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Compound Detail

CHEMBL2011288

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COc1ccc2[nH]cc(CCNC(=O)c3cc(=O)c4c(OCc5ccc(Br)cc5)cccc4o3)c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2011288
Phase Preclinical
Structure Type MOL
InChI Key YOURSKBAKQLDQW-UHFFFAOYSA-N
3
Targets
15
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

547.4
MW (Da)
5.60
ALogP
5
HBA
2
HBD
93.6
PSA (Ų)
0.26
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H23BrN2O5
MW 547.41
Aromatic Rings 5
Heavy Atoms 36
NP-Likeness -0.52

Activity Summary

EC50 8 meas. best 7.51
IC50 7 meas. best 6.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 EC50 7.51 7.0129 31.0 7
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 6.96 6.605 110.0 4
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 6.13 5.65 745.0 2
Multidrug resistance-associated protein 1
CHEMBL3004
 IC50 5.44 5.44 3599.0 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 EC50 = 31.0 nM 7.51 Inhibition of ABCG2 (unknown origin) transfected in HEK293 cells assessed as inh... 24611893
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 50.0 nM 7.3 Inhibition of ABCG2-mediated mitoxantrone efflux in mitoxantrone-selected human ... 24304387
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 94.0 nM 7.03 Inhibition of ABCG2 (unknown origin) transfected in HEK293 cells assessed as inh... 24611893
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 110.0 nM 6.96 Inhibition of ABCG2-mediated mitoxantrone efflux in HEK293 cells by flow cytomet... 22165858
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 130.0 nM 6.89 Inhibition of ABCG2 (unknown origin)-mediated mitoxantrone efflux expressed in H... 24304387
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 130.0 nM 6.89 Inhibition of ABCG2 (unknown origin) in HEK293 cells assessed as maximal inhibit... 32653696
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 130.0 nM 6.89 Inhibition of ABCG2 (unknown origin)-mediated mitoxantrone efflux 36628850
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 130.0 nM 6.89 Inhibition of ABCG2 (unknown origin) expressed in HEK293 cells assessed as reduc... 25272055
Broad substrate specificity ATP-binding cassette transporter ABCG2 EC50 = 260.0 nM 6.58 Inhibition of ABCG2 (unknown origin) expressed in HEK293 cells assessed as reduc... 27376492
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 380.0 nM 6.42 Inhibition of human ABCG2 expressed in Sf9 insect cell membranes assessed as inh... 24304387
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 707.0 nM 6.15 Inhibition of ABCG2 in topotecan-cultured human MCF7 cells using Hoechst 33342 a... 32105979
ATP-dependent translocase ABCB1 IC50 = 745.0 nM 6.13 Inhibition of sulfasalazine-stimulated ABCB1 ATPase activity (unknown origin) ex... 32105979
Multidrug resistance-associated protein 1 IC50 = 3599.0 nM 5.44 Inhibition of human ABCC1 transfected in MDCK2-MRP1 cells using calcein-AM as su... 32105979
ATP-dependent translocase ABCB1 IC50 = 6756.0 nM 5.17 Inhibition of ABCB1 in human KB-V1 cells using calcein-AM as substrate measured ... 32105979

Literature References

PubMed DOI Target Context # Activities
24304387 10.1021/jm401649j Broad substrate specificity ATP-binding cassette transporter ABCG2 11
22165858 10.1021/jm201404w HEK293 5
32105979 10.1016/j.ejmech.2020.112133 ATP-dependent translocase ABCB1 5
22165858 10.1021/jm201404w Broad substrate specificity ATP-binding cassette transporter ABCG2 4
24611893 10.1021/jm401879z Broad substrate specificity ATP-binding cassette transporter ABCG2 3
25272055 10.1021/jm500943z Broad substrate specificity ATP-binding cassette transporter ABCG2 2
36628850 10.1016/j.ejmech.2022.115070 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
32653696 10.1016/j.ejmech.2020.112503 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
32105979 10.1016/j.ejmech.2020.112133 Multidrug resistance-associated protein 1 2
32105979 10.1016/j.ejmech.2020.112133 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
27376492 10.1016/j.ejmech.2016.05.053 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
22165858 10.1021/jm201404w Multidrug resistance-associated protein 1 2
22165858 10.1021/jm201404w ATP-dependent translocase ABCB1 2
25272055 10.1021/jm500943z HEK293 1
27376492 10.1016/j.ejmech.2016.05.053 ADMET 1
27376492 10.1016/j.ejmech.2016.05.053 NON-PROTEIN TARGET 1
24304387 10.1021/jm401649j ATP-dependent translocase ABCB1 1
31630055 10.1016/j.ejmech.2019.111772 Broad substrate specificity ATP-binding cassette transporter ABCG2 1
24304387 10.1021/jm401649j Multidrug resistance-associated protein 1 1
22165858 10.1021/jm201404w ADMET 1

Data from ChEMBL 36 via Core Engine