GSK2256294

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Synonyms
Status
Molecule Category UNKNOWN
UNII L33EX3XR0T

Structure

InChI Key LQHDJQIMETZMPH-ZBFHGGJFSA-N
Smiles CNc1nc(C)nc(N[C@H]2CCC[C@@H](C(=O)NCc3ccc(C#N)cc3C(F)(F)F)C2)n1
InChI
InChI=1S/C21H24F3N7O/c1-12-28-19(26-2)31-20(29-12)30-16-5-3-4-14(9-16)18(32)27-11-15-7-6-13(10-25)8-17(15)21(22,23)24/h6-8,14,16H,3-5,9,11H2,1-2H3,(H,27,32)(H2,26,28,29,30,31)/t14-,16+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H24F3N7O
Molecular Weight 447.47
AlogP 3.4
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 6.0
Polar Surface Area 115.62
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 32.0

Bioactivity

Mechanism of Action Action Reference
Epoxide hydratase inhibitor INHIBITOR PubMed PubMed
Protein: Epoxide hydratase
Description: Bifunctional epoxide hydrolase 2
Organism : Homo sapiens
P34913 ENSG00000120915
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Serine protease Serine protease SC clan Serine protease S33 family
- 0-110 - - -
Assay Description Organism Bioactivity Reference
Inhibition of recombinant human sHE assessed as product formation preincubated for 30 mins followed by addition of (3-phenyl-cyano-(6-methoxy-2-naphthalenyl)methyl ester-2-oxirane-acetic acid as substrate measured after 30 mins by fluorescence analysis Homo sapiens 110.0 nM
Inhibition of recombinant human sEH using MNPC as substrate by fluorescence-based assay Homo sapiens 0.027 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 0.41 %
Inhibition of human recombinant sEH using 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid as substrate assessed as formation of 14,15-dihydroxy-5Z,8Z,11Zeicosatrienoic acid preincubated for 2 hrs followed by substrate addition measured after 1 hr by LC/MS method Homo sapiens 0.028 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 17.83 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 17.7 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.01 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.16 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.01 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.16 %
Inhibition of soluble epoxide hydrolase (unknown origin) Homo sapiens 1.585 nM
Inhibition of recombinant human soluble epoxide hydrolase Homo sapiens 0.027 nM
Inhibition of recombinant human soluble epoxide hydrolase expressed in HEK293 cells Homo sapiens 0.66 nM
Inhibition of soluble epoxide hydrolase in human whole blood Homo sapiens 6.83 nM
Inhibition of human sEH (1 to 555 residues) expressed in Escherichia coli BL21-(DE3) using PHOME substrate incubated for 30 to 45 mins by fluorescence based assay Homo sapiens 0.7 nM

Cross References

Resources Reference
ChEMBL CHEMBL3818875
FDA SRS L33EX3XR0T
Guide to Pharmacology 9718
SureChEMBL SCHEMBL2677671
ZINC ZINC000167915141
CONTENTS