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Compound Detail

CHEMBL25725

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COc1ccc2c(c1)c(CC(=O)NCCCO)c(C)n2C(=O)c1ccc(Cl)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL25725
Phase Preclinical
Structure Type MOL
InChI Key JKOWVRMWEPTPOD-UHFFFAOYSA-N
9
Targets
13
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

414.9
MW (Da)
3.34
ALogP
5
HBA
2
HBD
80.6
PSA (Ų)
0.58
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H23ClN2O4
MW 414.89
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.94

Activity Summary

IC50 11 meas. best 6.66
EC50 1 meas. best 5.11
Ki 1 meas. best 5.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 6.66 6.205 220.0 2
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 5.48 5.48 3300.0 1
Histamine H4 receptor
CHEMBL3759
 EC50 5.11 5.11 7780.0 1
Histamine H4 receptor
CHEMBL3759
 Ki 5.11 5.11 7780.0 1
MCF7
CHEMBL387
 IC50 4.66 4.66 22000.0 1
HeLa
CHEMBL399
 IC50 4.58 4.58 26000.0 1
MIA PaCa-2
CHEMBL614725
 IC50 4.36 4.36 44000.0 1
SW-620
CHEMBL612262
 IC50 4.33 4.33 47000.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 4.19 4.19 64000.0 1
CCRF-CEM
CHEMBL382
 IC50 4.11 4.11 78000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 2 IC50 = 220.0 nM 6.66 Inhibitory concentration against human prostaglandin G/H synthase 2 11965379
Prostaglandin G/H synthase 2 IC50 = 1800.0 nM 5.75 Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromb... 17994684
Prostaglandin G/H synthase 1 IC50 = 3300.0 nM 5.48 Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thr... 17994684
Histamine H4 receptor EC50 = 7780.0 nM 5.11 Agonist activity at human H4 receptor expressed in CHO cell membranes co-express... 27718472
Histamine H4 receptor Ki = 7780.0 nM 5.11 Agonist activity at human H4 receptor expressed in CHO cell membranes co-express... 27718472
MCF7 IC50 = 22000.0 nM 4.66 Cytostatic activity against human MCF7 cells after 72 hrs by MTT assay 18485540
HeLa IC50 = 26000.0 nM 4.58 Cytostatic activity against human HeLa cells after 72 hrs by MTT assay 18485540
MIA PaCa-2 IC50 = 44000.0 nM 4.36 Cytostatic activity against human MIAPaCa2 cells after 72 hrs by MTT assay 18485540
SW-620 IC50 = 47000.0 nM 4.33 Cytostatic activity against human SW620 cells after 72 hrs by MTT assay 18485540
Prostaglandin G/H synthase 1 IC50 = 64000.0 nM 4.19 Inhibitory concentration against prostaglandin G/H synthase 1 11965379
CCRF-CEM IC50 = 78000.0 nM 4.11 Cytostatic activity against human CEM cells after 72 hrs by MTT assay 18485540

Literature References

PubMed DOI Target Context # Activities
17994684 10.1021/jm0611861 Prostaglandin G/H synthase 1 6
17994684 10.1021/jm0611861 Prostaglandin G/H synthase 2 6
17994684 10.1021/jm0611861 Rattus norvegicus 3
27718472 10.1016/j.ejmech.2016.09.074 Histamine H4 receptor 3
18485540 10.1016/j.ejmech.2008.03.037 Vesicular stomatitis virus 2
18485540 10.1016/j.ejmech.2008.03.037 Coxsackievirus B4 2
18485540 10.1016/j.ejmech.2008.03.037 MIA PaCa-2 1
18485540 10.1016/j.ejmech.2008.03.037 Human alphaherpesvirus 1 1
18485540 10.1016/j.ejmech.2008.03.037 Human immunodeficiency virus 2 1
18485540 10.1016/j.ejmech.2008.03.037 ADMET 1
18485540 10.1016/j.ejmech.2008.03.037 NCI-H460 1
18485540 10.1016/j.ejmech.2008.03.037 L1210 1
18485540 10.1016/j.ejmech.2008.03.037 NON-PROTEIN TARGET 1
18485540 10.1016/j.ejmech.2008.03.037 CCRF-CEM 1
11965379 10.1016/s0960-894x(02)00133-6 Prostaglandin G/H synthase 1 1
18485540 10.1016/j.ejmech.2008.03.037 HeLa 1
18485540 10.1016/j.ejmech.2008.03.037 MCF7 1
18485540 10.1016/j.ejmech.2008.03.037 SW-620 1
17994684 10.1021/jm0611861 Unchecked 1
11965379 10.1016/s0960-894x(02)00133-6 Cyclooxygenase 1

Data from ChEMBL 36 via Core Engine