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Compound Detail

CHEMBL181529

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COc1cc(/C=C/c2cc(/C=C/c3ccc(O)c(OC)c3)on2)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL181529
Phase Preclinical
Structure Type MOL
InChI Key MRBBFOWSPXHYQT-FCXRPNKRSA-N
12
Targets
29
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

365.4
MW (Da)
4.44
ALogP
6
HBA
2
HBD
85.0
PSA (Ų)
0.67
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H19NO5
MW 365.39
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness 0.15

Activity Summary

IC50 26 meas. best 6.86
EC50 3 meas. best 5.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Amyloid-beta precursor protein
CHEMBL2487
 IC50 6.86 6.005 138.0 4
Calcium/calmodulin-dependent protein kinase type II subunit alpha
CHEMBL4147
 IC50 6.17 5.115 680.0 4
MCF7
CHEMBL387
 IC50 5.75 5.17 1760.0 3
Protein kinase C theta type
CHEMBL3920
 EC50 5.5 5.5 3160.0 1
SK-BR-3
CHEMBL613834
 IC50 5.4 5.4 4000.0 1
Unchecked
CHEMBL612545
 IC50 5.21 4.745 6100.0 8
Plasmodium falciparum
CHEMBL364
 IC50 5.1 5.085 7920.0 2
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 4.97 4.97 10710.0 1
Protein kinase C delta type
CHEMBL2996
 EC50 4.94 4.94 11550.0 1
Protein kinase C epsilon type
CHEMBL3582
 EC50 4.93 4.93 11810.0 1
MCF7R
CHEMBL614327
 IC50 4.92 4.92 12000.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.89 4.89 12800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Amyloid-beta precursor protein IC50 = 138.0 nM 6.86 Displacement of [125I]IMPY from fibrillar amyloid beta 42 (unknown origin) after... 29798827
Amyloid-beta precursor protein IC50 = 138.0 nM 6.86 Inhibition of amyloid beta 42 transfected in human H4 cells incubated for 20 to ... 33548635
Calcium/calmodulin-dependent protein kinase type II subunit alpha IC50 = 680.0 nM 6.17 Inhibition of autophosphorylated alphaCaMK2 using GST-NR2A as substrate incubate... 22989913
MCF7 IC50 = 1760.0 nM 5.75 Antiproliferative activity against human MCF7 cells after 72 hrs by MTS-PMS assa... 19019687
Protein kinase C theta type EC50 = 3160.0 nM 5.5 Binding affinity to PKCtheta C1B subdomain after 1 hr by fluorescence quenching ... 21975067
SK-BR-3 IC50 = 4000.0 nM 5.4 Antiproliferative activity against human SKBR3 cells after 72 hrs by MTS-PMS ass... 19019687
Unchecked IC50 = 6100.0 nM 5.21 Inhibition of amyloid beta 38 secretion transfected in human H4 cells incubated ... 33548635
Amyloid-beta precursor protein IC50 = 6800.0 nM 5.17 Inhibition of amyloid beta 42 secretion transfected in human H4 cells incubated ... 33548635
Amyloid-beta precursor protein IC50 = 7400.0 nM 5.13 Inhibition of amyloid beta 40 secretion transfected in human H4 cells incubated ... 33548635
Plasmodium falciparum IC50 = 7920.0 nM 5.1 Antimalarial activity against chloroquine-resistant Plasmodium falciparum MP14 18194869
Plasmodium falciparum IC50 = 8440.0 nM 5.07 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum FCK2 18194869
Prostaglandin G/H synthase 2 IC50 = 10710.0 nM 4.97 Anti-oxidant activity in DPPH radicak scavenging assay; n=3-4 15780608
Protein kinase C delta type EC50 = 11550.0 nM 4.94 Binding affinity to PKCdelta C1B subdomain after 1 hr by fluorescence quenching ... 21975067
Calcium/calmodulin-dependent protein kinase type II subunit alpha IC50 = 11370.0 nM 4.94 Inhibition of alphaCaMK2 using GST-NR2A as substrate incubated for 1 min prior t... 22989913
Protein kinase C epsilon type EC50 = 11810.0 nM 4.93 Binding affinity to PKCepsilon C1B subdomain after 1 hr by fluorescence quenchin... 21975067
MCF7R IC50 = 12000.0 nM 4.92 Growth inhibition of human multidrug-resistant MCF7R cells after 48 hrs by MTS a... 18039573
MCF7R IC50 = 12000.0 nM 4.92 Cytotoxicity against human MCF7R cells assessed as cell growth inhibition and by... 34000484
NON-PROTEIN TARGET IC50 = 12800.0 nM 4.89 Growth inhibition of human HA22T/VGH cells after 48 hrs by MTS assay 18039573
MCF7 IC50 = 13100.0 nM 4.88 Growth inhibition of human MCF7 cells after 48 hrs by MTS assay 18039573
MCF7 IC50 = 13100.0 nM 4.88 Cytotoxicity against human MCF7 cells assessed as cell growth inhibition and mea... 34000484

Literature References

PubMed DOI Target Context # Activities
22989913 10.1016/j.bmc.2012.08.029 Unchecked 6
18194869 10.1016/j.bmc.2007.12.054 Plasmodium falciparum 4
22989913 10.1016/j.bmc.2012.08.029 Calcium/calmodulin-dependent protein kinase type II subunit alpha 4
33548635 10.1016/j.ejmech.2021.113209 Amyloid-beta precursor protein 3
15780608 10.1016/j.bmcl.2005.02.039 Prostaglandin G/H synthase 2 3
18039573 10.1016/j.bmcl.2007.11.021 NON-PROTEIN TARGET 2
18039573 10.1016/j.bmcl.2007.11.021 MCF7 2
18039573 10.1016/j.bmcl.2007.11.021 MCF7R 2
33548635 10.1016/j.ejmech.2021.113209 Microtubule-associated protein tau 2
31336310 10.1016/j.ejmech.2019.07.034 MCF7R 2
21975067 10.1016/j.bmc.2011.09.011 Unchecked 2
21975067 10.1016/j.bmc.2011.09.011 Protein kinase C delta type 1
34000484 10.1016/j.ejmech.2021.113511 MCF7 1
29798827 10.1016/j.bmcl.2018.05.032 Amyloid-beta precursor protein 1
21975067 10.1016/j.bmc.2011.09.011 Protein kinase C theta type 1
21975067 10.1016/j.bmc.2011.09.011 Protein kinase C epsilon type 1
21830815 10.1021/jm2004046 Unchecked 1
20691508 10.1016/j.ejmech.2010.07.003 Mycobacterium tuberculosis 1
19019687 10.1016/j.bmc.2008.10.057 SK-BR-3 1
19019687 10.1016/j.bmc.2008.10.057 MCF7 1

Data from ChEMBL 36 via Core Engine