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Compound Detail

CHEMBL4288103

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CN1CCC(c2nc(-c3ccc(F)cc3)c(-c3ccnc(Nc4ccc(N5CCNCC5)cc4)n3)s2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4288103
Phase Preclinical
Structure Type MOL
InChI Key GJHIMWIYQKRLGZ-UHFFFAOYSA-N
4
Targets
8
Activities
2
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

529.7
MW (Da)
5.37
ALogP
8
HBA
2
HBD
69.2
PSA (Ų)
0.35
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H32FN7S
MW 529.69
Aromatic Rings 4
Heavy Atoms 38
NP-Likeness -1.42

Activity Summary

EC50 5 meas. best 7.04
IC50 3 meas. best 9.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
cGMP-dependent protein kinase
CHEMBL2169724
 IC50 9.15 8.925 0.7 2
Plasmodium falciparum
CHEMBL364
 EC50 7.04 6.4425 92.0 4
L929
CHEMBL612267
 EC50 5.29 5.29 5100.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.55 4.55 28200.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.48 mL.min-1.g-1 Mus musculus
CL 0.46 mL.min-1.g-1 Rattus norvegicus
CL 0.57 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
cGMP-dependent protein kinase IC50 = 0.7 nM 9.15 Inhibition of Plasmodium falciparum protein kinase G 30174152
cGMP-dependent protein kinase IC50 = 2.0 nM 8.7 Inhibition of Plasmodium falciparum full length N-terminal His-tagged PKG expres... 31566384
Plasmodium falciparum EC50 = 92.0 nM 7.04 Antimalarial activity against Plasmodium falciparum after 48 hrs by microbeta sc... 30174152
Plasmodium falciparum EC50 = 480.0 nM 6.32 Antiplasmodial activity against asexual form of Plasmodium falciparum NF54 asses... 31566384
Plasmodium falciparum EC50 = 510.0 nM 6.29 Antiplasmodial activity against asexual form of Plasmodium falciparum NF54 asses... 31566384
Plasmodium falciparum EC50 = 750.0 nM 6.12 Antiplasmodial activity against Plasmodium falciparum 3D7A erythrocytic stage as... 31566384
L929 EC50 = 5100.0 nM 5.29 Cytotoxicity against mouse L929 cells assessed as reduction in viability by dual... 31566384
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 28200.0 nM 4.55 Inhibition of human ERG expressed in CHO cells by Q-patch clamp assay 31566384

Literature References

PubMed DOI Target Context # Activities
31566384 10.1021/acs.jmedchem.9b01099 Plasmodium falciparum 3
31566384 10.1021/acs.jmedchem.9b01099 No relevant target 3
30174152 10.1016/j.bmcl.2018.08.028 No relevant target 3
31566384 10.1021/acs.jmedchem.9b01099 ADMET 3
30174152 10.1016/j.bmcl.2018.08.028 ADMET 2
30174152 10.1016/j.bmcl.2018.08.028 cGMP-dependent protein kinase 1
30174152 10.1016/j.bmcl.2018.08.028 Rho-associated protein kinase 2 1
30174152 10.1016/j.bmcl.2018.08.028 Unchecked 1
30174152 10.1016/j.bmcl.2018.08.028 Serine/threonine-protein kinase Sgk1 1
30174152 10.1016/j.bmcl.2018.08.028 RAC-beta serine/threonine-protein kinase 1
30174152 10.1016/j.bmcl.2018.08.028 Mitogen-activated protein kinase 14 1
30174152 10.1016/j.bmcl.2018.08.028 Mitogen-activated protein kinase 9 1
30174152 10.1016/j.bmcl.2018.08.028 Mitogen-activated protein kinase 8 1
30174152 10.1016/j.bmcl.2018.08.028 Mitogen-activated protein kinase 1 1
30174152 10.1016/j.bmcl.2018.08.028 Plasmodium falciparum 1
30174152 10.1016/j.bmcl.2018.08.028 RAC-alpha serine/threonine-protein kinase 1
30174152 10.1016/j.bmcl.2018.08.028 3-phosphoinositide-dependent protein kinase 1 1
30174152 10.1016/j.bmcl.2018.08.028 Ribosomal protein S6 kinase alpha-3 1
30174152 10.1016/j.bmcl.2018.08.028 Ribosomal protein S6 kinase alpha-1 1
30174152 10.1016/j.bmcl.2018.08.028 Dual specificity mitogen-activated protein kinase kinase 1 1

Data from ChEMBL 36 via Core Engine