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Compound Detail

CHEMBL247473

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COc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(CCN3CCc4cc(OC)c(OC)cc4C3)cc2)cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL247473
Phase Preclinical
Structure Type MOL
InChI Key WKEBQZAUNGERGA-UHFFFAOYSA-N
8
Targets
16
Activities
2
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

595.7
MW (Da)
5.83
ALogP
7
HBA
2
HBD
98.4
PSA (Ų)
0.23
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C35H37N3O6
MW 595.70
Aromatic Rings 4
Heavy Atoms 44
NP-Likeness -0.98

Activity Summary

IC50 15 meas. best 7.54
EC50 1 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
K562/A02
CHEMBL4296448
 IC50 7.54 6.29 29.0 2
K562/A02
CHEMBL4296448
 EC50 7.52 7.52 30.3 1
SW-620
CHEMBL612262
 IC50 7.2 7.2 63.0 1
SW620/AD300
CHEMBL4630776
 IC50 6.65 6.65 223.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 6.48 6.476 331.1 5
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 6.07 5.9267 860.0 3
Unchecked
CHEMBL612545
 IC50 5.9 5.9 1250.0 1
K562
CHEMBL385
 IC50 4.71 4.71 19560.0 1
ADMET
CHEMBL612558
 IC50 4.3 4.3 50100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
K562/A02 IC50 = 29.0 nM 7.54 Reversal of multi-drug resistance in human K562/A02 cells assessed as ADR IC50 36708676
K562/A02 EC50 = 30.3 nM 7.52 Reversal of adriamycin resistance in human K562/A02 cells incubated for 48 hrs 36708676
SW-620 IC50 = 63.0 nM 7.2 Reversal of doxorubicin-induced multidrug resistance in human SW620 cells measur... 38389882
SW620/AD300 IC50 = 223.0 nM 6.65 Reversal of doxorubicin-induced multidrug resistance in human SW620/AD300 cells ... 38389882
ATP-dependent translocase ABCB1 IC50 = 331.13 nM 6.48 Inhibition of P-glycoprotein by Hoechst assay 17890094
ATP-dependent translocase ABCB1 IC50 = 331.13 nM 6.48 Inhibition of human Pgp in A2780 cells after 30 mins by Hoechst 33342 assay 18083034
ATP-dependent translocase ABCB1 IC50 = 331.13 nM 6.48 Inhibition of P-gp in human adriamycin-resistant A2780 cells by Hoechst 33342 as... 18678495
ATP-dependent translocase ABCB1 IC50 = 338.84 nM 6.47 Inhibition of P-glycoprotein expressed in A2780/ADR cells by calcein AM assay 17890094
ATP-dependent translocase ABCB1 IC50 = 338.84 nM 6.47 Inhibition of human Pgp in A2780 cells after 30 mins by calcein AM assay 18083034
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 860.0 nM 6.07 Inhibition of BCRP expressed in MDCK cells by pheophorbide A assay 19932960
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 930.0 nM 6.03 Inhibition of BCRP expressed in MCF7 MX cells by Hoechst 33342 staining 19932960
Unchecked IC50 = 1250.0 nM 5.9 Reversal of P-gp-mediated resistance to adriamycin in human K562/A02 cells asses... 27073052
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 2089.3 nM 5.68 Inhibition of ABCG2 in human mitoxantrone-resistant MCF7 cells by Hoechst 33342 ... 18678495
K562/A02 IC50 = 9080.0 nM 5.04 Cytotoxicity against human K562/A02 cells assessed as inhibition of cell growth ... 36708676
K562 IC50 = 19560.0 nM 4.71 Cytotoxicity against human K562 cells assessed as cell viability after 48 hrs by... 27073052
ADMET IC50 = 50100.0 nM 4.3 Cytotoxicity against human K562/A02 cells assessed as cell viability after 48 hr... 27073052

Literature References

PubMed DOI Target Context # Activities
38389882 10.1039/d3md00612c SW620/AD300 7
36708676 10.1016/j.ejmech.2023.115150 K562/A02 4
28355069 10.1021/acs.jmedchem.6b01787 Unchecked 4
17890094 10.1016/j.bmc.2007.07.024 ATP-dependent translocase ABCB1 3
38389882 10.1039/d3md00612c SW-620 3
18083034 10.1016/j.bmc.2007.11.057 ATP-dependent translocase ABCB1 2
27073052 10.1016/j.bmc.2016.03.065 Unchecked 2
19932960 10.1016/j.bmcl.2009.11.004 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
27073052 10.1016/j.bmc.2016.03.065 K562 1
27073052 10.1016/j.bmc.2016.03.065 ADMET 1
19932960 10.1016/j.bmcl.2009.11.004 Multidrug resistance-associated protein 1 1
28355069 10.1021/acs.jmedchem.6b01787 Rattus norvegicus 1
28355069 10.1021/acs.jmedchem.6b01787 K562 1
28355069 10.1021/acs.jmedchem.6b01787 K562/A02 1
18678495 10.1016/j.bmc.2008.07.034 Broad substrate specificity ATP-binding cassette transporter ABCG2 1
18678495 10.1016/j.bmc.2008.07.034 ATP-dependent translocase ABCB1 1
38389882 10.1039/d3md00612c No relevant target 1
38389882 10.1039/d3md00612c ATP-dependent translocase ABCB1 1

Data from ChEMBL 36 via Core Engine