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Compound Detail

CHEMBL1224773

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COc1cc(/C=C2\CN(C)C/C(=C\c3cc(OC)c(OC)c(OC)c3)C2=O)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1224773
Phase Preclinical
Structure Type MOL
InChI Key OGEWTDITEXRGCF-GCBPPVMSSA-N
13
Targets
16
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

469.5
MW (Da)
3.72
ALogP
8
HBA
0
HBD
75.7
PSA (Ų)
0.54
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H31NO7
MW 469.53
Aromatic Rings 2
Heavy Atoms 34
NP-Likeness -0.03

Activity Summary

IC50 13 meas. best 6.41
EC50 2 meas. best 6.52
Kd 1 meas. best 4.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MDA-MB-231
CHEMBL400
 EC50 6.52 6.52 300.0 1
MDA-MB-468
CHEMBL614335
 EC50 6.52 6.52 300.0 1
A549
CHEMBL392
 IC50 6.41 6.09 390.0 2
MDA-MB-231
CHEMBL400
 IC50 6.41 6.41 390.0 1
MV4-11
CHEMBL613835
 IC50 6.41 6.41 390.0 1
MDA-MB-468
CHEMBL614335
 IC50 6.41 6.41 390.0 1
MG-63
CHEMBL614347
 IC50 6.41 6.41 390.0 1
NCI-H23
CHEMBL614997
 IC50 6.41 6.41 390.0 1
SK-BR-3
CHEMBL613834
 IC50 6.4 6.4 400.0 1
Unchecked
CHEMBL612545
 IC50 6.05 6.05 900.0 1
NCI-H460
CHEMBL396
 IC50 6.0 6.0 1000.0 1
NCI-H1975
CHEMBL614348
 IC50 6.0 6.0 1000.0 1
NCI-H1650
CHEMBL1075518
 IC50 5.82 5.82 1500.0 1
L02
CHEMBL4296457
 IC50 4.58 4.58 26400.0 1
Lymphocyte antigen 96
CHEMBL2375202
 Kd 4.22 4.22 59500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MDA-MB-231 EC50 = 300.0 nM 6.52 Cytotoxicity against human MDA-MB-231 cells after 72 hrs by SRB assay 20728364
MDA-MB-468 EC50 = 300.0 nM 6.52 Cytotoxicity against human MDA-MB-468 cells after 72 hrs by SRB assay 20728364
A549 IC50 = 390.0 nM 6.41 Antiproliferative activity against human A549 cells assessed as cell viability b... 32172081
MV4-11 IC50 = 390.0 nM 6.41 Antiproliferative activity against human MV4-11 cells assessed as cell viability... 32172081
MG-63 IC50 = 390.0 nM 6.41 Antiproliferative activity against human MG-63 cells assessed as cell viability ... 32172081
NCI-H23 IC50 = 390.0 nM 6.41 Antiproliferative activity against human NCI-H23 cells assessed as cell viabilit... 32172081
MDA-MB-231 IC50 = 390.0 nM 6.41 Antiproliferative activity against human MDA-MB-231 cells assessed as cell viabi... 32172081
MDA-MB-468 IC50 = 390.0 nM 6.41 Antiproliferative activity against human MDA-MB-468 cells assessed as cell viabi... 32172081
SK-BR-3 IC50 = 400.0 nM 6.4 Cytotoxicity against human SKBR3 cells after 72 hrs by SRB assay 20728364
Unchecked IC50 = 900.0 nM 6.05 Inhibition of NF-kappaB activation in human K562 cells 20728364
NCI-H460 IC50 = 1000.0 nM 6.0 Cytotoxicity against human H460 cells assessed as reduction in cell viability af... 29655083
NCI-H1975 IC50 = 1000.0 nM 6.0 Cytotoxicity against human NCI-H1975 cells assessed as reduction in cell viabili... 29655083
NCI-H1650 IC50 = 1500.0 nM 5.82 Cytotoxicity against human NCI-H1650 cells assessed as reduction in cell viabili... 29655083
A549 IC50 = 1700.0 nM 5.77 Cytotoxicity against human A549 cells assessed as reduction in cell viability af... 29655083
L02 IC50 = 26400.0 nM 4.58 Cytotoxicity against human HL7702 cells assessed as reduction in cell viability ... 29655083
Lymphocyte antigen 96 Kd = 59500.0 nM 4.22 Binding affinity to recombinant human MD2 by SPR analysis 29466778

Literature References

PubMed DOI Target Context # Activities
29655083 10.1016/j.ejmech.2018.03.051 A549 24
29466778 10.1016/j.ejmech.2018.02.008 Rattus norvegicus 13
29466778 10.1016/j.ejmech.2018.02.008 Lymphocyte antigen 96 11
29466778 10.1016/j.ejmech.2018.02.008 Peritoneal macrophage 11
29655083 10.1016/j.ejmech.2018.03.051 Unchecked 4
29466778 10.1016/j.ejmech.2018.02.008 Mitogen-activated protein kinase 1 3
29655083 10.1016/j.ejmech.2018.03.051 Mitogen-activated protein kinase 8/9 3
29466778 10.1016/j.ejmech.2018.02.008 Inhibitor of nuclear factor kappa-B kinase subunit beta 3
29466778 10.1016/j.ejmech.2018.02.008 Interleukin-1 receptor-associated kinase 1 3
20728364 10.1016/j.bmc.2010.07.063 MDA-MB-231 2
29466778 10.1016/j.ejmech.2018.02.008 Unchecked 2
29655083 10.1016/j.ejmech.2018.03.051 NF-kappa-B inhibitor alpha 2
29655083 10.1016/j.ejmech.2018.03.051 L02 1
29655083 10.1016/j.ejmech.2018.03.051 NCI-H1650 1
29655083 10.1016/j.ejmech.2018.03.051 NCI-H460 1
29655083 10.1016/j.ejmech.2018.03.051 Inhibitor of nuclear factor kappa-B kinase subunit beta 1
29223100 10.1016/j.ejmech.2017.11.048 Luciferin 4-monooxygenase 1
29223100 10.1016/j.ejmech.2017.11.048 Nuclear factor erythroid 2-related factor 2 1
32172081 10.1016/j.ejmech.2020.112177 MDA-MB-468 1
20728364 10.1016/j.bmc.2010.07.063 MDA-MB-468 1

Data from ChEMBL 36 via Core Engine