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Compound Detail

CHEMBL440948

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COc1cc(OC)c(C(=O)/C=C/c2ccccc2)c(OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL440948
Phase Preclinical
Structure Type MOL
InChI Key DRGVZVJDZOMQAI-MDZDMXLPSA-N
17
Targets
19
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

298.3
MW (Da)
3.61
ALogP
4
HBA
0
HBD
44.8
PSA (Ų)
0.60
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H18O4
MW 298.34
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness 0.25

Activity Summary

IC50 19 meas. best 7.17

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A498
CHEMBL614516
 IC50 7.17 7.17 67.0 1
A-375
CHEMBL613859
 IC50 7.17 7.17 67.0 1
HeLa
CHEMBL399
 IC50 6.87 6.075 134.0 2
HepG2
CHEMBL395
 IC50 6.87 6.87 134.0 1
A549
CHEMBL392
 IC50 6.87 6.12 134.0 2
HEK293
CHEMBL614818
 IC50 6.47 6.47 335.0 1
Homo sapiens
CHEMBL372
 IC50 5.9 5.9 1250.0 1
PC-3
CHEMBL390
 IC50 5.29 5.29 5100.0 1
Caco-2
CHEMBL614058
 IC50 5.24 5.24 5800.0 1
U-937
CHEMBL612794
 IC50 5.17 5.17 6700.0 1
HCT-116
CHEMBL394
 IC50 5.16 5.16 6900.0 1
RL
CHEMBL2366175
 IC50 5.16 5.16 6900.0 1
HaCaT
CHEMBL614392
 IC50 5.14 5.14 7200.0 1
MCF7
CHEMBL387
 IC50 5.03 5.03 9400.0 1
NCI-H727
CHEMBL1075545
 IC50 4.94 4.94 11400.0 1
MDA-MB-231
CHEMBL400
 IC50 4.89 4.89 12900.0 1
Huh-7
CHEMBL614039
 IC50 4.81 4.81 15500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
A-375 IC50 = 67.0 nM 7.17 Antiproliferative activity against human A375 cells 27217001
A498 IC50 = 67.0 nM 7.17 Antiproliferative activity against human A498 cells 27217001
HeLa IC50 = 134.0 nM 6.87 Antiproliferative activity against human HeLa cells 27217001
A549 IC50 = 134.0 nM 6.87 Antiproliferative activity against human A549 cells 27217001
HepG2 IC50 = 134.0 nM 6.87 Antiproliferative activity against human HepG2 cells 27217001
HEK293 IC50 = 335.0 nM 6.47 Cytotoxicity activity against HEK293 cells 27217001
Homo sapiens IC50 = 1250.0 nM 5.9 Inhibition of the production of Interleukin-1-beta from human peripheral blood m... 8496911
A549 IC50 = 4300.0 nM 5.37 Cytotoxicity against human A549 cells assessed as reduction in cell viability in... 31673309
PC-3 IC50 = 5100.0 nM 5.29 Cytotoxicity against human PC3 cells assessed as cell viability after 48 hrs by ... 28214231
HeLa IC50 = 5200.0 nM 5.28 Cytotoxicity against human HeLa cells assessed as reduction in cell viability in... 31673309
Caco-2 IC50 = 5800.0 nM 5.24 Cytotoxicity against human Caco2 cells assessed as cell viability after 48 hrs b... 28214231
U-937 IC50 = 6700.0 nM 5.17 Cytotoxicity against human U937 cells assessed as reduction in cell viability in... 31673309
HCT-116 IC50 = 6900.0 nM 5.16 Cytotoxicity against human HCT116 cells assessed as cell viability after 48 hrs ... 28214231
RL IC50 = 6900.0 nM 5.16 Cytotoxicity against human RL assessed as cell viability after 48 hrs by Hoechst... 28214231
HaCaT IC50 = 7200.0 nM 5.14 Cytotoxicity against human HaCaT cells assessed as cell viability after 48 hrs b... 28214231
MCF7 IC50 = 9400.0 nM 5.03 Cytotoxicity against human MCF7 assessed as cell viability after 48 hrs by Hoech... 28214231
NCI-H727 IC50 = 11400.0 nM 4.94 Cytotoxicity against human NCI-H727 cells assessed as cell viability after 48 hr... 28214231
MDA-MB-231 IC50 = 12900.0 nM 4.89 Cytotoxicity against human MDA-MB-231 cells assessed as cell viability after 48 ... 28214231
Huh-7 IC50 = 15500.0 nM 4.81 Cytotoxicity against human HuH7 cells assessed as cell viability after 48 hrs by... 28214231

Literature References

PubMed DOI Target Context # Activities
28214231 10.1016/j.bmc.2017.01.049 HCT-116 12
28214231 10.1016/j.bmc.2017.01.049 PC-3 11
28214231 10.1016/j.bmc.2017.01.049 MDA-MB-231 11
28214231 10.1016/j.bmc.2017.01.049 Unchecked 9
28214231 10.1016/j.bmc.2017.01.049 HaCaT 7
28214231 10.1016/j.bmc.2017.01.049 NCI-H727 7
28214231 10.1016/j.bmc.2017.01.049 Caco-2 7
28214231 10.1016/j.bmc.2017.01.049 Huh-7 6
27217001 10.1016/j.bmcl.2016.04.096 ADMET 5
28214231 10.1016/j.bmc.2017.01.049 MCF7 5
22239485 10.1021/jm2016073 MCF7 2
28214231 10.1016/j.bmc.2017.01.049 Fibroblast 2
21539383 10.1021/jm2002348 Nuclear factor erythroid 2-related factor 2 2
27217001 10.1016/j.bmcl.2016.04.096 HepG2 1
8496911 10.1021/jm00062a016 Homo sapiens 1
27217001 10.1016/j.bmcl.2016.04.096 A-375 1
27217001 10.1016/j.bmcl.2016.04.096 HEK293 1
27217001 10.1016/j.bmcl.2016.04.096 A549 1
27217001 10.1016/j.bmcl.2016.04.096 A498 1
27217001 10.1016/j.bmcl.2016.04.096 HeLa 1

Data from ChEMBL 36 via Core Engine