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Compound Detail

CHEMBL182032

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Cc1c(CC(C)(C)C(=O)O)n(Cc2ccc(Cl)cc2)c2ccc(-c3ccc(-c4ccccc4)c(F)c3)cc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL182032
Phase Preclinical
Structure Type MOL
InChI Key WNFJTGITKNIPNM-UHFFFAOYSA-N
5
Targets
15
Activities
1
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

526.0
MW (Da)
8.78
ALogP
2
HBA
1
HBD
42.2
PSA (Ų)
0.23
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C33H29ClFNO2
MW 526.05
Aromatic Rings 5
Heavy Atoms 38
NP-Likeness -0.60

Activity Summary

IC50 15 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin E synthase
CHEMBL5658
 IC50 8.52 7.95 3.0 4
Unchecked
CHEMBL612545
 IC50 8.52 7.6267 3.0 3
Prostaglandin E synthase 2
CHEMBL4411
 IC50 8.15 8.15 7.0 1
A549
CHEMBL392
 IC50 6.31 5.7217 490.0 6
Thromboxane-A synthase
CHEMBL1835
 IC50 5.85 5.85 1400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 3.0 nM 8.52 Inhibition of mPGES1 18459759
Prostaglandin E synthase IC50 = 3.0 nM 8.52 Inhibition of human recombinant mPGES-1 using PGH2 as substrate incubated 20 min... 23266122
Prostaglandin E synthase 2 IC50 = 7.0 nM 8.15 Inhibitory concentration against human prostaglandin E2 synthase (mPGES-1) 15953724
Unchecked IC50 = 7.0 nM 8.15 Inhibition of mPGES1 expressed in human HeLa cells assessed as inhibition of IL-... 20025212
Prostaglandin E synthase IC50 = 7.0 nM 8.15 Inhibition of human microsomal PGES1 in cell-free system assessed as inhibition ... 21466167
Prostaglandin E synthase IC50 = 12.0 nM 7.92 Inhibition of mPGES1 in IL1-beta treated human A549 cell microsomal membrane ass... 19719242
Prostaglandin E synthase IC50 = 62.0 nM 7.21 Inhibition of human mPGES1 assessed as PGE2 level after 41 sec by ELISA 20144869
A549 IC50 = 490.0 nM 6.31 In vitro Inhibition against PGE-2 using IL-1-beta-stimulated A549 epithelial lun... 15953724
A549 IC50 = 500.0 nM 6.3 Inhibition of PGE2 synthesis in human A549 cells 18459759
Unchecked IC50 = 610.0 nM 6.21 In vitro Inhibition against PGE-2 using IL-1-beta-stimulated human synoviocyte c... 15953724
Thromboxane-A synthase IC50 = 1400.0 nM 5.85 In vitro inhibition against human Thromboxane synthase 15953724
A549 IC50 = 2000.0 nM 5.7 In vitro Inhibition against PGF2-alpha using IL-1-beta-stimulated A549 epithelia... 15953724
A549 IC50 = 2000.0 nM 5.7 Inhibition of PGE2alpha synthesis in human A549 cells 18459759
A549 IC50 = 6000.0 nM 5.22 Inhibition of IL1-beta stimulated PGE2 production in human A549 cells 18459759
A549 IC50 = 8000.0 nM 5.1 In vitro Inhibition against PGE-2 using IL-1-beta-stimulated A549 epithelial lun... 15953724

Literature References

PubMed DOI Target Context # Activities
15953724 10.1016/j.bmcl.2005.05.027 A549 3
18459759 10.1021/jm800197b A549 3
15953724 10.1016/j.bmcl.2005.05.027 Prostaglandin E synthase 2 2
19719242 10.1021/jm900481c Prostaglandin E synthase 2
18459759 10.1021/jm800197b Thromboxane-A synthase 1
23266122 10.1016/j.bmcl.2012.10.040 Prostaglandin E synthase 1
23266122 10.1016/j.bmcl.2012.10.040 Unchecked 1
21466167 10.1021/jm101309g Prostaglandin E synthase 1
20144869 10.1016/j.bmcl.2010.01.060 Prostaglandin E synthase 1
20025212 10.1021/jm9012505 Unchecked 1
19719242 10.1021/jm900481c Unchecked 1
19719242 10.1021/jm900481c Prostaglandin G/H synthase 2 1
19719242 10.1021/jm900481c Prostaglandin G/H synthase 1 1
18459759 10.1021/jm800197b Arachidonate 5-lipoxygenase-activating protein 1
18459759 10.1021/jm800197b Prostaglandin E synthase 2 1
18459759 10.1021/jm800197b Unchecked 1
15953724 10.1016/j.bmcl.2005.05.027 Unchecked 1
15953724 10.1016/j.bmcl.2005.05.027 Arachidonate 5-lipoxygenase-activating protein 1
15953724 10.1016/j.bmcl.2005.05.027 Thromboxane-A synthase 1

Data from ChEMBL 36 via Core Engine