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Compound Detail

CHEMBL423698

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COc1ccc(/C=C/C(=O)/C=C/c2ccc(OC)c(OC)c2)cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL423698
Phase Preclinical
Structure Type MOL
InChI Key BUWQOPHMYRXMLL-NXZHAISVSA-N
15
Targets
26
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

354.4
MW (Da)
4.02
ALogP
5
HBA
0
HBD
54.0
PSA (Ų)
0.67
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H22O5
MW 354.40
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.22

Activity Summary

IC50 25 meas. best 5.82
EC50 1 meas. best 6.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma brucei
CHEMBL612849
 EC50 6.38 6.38 420.0 1
HCT-116
CHEMBL394
 IC50 5.82 5.82 1500.0 1
MDA-MB-231
CHEMBL400
 IC50 5.8 5.8 1600.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.77 5.74 1690.0 2
K562
CHEMBL385
 IC50 5.74 5.74 1830.0 1
NCI-H460
CHEMBL396
 IC50 5.73 5.73 1860.0 1
MCF7
CHEMBL387
 IC50 5.7 5.2333 2000.0 3
UACC-62
CHEMBL614610
 IC50 5.67 5.67 2120.0 1
HT-29
CHEMBL384
 IC50 5.66 5.635 2170.0 2
LNCaP
CHEMBL612518
 IC50 5.66 5.565 2200.0 2
PC-3
CHEMBL390
 IC50 5.63 5.53 2320.0 4
OVCAR-3
CHEMBL614213
 IC50 5.63 5.63 2320.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.62 5.15 2370.0 4
PANC-1
CHEMBL614139
 IC50 5.47 5.47 3390.0 1
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma brucei EC50 = 420.0 nM 6.38 Antitrypanosomal activity against Trypanosoma brucei Lister 427 assessed as para... 36608774
HCT-116 IC50 = 1500.0 nM 5.82 Antiproliferative activity against human HCT116 cells assessed as cell growth in... 32172081
MDA-MB-231 IC50 = 1600.0 nM 5.8 Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT as... 19249204
Plasmodium falciparum IC50 = 1690.0 nM 5.77 Antiplasmodial activity against blood stage of chloroquine-resistant Plasmodium ... 21493068
K562 IC50 = 1830.0 nM 5.74 Antitumor activity against human K562 cells after 48 hrs by SRB assay 20696583
NCI-H460 IC50 = 1860.0 nM 5.73 Antitumor activity against human NCI-H460 cells after 48 hrs by SRB assay 20696583
Plasmodium falciparum IC50 = 1970.0 nM 5.71 Antiplasmodial activity against blood stage of chloroquine-sensitive Plasmodium ... 21493068
MCF7 IC50 = 2000.0 nM 5.7 Antitumor activity against human MCF7 cells after 48 hrs by SRB assay 20696583
UACC-62 IC50 = 2120.0 nM 5.67 Antitumor activity against human UACC62 cells after 48 hrs by SRB assay 20696583
LNCaP IC50 = 2200.0 nM 5.66 Antiproliferative activity against human LNCAP cells after 72 hrs by MTT assay 19249204
HT-29 IC50 = 2170.0 nM 5.66 Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay 22551677
PC-3 IC50 = 2320.0 nM 5.63 Antitumor activity against human PC3 cells after 48 hrs by SRB assay 20696583
OVCAR-3 IC50 = 2320.0 nM 5.63 Antitumor activity against human OVCAR-3 cells after 48 hrs by SRB assay 20696583
NON-PROTEIN TARGET IC50 = 2370.0 nM 5.62 Antitumor activity against human NCI/ADR cells after 48 hrs by SRB assay 20696583
HT-29 IC50 = 2430.0 nM 5.61 Antitumor activity against human HT-29 cells after 48 hrs by SRB assay 20696583
MCF7 IC50 = 2500.0 nM 5.6 Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay 19249204
PC-3 IC50 = 2900.0 nM 5.54 Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay 19249204
PC-3 IC50 = 2980.0 nM 5.53 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 22551677
LNCaP IC50 = 3400.0 nM 5.47 Cytotoxicity against human LNCaP cell line 16789753
NON-PROTEIN TARGET IC50 = 3360.0 nM 5.47 Antitumor activity against human 786-O cells after 48 hrs by SRB assay 20696583

Literature References

PubMed DOI Target Context # Activities
24275249 10.1016/j.ejmech.2013.10.073 Molecular identity unknown 4
25728027 10.1016/j.ejmech.2015.02.005 No relevant target 4
21493068 10.1016/j.bmcl.2011.03.037 Plasmodium falciparum 3
30108820 10.1039/C6MD00649C Pichia kudriavzevii 3
30108820 10.1039/C6MD00649C Candida albicans 3
30108820 10.1039/C6MD00649C Candida tropicalis 3
25728027 10.1016/j.ejmech.2015.02.005 NON-PROTEIN TARGET 2
20696583 10.1016/j.bmc.2010.07.026 NON-PROTEIN TARGET 2
30108820 10.1039/C6MD00649C HUVEC 2
19249204 10.1016/j.bmcl.2009.01.104 MDA-MB-231 1
32172081 10.1016/j.ejmech.2020.112177 HCT-116 1
20696583 10.1016/j.bmc.2010.07.026 K562 1
20696583 10.1016/j.bmc.2010.07.026 UACC-62 1
20060305 10.1016/j.bmc.2009.12.045 DLD-1 1
20060305 10.1016/j.bmc.2009.12.045 HCT-116 1
19249204 10.1016/j.bmcl.2009.01.104 LNCaP 1
19249204 10.1016/j.bmcl.2009.01.104 PC-3 1
16789753 10.1021/jm051043z LNCaP 1
11831895 10.1021/jm010399h Human immunodeficiency virus type 1 integrase 1
9767632 10.1021/jm9707232 KB 1

Data from ChEMBL 36 via Core Engine