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Compound Detail

CHEMBL180650

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Cc1ccccc1-c1ccc(-c2ccc3c(c2)c(C)c(CC(C)(C)C(=O)O)n3Cc2ccc(Cl)cc2)cc1F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL180650
Phase Preclinical
Structure Type MOL
InChI Key IYCJVTFMIQICDJ-UHFFFAOYSA-N
5
Targets
20
Activities
1
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

540.1
MW (Da)
9.09
ALogP
2
HBA
1
HBD
42.2
PSA (Ų)
0.22
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 C34H31ClFNO2
MW 540.08
Aromatic Rings 5
Heavy Atoms 39
NP-Likeness -0.65

Activity Summary

IC50 20 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin E synthase 2
CHEMBL4411
 IC50 8.52 8.52 3.0 1
Prostaglandin E synthase
CHEMBL5658
 IC50 8.52 7.3933 3.0 3
Unchecked
CHEMBL612545
 IC50 8.52 7.81 3.0 5
A549
CHEMBL392
 IC50 6.57 5.8022 270.0 9
Thromboxane-A synthase
CHEMBL1835
 IC50 6.02 6.02 950.0 2

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 human recombinant mPGES1 18029174
Unchecked IC50 = 3.0 nM 8.52 Inhibition of mPGES1 18459759
Unchecked IC50 = 3.0 nM 8.52 Inhibition of mPGES1 expressed in human HeLa cells assessed as inhibition of IL-... 20025212
Prostaglandin E synthase IC50 = 3.0 nM 8.52 Inhibition of human microsomal PGES1 in cell-free system assessed as inhibition ... 21466167
Prostaglandin E synthase 2 IC50 = 3.0 nM 8.52 Inhibitory concentration against human prostaglandin E2 synthase (mPGES-1) 15953724
Prostaglandin E synthase IC50 = 23.0 nM 7.64 Inhibition of recombinant human mPGES-1 expressed in human 293E cell microsomes ... 25961169
Unchecked IC50 = 130.0 nM 6.89 Inhibition of rat mPGES1 18029174
Unchecked IC50 = 250.0 nM 6.6 In vitro Inhibition against PGE-2 using IL-1-beta-stimulated human synoviocyte c... 15953724
A549 IC50 = 270.0 nM 6.57 In vitro Inhibition against PGE-2 using IL-1-beta-stimulated A549 epithelial lun... 15953724
A549 IC50 = 270.0 nM 6.57 Inhibition of IL-1-beta-stimulated PGE2 production in human A549 cells in presen... 18029174
A549 IC50 = 300.0 nM 6.52 Inhibition of PGE2 synthesis in human A549 cells 18459759
Thromboxane-A synthase IC50 = 950.0 nM 6.02 In vitro inhibition against human Thromboxane synthase 15953724
Thromboxane-A synthase IC50 = 950.0 nM 6.02 Inhibition of TX synthase 18029174
Prostaglandin E synthase IC50 = 960.0 nM 6.02 Inhibition of purified mPGES-1 (1 to 152) (unknown origin) extracted from deterg... 25961169
A549 IC50 = 2400.0 nM 5.62 In vitro Inhibition against PGF2-alpha using IL-1-beta-stimulated A549 epithelia... 15953724
A549 IC50 = 2400.0 nM 5.62 Inhibition of IL-1-beta-stimulated PGF2alpha production in human A549 cells in p... 18029174
A549 IC50 = 2400.0 nM 5.62 Inhibition of PGE2alpha synthesis in human A549 cells 18459759
A549 IC50 = 5800.0 nM 5.24 In vitro Inhibition against PGE-2 using IL-1-beta-stimulated A549 epithelial lun... 15953724
A549 IC50 = 5800.0 nM 5.24 Inhibition of IL-1-beta-stimulated PGE2 production in human A549 cells in presen... 18029174
A549 IC50 = 6000.0 nM 5.22 Inhibition of IL1-beta stimulated PGE2 production in human A549 cells 18459759

Literature References

PubMed DOI Target Context # Activities
18029174 10.1016/j.bmcl.2007.10.033 A549 4
25961169 10.1021/acs.jmedchem.5b00330 Prostaglandin E synthase 3
18459759 10.1021/jm800197b A549 3
15953724 10.1016/j.bmcl.2005.05.027 A549 3
18029174 10.1016/j.bmcl.2007.10.033 Blood 2
15953724 10.1016/j.bmcl.2005.05.027 Prostaglandin E synthase 2 2
18029174 10.1016/j.bmcl.2007.10.033 Unchecked 2
18029174 10.1016/j.bmcl.2007.10.033 Prostaglandin E synthase 2 1
18029174 10.1016/j.bmcl.2007.10.033 Thromboxane-A synthase 1
15953724 10.1016/j.bmcl.2005.05.027 Unchecked 1
18459759 10.1021/jm800197b Unchecked 1
18459759 10.1021/jm800197b Prostaglandin E synthase 2 1
18459759 10.1021/jm800197b Arachidonate 5-lipoxygenase-activating protein 1
15953724 10.1016/j.bmcl.2005.05.027 Arachidonate 5-lipoxygenase-activating protein 1
18459759 10.1021/jm800197b Thromboxane-A synthase 1
20025212 10.1021/jm9012505 Unchecked 1
21466167 10.1021/jm101309g Prostaglandin E synthase 1
15953724 10.1016/j.bmcl.2005.05.027 Thromboxane-A synthase 1

Data from ChEMBL 36 via Core Engine