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Compound Detail

CHEMBL3298000

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COc1ccc(N(C)c2nc(C)nc3oc(C)cc23)cc1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3298000
Phase Preclinical
Structure Type MOL
InChI Key WZIIUILMMRGPJL-UHFFFAOYSA-N
Parent Compound CHEMBL3297898
Active Moiety CHEMBL3297898
14
Targets
18
Activities
2
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

283.3
MW (Da)
3.62
ALogP
5
HBA
0
HBD
51.4
PSA (Ų)
0.73
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H18ClN3O2
MW 319.79
Aromatic Rings 3
Heavy Atoms 21
NP-Likeness -0.86

Activity Summary

IC50 17 meas. best 8.43
EC50 1 meas. best 6.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Chorioallantoic membrane
CHEMBL2367390
 IC50 8.43 8.43 3.7 1
MDA-MB-468
CHEMBL614335
 IC50 8.15 8.15 7.1 1
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 7.7 7.7 20.2 1
Platelet-derived growth factor receptor beta
CHEMBL1913
 IC50 7.66 7.66 21.9 1
HeLa
CHEMBL399
 IC50 7.39 7.37 40.6 2
MDA-MB-435
CHEMBL614697
 IC50 7.33 7.305 47.0 2
SK-OV-3
CHEMBL614925
 IC50 7.3 7.255 50.4 2
A-431
CHEMBL614069
 IC50 7.25 7.25 55.8 1
Epidermal growth factor receptor
CHEMBL203
 IC50 7.08 7.08 82.3 1
4T1
CHEMBL612589
 IC50 7.01 7.01 97.9 1
MCF7
CHEMBL387
 IC50 6.89 6.875 129.8 2
MDA-MB-231
CHEMBL400
 IC50 6.83 6.83 147.6 1
HUVEC
CHEMBL613979
 IC50 6.76 6.76 172.2 1
Tubulin
CHEMBL2111354
 EC50 6.24 6.24 570.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Chorioallantoic membrane IC50 = 3.7 nM 8.43 Antiangiogenic activity in fertile leghorn chicken egg Chorioallantoic membrane ... 24890652
MDA-MB-468 IC50 = 7.1 nM 8.15 Cytotoxicity against human triple negative MDA-MB-468 cells 24890652
Vascular endothelial growth factor receptor 2 IC50 = 20.2 nM 7.7 Inhibition of VEGFR2 in human U251 cells by phosphotyrosine ELISA assay 24890652
Platelet-derived growth factor receptor beta IC50 = 21.9 nM 7.66 Inhibition of PDGFRbeta in human SH-SY5Y cells by phosphotyrosine ELISA assay 24890652
HeLa IC50 = 40.6 nM 7.39 Antiproliferative activity against human HeLa cells 24890652
HeLa IC50 = 44.7 nM 7.35 Antiproliferative activity against human HeLa cells expressing beta3-tubulin 24890652
MDA-MB-435 IC50 = 47.0 nM 7.33 Antiproliferative activity against human MDA-MB-435 cells 24890652
SK-OV-3 IC50 = 50.4 nM 7.3 Antiproliferative activity against human SKOV3 cells 24890652
MDA-MB-435 IC50 = 53.0 nM 7.28 Cytotoxicity against human MDA-MB-435 cells 24890652
A-431 IC50 = 55.8 nM 7.25 Cytotoxicity against human A431 cells by SRB assay 24890652
SK-OV-3 IC50 = 62.1 nM 7.21 Antiproliferative activity against human SKOV3 cells expressing MDR1/M-6-6 24890652
Epidermal growth factor receptor IC50 = 82.3 nM 7.08 Inhibition of EGFR in human A431 cells by phosphotyrosine ELISA assay 24890652
4T1 IC50 = 97.9 nM 7.01 Cytotoxicity against mouse triple negative 4T1 cells 24890652
MCF7 IC50 = 129.8 nM 6.89 Cytotoxicity against human taxoid-resistant MCF7 cells 24890652
MCF7 IC50 = 137.7 nM 6.86 Cytotoxicity against human ER-positive MCF7 cells 24890652
MDA-MB-231 IC50 = 147.6 nM 6.83 Cytotoxicity against human triple negative MDA-MB-231 cells 24890652
HUVEC IC50 = 172.2 nM 6.76 Cytotoxicity against HUVEC 24890652
Tubulin EC50 = 570.0 nM 6.24 Induction of pig brain tubulin depolymerization by spectrophotometric analysis 24890652

Literature References

PubMed DOI Target Context # Activities
24890652 10.1016/j.bmc.2014.04.049 HeLa 5
24890652 10.1016/j.bmc.2014.04.049 MDA-MB-435 4
24890652 10.1016/j.bmc.2014.04.049 4T1 4
24890652 10.1016/j.bmc.2014.04.049 Mus musculus 3
24890652 10.1016/j.bmc.2014.04.049 SK-OV-3 3
24890652 10.1016/j.bmc.2014.04.049 Tubulin 2
24890652 10.1016/j.bmc.2014.04.049 MCF7 2
24890652 10.1016/j.bmc.2014.04.049 Chorioallantoic membrane 1
24890652 10.1016/j.bmc.2014.04.049 MDA-MB-468 1
24890652 10.1016/j.bmc.2014.04.049 HUVEC 1
24890652 10.1016/j.bmc.2014.04.049 MDA-MB-231 1
24890652 10.1016/j.bmc.2014.04.049 Platelet-derived growth factor receptor beta 1
24890652 10.1016/j.bmc.2014.04.049 Vascular endothelial growth factor receptor 2 1
24890652 10.1016/j.bmc.2014.04.049 A-431 1
24890652 10.1016/j.bmc.2014.04.049 Epidermal growth factor receptor 1

Data from ChEMBL 36 via Core Engine