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Compound Detail

CHEMBL489058

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CCN1CCN(CC/C=C/c2ccc3c(Nc4ccc(Sc5nccn5C)c(Cl)c4)c(C#N)cnc3c2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL489058
Phase Preclinical
Structure Type MOL
InChI Key OYAMULIHRWEUAR-GQCTYLIASA-N
17
Targets
19
Activities
1
Assay Types
17
PK Parameters
20
Publications
0
Known Names

Molecular Properties

558.1
MW (Da)
6.43
ALogP
8
HBA
1
HBD
73.0
PSA (Ų)
0.25
QED
2
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H32ClN7S
MW 558.15
Aromatic Rings 4
Heavy Atoms 39
NP-Likeness -1.46

Activity Summary

IC50 19 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Epidermal growth factor receptor
CHEMBL203
 IC50 8.0 8.0 10.0 1
Dual specificity mitogen-activated protein kinase kinase 1
CHEMBL3587
 IC50 7.92 7.285 12.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.6 7.6 25.0 1
A-375
CHEMBL613859
 IC50 7.58 7.58 26.0 1
Unchecked
CHEMBL612545
 IC50 7.5 7.08 32.0 2
LoVo
CHEMBL614721
 IC50 7.47 7.47 34.0 1
BXPC-3
CHEMBL614530
 IC50 7.32 7.32 48.0 1
NCI-H358
CHEMBL614135
 IC50 7.3 7.3 50.0 1
Proto-oncogene tyrosine-protein kinase Src
CHEMBL267
 IC50 7.26 7.26 55.0 1
Tyrosine-protein kinase Lyn
CHEMBL3905
 IC50 7.24 7.24 58.0 1
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 6.0 6.0 1000.0 1
Caco-2
CHEMBL614058
 IC50 5.85 5.85 1400.0 1
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial
CHEMBL4766
 IC50 5.51 5.51 3100.0 1
Serine/threonine-protein kinase B-raf
CHEMBL5145
 IC50 5.06 5.06 8800.0 1
Inhibitor of nuclear factor kappa-B kinase subunit beta
CHEMBL1991
 IC50 5.04 5.04 9170.0 1
Ribosomal protein S6 kinase beta-1
CHEMBL4501
 IC50 4.7 4.7 20000.0 1
Protein kinase C theta type
CHEMBL3920
 IC50 4.56 4.56 27400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2170.0 ng.hr.mL-1 Mus musculus
AUC 988.0 ng.hr.mL-1 Rattus norvegicus
AUC 204.0 ng.hr.mL-1 Rattus norvegicus
CL 66.0 mL.min-1.kg-1 Mus musculus
CL 35.7 mL.min-1.kg-1 Rattus norvegicus
CL 70.3 mL.min-1.kg-1 Rattus norvegicus
Cmax 913.73 nM Mus musculus
Cmax 533.91 nM Rattus norvegicus
Cmax 109.29 nM Rattus norvegicus
F 17.0 % Mus musculus
F 23.0 % Rattus norvegicus
F 13.0 % Rattus norvegicus
T1/2 0.9 hr Mus musculus
T1/2 2.5 hr Rattus norvegicus
T1/2 1.8 hr Rattus norvegicus
T1/2 0.275 hr Rattus norvegicus
T1/2 0.35 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Epidermal growth factor receptor IC50 = 10.0 nM 8.0 Inhibition of EGFR in presence of 100 uM ATP 18815050
Dual specificity mitogen-activated protein kinase kinase 1 IC50 = 12.0 nM 7.92 Inhibition of MEK1 by raf/MEK1/MAPK coupled assay 18815050
NON-PROTEIN TARGET IC50 = 25.0 nM 7.6 Antiproliferative activity against human WM266-4 cells by SRB assay 18815050
A-375 IC50 = 26.0 nM 7.58 Antiproliferative activity against human A375 cells by SRB assay 18815050
Unchecked IC50 = 32.0 nM 7.5 Inhibition of IR in presence of 10 uM ATP 18815050
LoVo IC50 = 34.0 nM 7.47 Antiproliferative activity against human LoVo cells by SRB assay 18815050
BXPC-3 IC50 = 48.0 nM 7.32 Antiproliferative activity against human BxPC3 cells by SRB assay 18815050
NCI-H358 IC50 = 50.0 nM 7.3 Antiproliferative activity against human H358 cells by SRB assay 18815050
Proto-oncogene tyrosine-protein kinase Src IC50 = 55.0 nM 7.26 Inhibition of Src in presence of 100 uM ATP 18815050
Tyrosine-protein kinase Lyn IC50 = 58.0 nM 7.24 Inhibition of Lyn in presence of 20 uM ATP 18815050
Unchecked IC50 = 220.0 nM 6.66 Inhibition of IGFR in presence of 100 uM ATP 18815050
Dual specificity mitogen-activated protein kinase kinase 1 IC50 = 225.0 nM 6.65 Inhibition of MEK1-mediated ERK phosphorylation in human WM266-4 cells after 2.5... 18815050
Vascular endothelial growth factor receptor 2 IC50 = 1000.0 nM 6.0 Inhibition of KDR in presence of 1 uM ATP 18815050
Caco-2 IC50 = 1400.0 nM 5.85 Antiproliferative activity against human Caco-2 cells by SRB assay 18815050
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial IC50 = 3100.0 nM 5.51 Inhibition of PDK1 in presence of 100 uM ATP 18815050
Serine/threonine-protein kinase B-raf IC50 = 8800.0 nM 5.06 Inhibition of B-raf in presence of 100 uM ATP 18815050
Inhibitor of nuclear factor kappa-B kinase subunit beta IC50 = 9170.0 nM 5.04 Inhibition of IKK-beta in presence of 2 uM ATP 18815050
Ribosomal protein S6 kinase beta-1 IC50 = 20000.0 nM 4.7 Inhibition of P70S6 in presence of 2 uM ATP 18815050
Protein kinase C theta type IC50 = 27400.0 nM 4.56 Inhibition of PKCtheta in presence of 6 uM ATP 18815050

Literature References

PubMed DOI Target Context # Activities
18815050 10.1016/j.bmc.2008.09.009 Rattus norvegicus 12
18815050 10.1016/j.bmc.2008.09.009 Mus musculus 9
18815050 10.1016/j.bmc.2008.09.009 Dual specificity mitogen-activated protein kinase kinase 1 8
18815050 10.1016/j.bmc.2008.09.009 Unchecked 6
18815050 10.1016/j.bmc.2008.09.009 NCI-H358 3
18815050 10.1016/j.bmc.2008.09.009 Proto-oncogene tyrosine-protein kinase Src 2
18815050 10.1016/j.bmc.2008.09.009 ADMET 2
18815050 10.1016/j.bmc.2008.09.009 Inhibitor of nuclear factor kappa-B kinase subunit beta 1
18815050 10.1016/j.bmc.2008.09.009 No relevant target 1
18815050 10.1016/j.bmc.2008.09.009 Serine/threonine-protein kinase mTOR 1
18815050 10.1016/j.bmc.2008.09.009 RAC-alpha serine/threonine-protein kinase 1
18815050 10.1016/j.bmc.2008.09.009 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 1
18815050 10.1016/j.bmc.2008.09.009 Protein kinase C theta type 1
18815050 10.1016/j.bmc.2008.09.009 Ribosomal protein S6 kinase beta-1 1
18815050 10.1016/j.bmc.2008.09.009 Serine/threonine-protein kinase B-raf 1
18815050 10.1016/j.bmc.2008.09.009 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial 1
18815050 10.1016/j.bmc.2008.09.009 Vascular endothelial growth factor receptor 2 1
18815050 10.1016/j.bmc.2008.09.009 Tyrosine-protein kinase Lyn 1
18815050 10.1016/j.bmc.2008.09.009 Epidermal growth factor receptor 1
18815050 10.1016/j.bmc.2008.09.009 BXPC-3 1

Data from ChEMBL 36 via Core Engine