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Compound Detail

CHEMBL112953

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C#CCCCn1c(Cc2cc(OC)c(OC)c(OC)c2Cl)nc2c(N)nc(F)nc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL112953
Phase Preclinical
Structure Type MOL
InChI Key KCIOVTSUEXGUFJ-UHFFFAOYSA-N
7
Targets
17
Activities
2
Assay Types
0
PK Parameters
13
Publications
0
Known Names

Molecular Properties

433.9
MW (Da)
3.23
ALogP
8
HBA
1
HBD
97.3
PSA (Ų)
0.33
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H21ClFN5O3
MW 433.87
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -0.55

Activity Summary

IC50 14 meas. best 6.18
EC50 3 meas. best 6.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Heat shock protein HSP 90-alpha
CHEMBL3880
 EC50 6.77 6.4433 170.0 3
Heat shock protein HSP 90-beta
CHEMBL4303
 IC50 6.18 6.18 660.0 1
MCF7
CHEMBL387
 IC50 5.92 5.81 1200.0 2
Heat shock protein HSP90
CHEMBL2095165
 IC50 5.82 5.2629 1500.0 7
SK-BR-3
CHEMBL613834
 IC50 5.75 5.75 1800.0 1
Unchecked
CHEMBL612545
 IC50 5.7 5.65 2000.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.54 5.54 2900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Heat shock protein HSP 90-alpha EC50 = 170.0 nM 6.77 Effective concentration against heat shock protein HSP90-alpha in SKBr3 cells 15828828
Heat shock protein HSP 90-alpha EC50 = 230.0 nM 6.64 Effective concentration against heat shock protein HSP90-alpha in MDA-MB-468 cel... 15828828
Heat shock protein HSP 90-beta IC50 = 660.0 nM 6.18 Displacement of GM-cy3B from Hsp90 in human SKBR3 cells after 24 hrs by fluoresc... 24548207
Heat shock protein HSP 90-alpha EC50 = 1200.0 nM 5.92 Displacement of cy3B-GM from Hsp90alpha 16797988
MCF7 IC50 = 1200.0 nM 5.92 Antiproliferative activity against human MCF7 cells by MTS assay 17488003
Heat shock protein HSP90 IC50 = 1500.0 nM 5.82 Inhibition of Hsp90 protein as degradation of HER2 kinase in SKBr3 cells 15828828
Heat shock protein HSP90 IC50 = 1700.0 nM 5.77 Inhibition of human recombinant HSP90 in MCF7 cells assessed as Her2 degradation 17488003
SK-BR-3 IC50 = 1800.0 nM 5.75 Inhibitory concentration against SKBr3 cell line 15828828
MCF7 IC50 = 1995.26 nM 5.7 Antiproliferative activity evaluated against MCF-7 cell line 14741278
Unchecked IC50 = 2000.0 nM 5.7 Inhibition of Hsp70 in human SKBR3 cells assessed as HER2 protein degradation by... 24548207
Heat shock protein HSP90 IC50 = 2500.0 nM 5.6 Binding affinity to human recombinant HSP90 in MCF7 cell lysates assessed as inh... 17488003
Unchecked IC50 = 2500.0 nM 5.6 Inhibition of Hsp70 in human SKBR3 cells assessed as RAF1 protein degradation by... 24548207
NON-PROTEIN TARGET IC50 = 2900.0 nM 5.54 Growth inhibition of human SKBR3 cells after 72 hrs by Alamar Blue assay 24548207
Heat shock protein HSP90 IC50 = 6000.0 nM 5.22 Binding affinity to human recombinant HSP90 assessed as inhibition of biotinylat... 17488003
Heat shock protein HSP90 IC50 = 7000.0 nM 5.16 Selectivity for HSP90 in MCF7 cells over HSP90 in NDF cells 17488003
Heat shock protein HSP90 IC50 = 18000.0 nM 4.75 Binding affinity to HSP90 in human NDF cell lysates assessed as inhibition of bi... 17488003
Heat shock protein HSP90 IC50 = 30000.0 nM 4.52 Inhibition of ATP-ase activity in human colon tumor cell line (HCT116) 14698151

Literature References

PubMed DOI Target Context # Activities
17488003 10.1021/jm050752+ Heat shock protein HSP90 5
15828828 10.1021/jm049012b Heat shock protein HSP 90-alpha 2
24548207 10.1021/jm401551n Unchecked 2
14698151 10.1016/j.bmcl.2003.11.011 Heat shock protein HSP90 1
14698151 10.1016/j.bmcl.2003.11.011 HCT-116 1
14741278 10.1016/j.bmcl.2003.11.024 MCF7 1
15828828 10.1021/jm049012b Heat shock protein HSP90 1
15828828 10.1021/jm049012b SK-BR-3 1
16797988 10.1016/j.bmcl.2006.06.025 Heat shock protein HSP 90-alpha 1
17488003 10.1021/jm050752+ MCF7 1
19017562 10.1016/j.bmc.2008.10.087 MCF7 1
24548207 10.1021/jm401551n Heat shock protein HSP 90-beta 1
24548207 10.1021/jm401551n NON-PROTEIN TARGET 1

Data from ChEMBL 36 via Core Engine