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Compound Detail

CHEMBL406837

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COc1cccc(/C=C/C(=O)c2c(O)cc(OC)cc2OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL406837
Phase Preclinical
Structure Type MOL
InChI Key AOXAMOYDMUNFNC-BQYQJAHWSA-N
12
Targets
14
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

314.3
MW (Da)
3.31
ALogP
5
HBA
1
HBD
65.0
PSA (Ų)
0.65
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 C18H18O5
MW 314.34
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.46

Activity Summary

IC50 14 meas. best 6.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 6.58 6.58 260.0 1
RAW264.7
CHEMBL612557
 IC50 5.62 5.045 2400.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.51 5.51 3100.0 1
HCT-116
CHEMBL394
 IC50 5.51 5.31 3100.0 2
PC-3
CHEMBL390
 IC50 5.14 5.14 7300.0 1
RL
CHEMBL2366175
 IC50 5.05 5.05 9000.0 1
MCF7
CHEMBL387
 IC50 4.99 4.99 10300.0 1
HaCaT
CHEMBL614392
 IC50 4.98 4.98 10400.0 1
Caco-2
CHEMBL614058
 IC50 4.95 4.95 11200.0 1
MDA-MB-231
CHEMBL400
 IC50 4.88 4.88 13200.0 1
NCI-H727
CHEMBL1075545
 IC50 4.83 4.83 14800.0 1
Huh-7
CHEMBL614039
 IC50 4.82 4.82 15000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 260.0 nM 6.58 Inhibition of ABCG2-mediated mitoxantrone efflux expressed in HEK293 cells after... 22449016
RAW264.7 IC50 = 2400.0 nM 5.62 Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells measur... 32208222
NON-PROTEIN TARGET IC50 = 3100.0 nM 5.51 Antimelanogenic activity in mouse B16F10 cells assessed as inhibition of melanin... 25597012
HCT-116 IC50 = 3100.0 nM 5.51 Antiproliferative activity against human HCT116 cells after 48 hrs by SRB assay 30041135
PC-3 IC50 = 7300.0 nM 5.14 Cytotoxicity against human PC3 cells assessed as cell viability after 48 hrs by ... 28214231
HCT-116 IC50 = 7700.0 nM 5.11 Cytotoxicity against human HCT116 cells assessed as cell viability after 48 hrs ... 28214231
RL IC50 = 9000.0 nM 5.05 Cytotoxicity against human RL assessed as cell viability after 48 hrs by Hoechst... 28214231
MCF7 IC50 = 10300.0 nM 4.99 Cytotoxicity against human MCF7 assessed as cell viability after 48 hrs by Hoech... 28214231
HaCaT IC50 = 10400.0 nM 4.98 Cytotoxicity against human HaCaT cells assessed as cell viability after 48 hrs b... 28214231
Caco-2 IC50 = 11200.0 nM 4.95 Cytotoxicity against human Caco2 cells assessed as cell viability after 48 hrs b... 28214231
MDA-MB-231 IC50 = 13200.0 nM 4.88 Cytotoxicity against human MDA-MB-231 cells assessed as cell viability after 48 ... 28214231
NCI-H727 IC50 = 14800.0 nM 4.83 Cytotoxicity against human NCI-H727 cells assessed as cell viability after 48 hr... 28214231
Huh-7 IC50 = 15000.0 nM 4.82 Cytotoxicity against human HuH7 cells assessed as cell viability after 48 hrs by... 28214231
RAW264.7 IC50 = 34000.0 nM 4.47 Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viabilit... 32208222

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 Huh-7 7
28214231 10.1016/j.bmc.2017.01.049 Caco-2 7
28214231 10.1016/j.bmc.2017.01.049 MCF7 5
32208222 10.1016/j.ejmech.2020.112216 RAW264.7 3
22449016 10.1021/jm2016528 Broad substrate specificity ATP-binding cassette transporter ABCG2 3
22449016 10.1021/jm2016528 HEK293 2
28214231 10.1016/j.bmc.2017.01.049 Fibroblast 2
25597012 10.1016/j.bmcl.2014.12.082 NON-PROTEIN TARGET 1
25597012 10.1016/j.bmcl.2014.12.082 Tyrosinase 1
22449016 10.1021/jm2016528 ADMET 1
22449016 10.1021/jm2016528 Multidrug resistance-associated protein 1 1
28214231 10.1016/j.bmc.2017.01.049 RL 1
22449016 10.1021/jm2016528 ATP-dependent translocase ABCB1 1
30041135 10.1016/j.ejmech.2018.07.037 HCT-116 1

Data from ChEMBL 36 via Core Engine