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Compound Detail

CHEMBL470334

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N#Cc1ccc(COC[C@H]2O[C@@H](n3c(NCc4ccc(Cl)c(Cl)c4)nc4c(N)ncnc43)[C@H](O)[C@@H]2O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL470334
Phase Preclinical
Structure Type MOL
InChI Key ZXGGCBQORXDVTE-UMCMBGNQSA-N
8
Targets
22
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

556.4
MW (Da)
3.04
ALogP
11
HBA
4
HBD
164.4
PSA (Ų)
0.25
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 C25H23Cl2N7O4
MW 556.41
Aromatic Rings 4
Heavy Atoms 38
NP-Likeness -0.49

Activity Summary

EC50 10 meas. best 5.26
Kd 6 meas. best 7.1
IC50 5 meas. best 6.96
Ki 1 meas. best 6.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Endoplasmic reticulum chaperone BiP
CHEMBL1781865
 Kd 7.1 6.9 80.0 2
Transient receptor potential cation channel subfamily M member 7
CHEMBL3714706
 IC50 6.96 6.96 110.0 1
Unchecked
CHEMBL612545
 Ki 6.92 6.92 120.0 1
Unchecked
CHEMBL612545
 Kd 6.69 6.5625 206.0 4
Unchecked
CHEMBL612545
 IC50 6.3 6.3 500.0 2
Endoplasmic reticulum chaperone BiP
CHEMBL1781865
 IC50 6.1 6.1 800.0 1
BaF3
CHEMBL614524
 EC50 5.26 5.185 5500.0 2
BV-173
CHEMBL2366145
 EC50 5.25 5.245 5640.0 2
HEK293
CHEMBL614818
 EC50 5.19 5.15 6460.0 2
K562
CHEMBL385
 EC50 5.15 5.13 7050.0 2
Unchecked
CHEMBL612545
 EC50 5.07 5.065 8500.0 2
Heat shock cognate 71 kDa protein
CHEMBL1275223
 IC50 4.98 4.98 10400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Endoplasmic reticulum chaperone BiP Kd = 80.0 nM 7.1 Binding affinity to histidine-tagged Grp78 by surface plasmon resonance analysis 21526763
Transient receptor potential cation channel subfamily M member 7 IC50 = 110.0 nM 6.96 Inhibition of mouse TRPM7 transfected in HEK293T cells assessed as inhibition of... 38537009
Unchecked Ki = 120.0 nM 6.92 Inhibition of HSP70 by fluorescence polarization assay 21526763
Endoplasmic reticulum chaperone BiP Kd = 200.0 nM 6.7 Binding affinity to Grp78 by isothermal titration calorimetric analysis 21526763
Unchecked Kd = 206.0 nM 6.69 Binding affinity to human HSP70 at 25 degC by surface plasmon resonance assay 25935385
Unchecked Kd = 300.0 nM 6.52 Binding affinity to HSP70 by surface plasmon resonance analysis 21526763
Unchecked Kd = 300.0 nM 6.52 Binding affinity to Hsp70 nucleotide binding domain 20608738
Unchecked Kd = 300.0 nM 6.52 Binding affinity to HSP70 by Biocore direct binding assay 19256508
Unchecked IC50 = 500.0 nM 6.3 Displacement of fluorescein labeled N6-(6-amino)hexyl-ATP-5-FAM from HSP70 by fl... 19256508
Unchecked IC50 = 500.0 nM 6.3 Inhibition of Hsp70 (unknown origin) by ATPase activity 37839344
Endoplasmic reticulum chaperone BiP IC50 = 800.0 nM 6.1 Inhibition of GRP78 (26 to 636 residues) (unknown origin) expressed in Escherich... 31129054
BaF3 EC50 = 5500.0 nM 5.26 Induction of apoptosis in mouse BaF3 cells incubated for 24 hrs by annexin V/PI ... 38011535
BV-173 EC50 = 5640.0 nM 5.25 Induction of apoptosis in human BV-173 cells incubated for 48 hrs by Annexin V-F... 39012838
BV-173 EC50 = 5800.0 nM 5.24 Induction of apoptosis in human BV-173 cells incubated for 24 hrs by annexin V/P... 38011535
HEK293 EC50 = 6460.0 nM 5.19 Induction of apoptosis in HEK293 cells incubated for 48 hrs by Annexin V-FITC st... 39012838
K562 EC50 = 7050.0 nM 5.15 Induction of apoptosis in human K562 cells incubated for 48 hrs by Annexin V-FIT... 39012838
BaF3 EC50 = 7730.0 nM 5.11 Induction of apoptosis in mouse BaF3 cells incubated for 48 hrs by Annexin V-FIT... 39012838
HEK293 EC50 = 7700.0 nM 5.11 Induction of apoptosis in human HEK293 cells incubated for 24 hrs by annexin V/P... 38011535
K562 EC50 = 7800.0 nM 5.11 Induction of apoptosis in human K562 cells incubated for 24 hrs by annexin V/PI ... 38011535
Unchecked EC50 = 8500.0 nM 5.07 Induction of apoptosis in human Imatinib-resistant K562-R3 cells incubated for 2... 38011535

Literature References

PubMed DOI Target Context # Activities
39012838 10.1021/acs.jmedchem.4c00780 Unchecked 5
19256508 10.1021/jm801627a Unchecked 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
38011535 10.1021/acs.jmedchem.3c01783 Unchecked 3
31129054 10.1016/j.bmcl.2019.05.041 Endoplasmic reticulum chaperone BiP 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
31725295 10.1021/acs.jmedchem.9b01709 Heat shock-related 70 kDa protein 2 2
27155465 10.1016/j.ejmech.2016.04.042 Unchecked 2
25935385 10.1016/j.ejmech.2015.04.043 Unchecked 2
21526763 10.1021/jm101625x Unchecked 2
21526763 10.1021/jm101625x Endoplasmic reticulum chaperone BiP 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
21526763 10.1021/jm101625x HCT-116 1
32199134 10.1016/j.ejmech.2020.112228 Endoplasmic reticulum chaperone BiP 1
20608738 10.1021/jm100342z Unchecked 1
- 10.6019/EOS300108 HepG2 1
20608738 10.1021/jm100342z Heat shock cognate 71 kDa protein 1
38011535 10.1021/acs.jmedchem.3c01783 BV-173 1
37839344 10.1016/j.ejmech.2023.115859 Unchecked 1

Data from ChEMBL 36 via Core Engine