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Compound Detail

CHEMBL227779

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COc1ccc(/C=C/C(=O)c2cc(OC)c(OC)c(OC)c2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL227779
Phase Preclinical
Structure Type MOL
InChI Key IHAWCLXPXUOJEO-JXMROGBWSA-N
16
Targets
22
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

328.4
MW (Da)
3.62
ALogP
5
HBA
0
HBD
54.0
PSA (Ų)
0.57
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H20O5
MW 328.36
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 0.09

Activity Summary

IC50 22 meas. best 6.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
K562
CHEMBL385
 IC50 6.52 6.52 300.0 1
MCF7
CHEMBL387
 IC50 6.15 6.15 710.0 1
HeLa
CHEMBL399
 IC50 5.89 5.89 1300.0 1
MOLT-4
CHEMBL614177
 IC50 5.85 5.85 1400.0 1
CCRF-CEM
CHEMBL382
 IC50 5.82 5.82 1500.0 1
L1210
CHEMBL386
 IC50 5.55 4.935 2800.0 2
MDA-MB-231
CHEMBL400
 IC50 5.19 5.19 6500.0 1
HT-29
CHEMBL384
 IC50 5.13 5.13 7400.0 2
Peritoneal macrophage cell
CHEMBL613703
 IC50 5.12 5.12 7600.0 1
PC-3
CHEMBL390
 IC50 5.11 5.11 7800.0 2
FM3A
CHEMBL614297
 IC50 5.08 5.08 8400.0 1
HCT-116
CHEMBL394
 IC50 4.97 4.97 10700.0 2
DU-145
CHEMBL613508
 IC50 4.86 4.86 13800.0 2
Unchecked
CHEMBL612545
 IC50 4.71 4.71 19300.0 1
COLO 205
CHEMBL614561
 IC50 4.33 4.33 46400.0 1
HepG2
CHEMBL395
 IC50 4.3 4.3 49500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
K562 IC50 = 300.0 nM 6.52 Antiproliferative activity against human K562 cells after 5 days by MTT assay 19837593
MCF7 IC50 = 710.0 nM 6.15 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability af... 26690274
HeLa IC50 = 1300.0 nM 5.89 Antiproliferative activity against human HeLa cells after 2 days 18440234
MOLT-4 IC50 = 1400.0 nM 5.85 Antiproliferative activity against human MOLT4 cells after 2 days 18440234
CCRF-CEM IC50 = 1500.0 nM 5.82 Antiproliferative activity against human CEM cells after 2 days 18440234
L1210 IC50 = 2800.0 nM 5.55 Antiproliferative activity against mouse L1210 cells after 2 days 18440234
MDA-MB-231 IC50 = 6500.0 nM 5.19 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 26690274
HT-29 IC50 = 7400.0 nM 5.13 Antiproliferative activity against human HT-29 cells after 48 hrs by MTT assay 28838697
HT-29 IC50 = 7440.0 nM 5.13 Antiproliferative activity against human HT29 cells assessed as reduction in cel... 34116328
Peritoneal macrophage cell IC50 = 7600.0 nM 5.12 Inhibition of nitric oxide production in LPS/IFN-gamma-stimulated BALB/c mouse p... 19875299
PC-3 IC50 = 7800.0 nM 5.11 Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay 28838697
PC-3 IC50 = 7800.0 nM 5.11 Antiproliferative activity against human PC3 cells assessed as reduction in cell... 34116328
FM3A IC50 = 8400.0 nM 5.08 Antiproliferative activity against mouse FM3A cells after 2 days 18440234
HCT-116 IC50 = 10700.0 nM 4.97 Antiproliferative activity against human HCT116 cells after 48 hrs by MTT assay 28838697
HCT-116 IC50 = 10740.0 nM 4.97 Antiproliferative activity against human HCT116 cells assessed as reduction in c... 34116328
DU-145 IC50 = 13800.0 nM 4.86 Antiproliferative activity against human DU145 cells after 48 hrs by MTT assay 28838697
DU-145 IC50 = 13820.0 nM 4.86 Antiproliferative activity against human DU145 cells assessed as reduction in ce... 34116328
Unchecked IC50 = 19300.0 nM 4.71 Inhibition of TNFalpha induced NF-kappaB activation in human A549 cells by lucif... 19883086
COLO 205 IC50 = 46400.0 nM 4.33 Growth inhibition of human COLO205 cells after 48 hrs by MTT assay 19875299
L1210 IC50 = 48000.0 nM 4.32 Cytotoxicity against mouse L1210 cells after 24 hrs by MTT assay 23524161

Literature References

PubMed DOI Target Context # Activities
20705463 10.1016/j.bmcl.2010.07.094 Helicobacter pylori 16
17007965 10.1016/j.ejmech.2006.08.012 Candida albicans 3
18584918 10.1016/j.ejmech.2008.05.010 Staphylococcus aureus 2
34116328 10.1016/j.ejmech.2021.113586 HCT-116 1
26690274 10.1021/acs.jnatprod.5b00774 MCF7 1
23524161 10.1016/j.ejmech.2013.02.037 L1210 1
20705463 10.1016/j.bmcl.2010.07.094 AGS 1
20167484 10.1016/j.bmcl.2010.01.113 Angiotensin-converting enzyme 1
19875299 10.1016/j.bmc.2009.10.022 HepG2 1
19875299 10.1016/j.bmc.2009.10.022 COLO 205 1
19875299 10.1016/j.bmc.2009.10.022 Peritoneal macrophage cell 1
19837593 10.1016/j.bmc.2009.09.039 K562 1
19883086 10.1021/jm901278z A549 1
19883086 10.1021/jm901278z NCI-H2009 1
19883086 10.1021/jm901278z Unchecked 1
18440234 10.1016/j.bmc.2008.04.026 HeLa 1
18440234 10.1016/j.bmc.2008.04.026 CCRF-CEM 1
18440234 10.1016/j.bmc.2008.04.026 MOLT-4 1
18440234 10.1016/j.bmc.2008.04.026 FM3A 1
18440234 10.1016/j.bmc.2008.04.026 L1210 1

Data from ChEMBL 36 via Core Engine