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Compound Detail

CHEMBL490461

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CCOC(=O)c1c(Cc2cccc(Cl)c2)[nH]c2c1cc(O)c1ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL490461
Phase Preclinical
Structure Type MOL
InChI Key UNDGVXYIMIZWAS-UHFFFAOYSA-N
2
Targets
9
Activities
1
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

379.8
MW (Da)
5.45
ALogP
3
HBA
2
HBD
62.3
PSA (Ų)
0.46
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H18ClNO3
MW 379.84
Aromatic Rings 4
Heavy Atoms 27
NP-Likeness -0.17

Activity Summary

IC50 9 meas. best 7.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 7.07 6.245 86.0 6
Prostaglandin E synthase
CHEMBL5658
 IC50 6.22 6.0467 600.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 86.0 nM 7.07 Inhibition of human recombinant 5-lipoxygenase expressed in Escherichia coli ass... 19492852
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 230.0 nM 6.64 Inhibition of 5-lipoxygenase in A-23817-challenged human neutrophils assessed as... 19492852
Prostaglandin E synthase IC50 = 600.0 nM 6.22 Inhibition of mPGES1 in IL1-beta induced human A549 cell microsomal membrane ass... 19884011
Prostaglandin E synthase IC50 = 600.0 nM 6.22 Inhibition of mPGES-1 in IL-1beta-stimulated human A549 cell microsomal membrane... 26088337
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 830.0 nM 6.08 Inhibition of 5-lipoxygenase activity in LPS/fMLP-stimulated human whole blood c... 19492852
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 830.0 nM 6.08 Inhibition of 5-lipoxygenase activity in LPS/fMLP-stimulated human whole blood c... 19492852
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 1600.0 nM 5.8 Inhibition of 5-lipoxygenase in A-23817-challenged human whole blood assessed as... 19492852
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 1600.0 nM 5.8 Inhibition of 5-lipoxygenase in A-23817-challenged human whole blood assessed as... 19492852
Prostaglandin E synthase IC50 = 2000.0 nM 5.7 Inhibition of mPGES1 in IL1-beta induced human A549 cells assessed as PGE2 produ... 19884011

Literature References

PubMed DOI Target Context # Activities
19884011 10.1016/j.bmc.2009.10.025 Prostaglandin E synthase 14
19492852 10.1021/jm900212y Polyunsaturated fatty acid 5-lipoxygenase 9
19884011 10.1016/j.bmc.2009.10.025 Rattus norvegicus 8
19492852 10.1021/jm900212y Rattus norvegicus 3
19884011 10.1016/j.bmc.2009.10.025 Mus musculus 3
19884011 10.1016/j.bmc.2009.10.025 Prostaglandin G/H synthase 1 2
19884011 10.1016/j.bmc.2009.10.025 Prostaglandin G/H synthase 2 2
19492852 10.1021/jm900212y Neutrophil 1
19884011 10.1016/j.bmc.2009.10.025 A549 1
26088337 10.1016/j.bmc.2015.05.045 Prostaglandin E synthase 1

Data from ChEMBL 36 via Core Engine