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Compound Detail

CHEMBL365159

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C#CCCCn1c(Sc2cc3c(cc2Br)OCO3)nc2c(N)ncnc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL365159
Phase Preclinical
Structure Type MOL
InChI Key VNEZLWWMNFSDNW-UHFFFAOYSA-N
8
Targets
24
Activities
2
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

432.3
MW (Da)
3.46
ALogP
8
HBA
1
HBD
88.1
PSA (Ų)
0.49
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H14BrN5O2S
MW 432.30
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -0.87

Activity Summary

IC50 14 meas. best 6.7
EC50 10 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Heat shock protein HSP 90-alpha
CHEMBL3880
 EC50 7.7 5.9867 20.0 6
Heat shock protein HSP 90-alpha
CHEMBL4197
 EC50 7.52 7.52 30.0 1
Heat shock protein HSP 90-beta
CHEMBL4303
 EC50 7.52 7.31 30.0 3
SK-BR-3
CHEMBL613834
 IC50 6.7 6.6 200.0 4
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 IC50 6.52 6.48 300.0 2
Heat shock protein HSP90
CHEMBL2095165
 IC50 6.52 6.43 300.0 2
Heat shock protein HSP 90-alpha
CHEMBL3880
 IC50 6.52 6.52 300.0 1
Heat shock protein HSP 90-beta
CHEMBL4303
 IC50 6.52 6.48 300.0 2
MDA-MB-468
CHEMBL614335
 IC50 6.28 6.265 530.0 2
RPTEC
CHEMBL614883
 IC50 5.39 5.39 4100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Heat shock protein HSP 90-alpha EC50 = 20.0 nM 7.7 Effective concentration against heat shock protein HSP90-alpha in SKBr3 cells 15828828
Heat shock protein HSP 90-alpha EC50 = 30.0 nM 7.52 Displacement of 5 nM GM-BODIPY from mouse heat shock protein HSP90-alpha 15828828
Heat shock protein HSP 90-beta EC50 = 30.0 nM 7.52 Inhibition of Hsp90 19017562
Heat shock protein HSP 90-alpha EC50 = 30.0 nM 7.52 biochemical assay: The biochemical assay tests competitive binding of compounds ... -
Heat shock protein HSP 90-beta EC50 = 50.4 nM 7.3 Inhibitory activity against Hsp90 in human breast cancer SKBr3 cell line 16392823
Heat shock protein HSP 90-alpha EC50 = 50.8 nM 7.29 biochemical assay: The biochemical assay tests competitive binding of compounds ... -
Heat shock protein HSP 90-beta EC50 = 77.1 nM 7.11 Inhibitory activity against Hsp90 in human breast cancer MDA-MB-468 cell line 16392823
SK-BR-3 IC50 = 200.0 nM 6.7 Inhibitory concentration against SKBr3 cell line 15828828
SK-BR-3 IC50 = 200.0 nM 6.7 Cytotoxicity against human SKBR3 cells 19017562
Heat shock protein HSP90 IC50 = 300.0 nM 6.52 Inhibition of Hsp90 protein as degradation of HER2 kinase in SKBr3 cells 15828828
Receptor tyrosine-protein kinase erbB-2 IC50 = 300.0 nM 6.52 biochemical assay: The biochemical assay tests competitive binding of compounds ... -
Heat shock protein HSP 90-alpha IC50 = 300.0 nM 6.52 Displacement of biotin-labeled geldanamycin from N-terminal His-tagged human rec... 20609590
Heat shock protein HSP 90-beta IC50 = 300.0 nM 6.52 Inhibition of Hsp90 in human SKBR3 cells assessed as Her2 degradation 19017562
SK-BR-3 IC50 = 300.0 nM 6.52 Growth inhibition in human breast cancer SKBr3 cell line using SRB 16392823
SK-BR-3 IC50 = 330.0 nM 6.48 Cytotoxicity against human SKBR3 cells after 72 hrs by crystal violet assay 20609590
Heat shock protein HSP 90-beta IC50 = 365.0 nM 6.44 Inhibition of Her2 degradation in human breast cancer SKBr3 cell line 16392823
Receptor tyrosine-protein kinase erbB-2 IC50 = 365.0 nM 6.44 biochemical assay: The biochemical assay tests competitive binding of compounds ... -
Heat shock protein HSP90 IC50 = 460.0 nM 6.34 Inhibition of Hsp90 in human SKBR3 cells assessed as Her2 degradation after 24 h... 20609590
MDA-MB-468 IC50 = 530.0 nM 6.28 Antimitotic activity in human breast cancer MDA-MB-468 cell line 16392823
MDA-MB-468 IC50 = 560.0 nM 6.25 Growth inhibition in human breast cancer MDA-MB-468 cell line using SRB 16392823

Literature References

PubMed DOI Target Context # Activities
17603540 10.1038/nchembio.2007.10 Heat shock protein HSP 90-beta 29
15828828 10.1021/jm049012b Heat shock protein HSP 90-alpha 8
16392823 10.1021/jm0508078 Heat shock protein HSP 90-beta 3
15828828 10.1021/jm049012b RPTEC 2
16392823 10.1021/jm0508078 MDA-MB-468 2
19017562 10.1016/j.bmc.2008.10.087 Heat shock protein HSP 90-beta 2
15828828 10.1021/jm049012b Heat shock protein HSP90 1
15828828 10.1021/jm049012b SK-BR-3 1
16392823 10.1021/jm0508078 SK-BR-3 1
19017562 10.1016/j.bmc.2008.10.087 SK-BR-3 1
20055425 10.1021/jm9004708 Heat shock protein HSP 90-beta 1
20609590 10.1016/j.bmc.2010.05.075 Heat shock protein HSP 90-alpha 1
20609590 10.1016/j.bmc.2010.05.075 Heat shock protein HSP90 1
20609590 10.1016/j.bmc.2010.05.075 SK-BR-3 1

Data from ChEMBL 36 via Core Engine