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Compound Detail

CHEMBL56543

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N#C/C(=C\c1ccc(O)c(O)c1)C(=O)NCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL56543
Phase Preclinical
Structure Type MOL
InChI Key TUCIOBMMDDOEMM-RIYZIHGNSA-N
12
Targets
30
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

294.3
MW (Da)
2.32
ALogP
4
HBA
3
HBD
93.3
PSA (Ų)
0.46
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H14N2O3
MW 294.31
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.50

Activity Summary

IC50 29 meas. best 7.0
EC50 1 meas. best 4.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 IC50 7.0 6.165 100.0 8
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 5.47 5.47 3380.0 1
T-cell
CHEMBL614309
 IC50 5.43 5.43 3750.0 1
HFF
CHEMBL614071
 IC50 5.25 5.25 5584.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.12 5.12 7560.0 1
Unchecked
CHEMBL612545
 IC50 5.11 5.11 7700.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.0 4.9857 10000.0 7
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 4.87 4.87 13489.6 3
Glutamate NMDA receptor; Grin1/Grin2a
CHEMBL2096680
 IC50 4.72 4.72 19000.0 1
Unchecked
CHEMBL612545
 EC50 4.57 4.57 27120.0 1
Glutamate NMDA receptor; Grin1/Grin2b
CHEMBL2096666
 IC50 4.35 4.35 45000.0 1
HT-29
CHEMBL384
 IC50 4.11 4.11 78523.0 1
Glutamate NMDA receptor; Grin1/Grin2c
CHEMBL2096911
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor IC50 = 100.0 nM 7.0 Inhibition of Epidermal growth factor receptor autophosphorylation 10464027
Epidermal growth factor receptor IC50 = 100.0 nM 7.0 In vitro inhibition of HER1 autophosphorylation. 1676428
Epidermal growth factor receptor IC50 = 100.0 nM 7.0 Inhibition of EGFR autophosphorylation 18077363
Epidermal growth factor receptor IC50 = 501.19 nM 6.3 Inhibitory activity against epidermal growth factor receptor (EGFR) 14561085
Epidermal growth factor receptor IC50 = 2000.0 nM 5.7 Inhibition of polyGAT phosphorylation 1676428
Epidermal growth factor receptor IC50 = 2000.0 nM 5.7 Inhibition of EGFR in human A431 cells 1479375
Tyrosine-protein kinase JAK1 IC50 = 3380.0 nM 5.47 Inhibition of JAK1 14593182
Epidermal growth factor receptor IC50 = 3500.0 nM 5.46 Inhibition of HER14 (human EGFR overexpressing) cell proliferation. 1676428
T-cell IC50 = 3750.0 nM 5.43 Inhibition of IL2-induced proliferation of human T cells assessed as [3H]thymidi... 14593182
HFF IC50 = 5584.0 nM 5.25 Inhibition of fetal calf serum-induced proliferation of human foreskin fibroblas... 14593182
Epidermal growth factor receptor IC50 = 7000.0 nM 5.16 Inhibition of EGF-dependent proliferation of human and guinea pig keratinocytes;... 11462969
NON-PROTEIN TARGET IC50 = 7560.0 nM 5.12 Inhibition of human GM-CSF-induced proliferation in human HUO3 cells assessed as... 14593182
Unchecked IC50 = 7700.0 nM 5.11 PUBCHEM_BIOASSAY: A biochemical assay using the ADP-Hunter methodology, purified... -
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
33691794 10.1186/s13148-021-01037-1 A549 4
21185195 10.1016/j.bmc.2010.11.057 Tyrosine-protein kinase JAK2 4
23398362 10.1042/bj20121418 cGMP-dependent protein kinase 1 4
23398362 10.1042/bj20121418 Serine/threonine-protein kinase mTOR 4
23398362 10.1042/bj20121418 Tyrosine-protein kinase HCK 4
23398362 10.1042/bj20121418 Cyclin-dependent kinase 5/CDK5 activator 1 4
23398362 10.1042/bj20121418 Tyrosine-protein kinase Lck 4
23398362 10.1042/bj20121418 Insulin-like growth factor 1 receptor 4
23398362 10.1042/bj20121418 Insulin receptor 4
23398362 10.1042/bj20121418 Protein kinase C beta type 4
1676428 10.1021/jm00110a022 Epidermal growth factor receptor 3
35544345 10.1021/acs.jnatprod.2c00098 B16 3
21185195 10.1016/j.bmc.2010.11.057 HT-29 3
18578470 10.1021/jm701271y U-266 3
35544345 10.1021/acs.jnatprod.2c00098 A-375 3
23398362 10.1042/bj20121418 Fibroblast growth factor receptor 3 2
23398362 10.1042/bj20121418 Fibroblast growth factor receptor 4 2
23398362 10.1042/bj20121418 Death-associated protein kinase 1 2
23398362 10.1042/bj20121418 Casein kinase I isoform delta 2

Data from ChEMBL 36 via Core Engine