50 = 6.83 nM 8.17 Inhibition of soluble epoxide hydrolase in human whole blood 32039601
Bifunctional epoxide hydrolase 2 Ki = 24.0 nM 7.62 Displacement of (1R,3S)-N-(4-methoxy-2-(trifluoromethyl)benzyl)-3-((7-nitrobenzo... 35859883
Bifunctional epoxide hydrolase 2 IC50 = 110.0 nM 6.96 Inhibition of recombinant human sHE assessed as product formation preincubated f... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
32039601 10.1021/acs.jmedchem.9b01782 Bifunctional epoxide hydrolase 2 4
35859883 10.1021/acsmedchemlett.2c00073 Bifunctional epoxide hydrolase 2 4
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.1039/C6MD00042H Peroxisome proliferator-activated receptor delta 1
- 10.1039/C6MD00042H Peroxisome proliferator-activated receptor gamma 1
- 10.1039/C6MD00042H Peroxisome proliferator-activated receptor alpha 1
- 10.1039/C6MD00042H Bifunctional epoxide hydrolase 2 1
29614224 10.1021/acs.jmedchem.7b01804 Bifunctional epoxide hydrolase 2 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
26914744 10.1021/acs.jmedchem.5b01874 Bifunctional epoxide hydrolase 2 1
33044073 10.1021/acs.jmedchem.0c00561 Bifunctional epoxide hydrolase 2 1
33044073 10.1021/acs.jmedchem.0c00561 Polyunsaturated fatty acid 5-lipoxygenase 1

Data from ChEMBL 36 via Core Engine