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Compound Detail

CHEMBL4778826

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COc1ccc(/C=C/C(=O)c2nnn(-c3ccc(Cl)cc3)c2C)cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4778826
Phase Preclinical
Structure Type MOL
InChI Key YOJHPSLHBFFDDL-ONNFQVAWSA-N
18
Targets
25
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

383.8
MW (Da)
4.14
ALogP
6
HBA
0
HBD
66.2
PSA (Ų)
0.47
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H18ClN3O3
MW 383.83
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.16

Activity Summary

IC50 25 meas. best 8.01

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tubulin
CHEMBL2095182
 IC50 8.01 8.01 9.8 1
Unchecked
CHEMBL612545
 IC50 7.73 5.54 18.6 5
Epidermal growth factor receptor
CHEMBL203
 IC50 7.44 7.44 36.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 7.33 7.33 47.0 1
Transcription factor p65
CHEMBL5533
 IC50 6.87 6.87 134.0 1
MCF7
CHEMBL387
 IC50 6.62 6.62 240.0 1
HCT-116
CHEMBL394
 IC50 6.58 6.58 260.0 1
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 6.41 6.41 388.0 1
RPMI-8226
CHEMBL614882
 IC50 6.19 6.19 640.0 2
M14
CHEMBL614317
 IC50 6.16 6.16 690.0 1
K562
CHEMBL385
 IC50 6.08 6.08 840.0 2
SR
CHEMBL614300
 IC50 6.02 6.02 960.0 1
Histone deacetylase 1
CHEMBL325
 IC50 5.82 5.82 1530.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 5.54 5.54 2900.0 1
PC-3
CHEMBL390
 IC50 5.53 5.53 2950.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 5.52 5.52 3000.0 1
CCD-18Co
CHEMBL4296405
 IC50 4.77 4.77 17150.0 1
MCF-10A
CHEMBL614321
 IC50 4.6 4.6 25000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tubulin IC50 = 9.77 nM 8.01 Inhibition of Tubulin in human RPMI-8226 cells incubated for 2 hrs by ELISA 31986406
Unchecked IC50 = 18.6 nM 7.73 Inhibition of Topoisomerase 2 in human RPMI-8226 cells incubated for 2 hrs by EL... 31986406
Epidermal growth factor receptor IC50 = 36.0 nM 7.44 Inhibition of EGFR in human RPMI-8226 cells incubated for 2 hrs by ELISA 31986406
Histone deacetylase 8 IC50 = 47.0 nM 7.33 Inhibition of HDAC8 in human RPMI-8226 cells incubated for 2 hrs by ELISA 31986406
Transcription factor p65 IC50 = 134.0 nM 6.87 Inhibition of NFkappaB p65 in human RPMI-8226 cells incubated for 2 hrs by ELISA 31986406
MCF7 IC50 = 240.0 nM 6.62 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability in... 31986406
HCT-116 IC50 = 260.0 nM 6.58 Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability... 31986406
Vascular endothelial growth factor receptor 2 IC50 = 388.0 nM 6.41 Inhibition of VEGFR2 in human RPMI-8226 cells incubated for 2 hrs by ELISA 31986406
RPMI-8226 IC50 = 640.0 nM 6.19 Cytotoxicity against human RPMI-8226 cells assessed as reduction in cell viabili... 31986406
RPMI-8226 IC50 = 640.0 nM 6.19 Antiproliferative activity against human RPMI-8226 cells 38889607
M14 IC50 = 690.0 nM 6.16 Cytotoxicity against human M14 cells assessed as reduction in cell viability inc... 31986406
K562 IC50 = 840.0 nM 6.08 Antiproliferative activity against human K562 cells 38889607
K562 IC50 = 840.0 nM 6.08 Cytotoxicity against human K562 cells assessed as reduction in cell viability in... 31986406
SR IC50 = 960.0 nM 6.02 Cytotoxicity against human SR cells assessed as reduction in cell viability incu... 31986406
Unchecked IC50 = 960.0 nM 6.02 Cytotoxicity against human Leukemia cancer cells 38889607
Histone deacetylase 1 IC50 = 1530.0 nM 5.82 Inhibition of HDAC1 in human RPMI-8226 cells incubated for 2 hrs by ELISA 31986406
Histone deacetylase 2 IC50 = 2900.0 nM 5.54 Inhibition of HDAC2 in human RPMI-8226 cells incubated for 2 hrs by ELISA 31986406
PC-3 IC50 = 2950.0 nM 5.53 Cytotoxicity against human PC-3 cells assessed as reduction in cell viability in... 31986406
Histone deacetylase 3 IC50 = 3000.0 nM 5.52 Inhibition of HDAC3 in human RPMI-8226 cells incubated for 2 hrs by ELISA 31986406
Unchecked IC50 = 12880.0 nM 4.89 Cytotoxicity against human HPrEC cells assessed as reduction in cell viability i... 31986406

Literature References

PubMed DOI Target Context # Activities
31986406 10.1016/j.ejmech.2020.112062 RPMI-8226 39
31986406 10.1016/j.ejmech.2020.112062 Unchecked 11
31986406 10.1016/j.ejmech.2020.112062 PC-3 2
31986406 10.1016/j.ejmech.2020.112062 K562 2
31986406 10.1016/j.ejmech.2020.112062 MCF7 2
31986406 10.1016/j.ejmech.2020.112062 SR 2
31986406 10.1016/j.ejmech.2020.112062 HCT-116 2
31986406 10.1016/j.ejmech.2020.112062 M14 2
31986406 10.1016/j.ejmech.2020.112062 KM12 1
31986406 10.1016/j.ejmech.2020.112062 OVCAR-3 1
31986406 10.1016/j.ejmech.2020.112062 IGROV-1 1
31986406 10.1016/j.ejmech.2020.112062 SK-MEL-5 1
31986406 10.1016/j.ejmech.2020.112062 MDA-MB-435 1
31986406 10.1016/j.ejmech.2020.112062 LOX IMVI 1
31986406 10.1016/j.ejmech.2020.112062 SW-620 1
31986406 10.1016/j.ejmech.2020.112062 CCRF-CEM 1
38889607 10.1016/j.ejmech.2024.116578 Unchecked 1
31986406 10.1016/j.ejmech.2020.112062 HCT-15 1
31986406 10.1016/j.ejmech.2020.112062 NCI-H226 1
31986406 10.1016/j.ejmech.2020.112062 MOLT-4 1

Data from ChEMBL 36 via Core Engine