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Compound Detail

CHEMBL9859

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COc1ccc(/C=C(\C)C(=O)c2cc(OC)c(OC)c(OC)c2)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL9859
Phase Preclinical
Structure Type MOL
InChI Key ZCMJTMRUBOCGSY-XYOKQWHBSA-N
15
Targets
28
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

358.4
MW (Da)
3.71
ALogP
6
HBA
1
HBD
74.2
PSA (Ų)
0.60
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H22O6
MW 358.39
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.45

Activity Summary

IC50 28 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
K562
CHEMBL385
 IC50 9.7 8.9633 0.2 6
HepG2
CHEMBL395
 IC50 9.68 9.68 0.2 1
SH-SY5Y
CHEMBL614910
 IC50 9.68 9.68 0.2 1
HeLa
CHEMBL399
 IC50 9.21 8.755 0.6 2
A2780
CHEMBL614004
 IC50 8.74 8.63 1.8 2
A549
CHEMBL392
 IC50 8.4 7.4067 4.0 3
MCF7
CHEMBL387
 IC50 8.3 8.3 5.0 1
PC-3
CHEMBL390
 IC50 8.05 8.05 9.0 1
L1210
CHEMBL386
 IC50 7.96 7.96 11.0 1
P388
CHEMBL389
 IC50 7.58 7.58 26.0 1
Tubulin beta-1 chain
CHEMBL1915
 IC50 6.34 6.34 460.0 1
Unchecked
CHEMBL612545
 IC50 6.34 5.9775 460.0 4
Tubulin
CHEMBL2095182
 IC50 6.3 6.025 500.0 2
Tubulin alpha chain
CHEMBL3658
 IC50 6.3 6.3 500.0 1
SGC-7901
CHEMBL614909
 IC50 5.69 5.69 2060.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
K562 IC50 = 0.2 nM 9.7 Inhibitory activity against K562 human chronic myelogenous leukemia cell line us... 14552774
K562 IC50 = 0.21 nM 9.68 Compound was evaluated for cytotoxic activity against K562 human chronic myeloge... 9871706
K562 IC50 = 0.21 nM 9.68 Cytotoxicity against human K562 cells after 5 days by MTT assay 16949281
K562 IC50 = 0.21 nM 9.68 Cytotoxicity against human K562 cells 19837594
K562 IC50 = 0.21 nM 9.68 Antiproliferative activity against human K562 cells after 5 days by MTT assay 19837593
SH-SY5Y IC50 = 0.21 nM 9.68 Cytotoxicity against human SH-SY5Y cells after 48 hrs by MTT assay 21167709
HepG2 IC50 = 0.21 nM 9.68 Antiproliferative activity against human HepG2 cells after 48 hrs by MTT assay 21816517
HeLa IC50 = 0.62 nM 9.21 Compound was evaluated for cytotoxic activity against HeLa S3 cell line 9871706
A2780 IC50 = 1.8 nM 8.74 Antiproliferative activity against human A2780 cells after 5 days by MTT assay 19837594
A2780 IC50 = 3.0 nM 8.52 Antiproliferative activity against human A2780 cells after 48 hrs by MTT assay 28404525
A549 IC50 = 4.0 nM 8.4 Antiproliferative activity against human A549 cells after 48 hrs by MTT assay 28404525
HeLa IC50 = 5.0 nM 8.3 Antiproliferative activity against human HeLa cells after 48 hrs by MTT assay 28404525
MCF7 IC50 = 5.0 nM 8.3 Antiproliferative activity against human MCF7 cells after 48 hrs by MTT assay 28404525
PC-3 IC50 = 9.0 nM 8.05 Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay 28404525
A549 IC50 = 10.0 nM 8.0 Antiproliferative activity against human A549 cells after 5 days by MTT assay 19837594
L1210 IC50 = 11.0 nM 7.96 Antiproliferative activity against mouse L1210 cells after 5 days by MTT assay 19837594
P388 IC50 = 26.0 nM 7.58 Antiproliferative activity against mouse P388 cells after 5 days by MTT assay 19837594
Tubulin beta-1 chain IC50 = 460.0 nM 6.34 Concentration required for 50% inhibition of tubulin polymerization 15658859
Unchecked IC50 = 460.0 nM 6.34 Inhibition of tubulin assembly by immunofluorescence assay 19837594
Unchecked IC50 = 460.0 nM 6.34 Inhibition of tubulin assembly by Woods method 19837593

Literature References

PubMed DOI Target Context # Activities
19837594 10.1016/j.bmc.2009.09.044 K562 5
19837593 10.1016/j.bmc.2009.09.039 K562 4
19837593 10.1016/j.bmc.2009.09.039 Unchecked 4
14552774 10.1016/j.bmcl.2003.07.003 K562 4
19837594 10.1016/j.bmc.2009.09.044 Unchecked 2
19837594 10.1016/j.bmc.2009.09.044 A2780 1
30739824 10.1016/j.ejmech.2019.01.078 Tubulin 1
28404525 10.1016/j.bmc.2017.03.066 A549 1
21816517 10.1016/j.ejmech.2011.07.016 HepG2 1
21167709 10.1016/j.bmcl.2010.11.113 Unchecked 1
21167709 10.1016/j.bmcl.2010.11.113 SH-SY5Y 1
19837594 10.1016/j.bmc.2009.09.044 P388 1
19837594 10.1016/j.bmc.2009.09.044 L1210 1
19837594 10.1016/j.bmc.2009.09.044 A549 1
19837593 10.1016/j.bmc.2009.09.039 HUVEC 1
16949281 10.1016/j.bmcl.2006.08.065 Tubulin 1
16949281 10.1016/j.bmcl.2006.08.065 K562 1
15658859 10.1021/jm049444m Tubulin beta-1 chain 1
9871706 10.1016/s0960-894x(98)00162-0 HeLa 1
9871706 10.1016/s0960-894x(98)00162-0 K562 1

Data from ChEMBL 36 via Core Engine