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Compound Detail

CHEMBL178737

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O=C1NC(=O)C(c2cnc3ccccn23)=C1c1cn2c3c(cccc13)CN(C(=O)N1CCOCC1)CC2

Basic Information

ChEMBL ID CHEMBL178737
Phase Preclinical
Structure Type MOL
InChI Key INJUVNWOFHYUIN-UHFFFAOYSA-N
24
Targets
28
Activities
2
Assay Types
2
PK Parameters
19
Publications
0
Known Names

Molecular Properties

496.5
MW (Da)
2.12
ALogP
7
HBA
1
HBD
101.2
PSA (Ų)
0.43
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H24N6O4
MW 496.53
Aromatic Rings 4
Heavy Atoms 37
NP-Likeness -1.11

Activity Summary

Ki 18 meas. best 6.5
IC50 10 meas. best 8.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glycogen synthase kinase-3
CHEMBL2095188
IC50 8.89 8.89 1.3 1
Glycogen synthase kinase-3 beta
CHEMBL262
IC50 8.89 8.74 1.3 4
Dual specificity protein kinase CLK4
CHEMBL4203
Ki 6.5 6.5 316.2 1
Cyclin-dependent kinase 2
CHEMBL301
Ki 6.5 6.5 316.2 1
Serine/threonine-protein kinase pim-1
CHEMBL2147
Ki 6.1 6.1 794.3 1
Dual specificity protein kinase CLK2
CHEMBL4225
Ki 6.1 6.1 794.3 1
Tyrosine-protein kinase Lck
CHEMBL258
Ki 6.0 6.0 1000.0 1
Cyclin-dependent kinase 1
CHEMBL308
Ki 6.0 6.0 1000.0 1
Protein kinase C beta type
CHEMBL3045
IC50 5.96 5.96 1100.0 1
Aurora kinase A
CHEMBL4722
Ki 5.9 5.9 1258.9 1
Serine/threonine-protein kinase N2
CHEMBL3032
Ki 5.8 5.8 1584.9 1
Cyclin-dependent kinase 4
CHEMBL331
IC50 5.77 5.77 1700.0 1
Cyclin-dependent kinase 5
CHEMBL4036
Ki 5.7 5.7 1995.3 1
TGF-beta receptor type-2
CHEMBL4267
IC50 5.7 5.7 2000.0 1
Ribosomal protein S6 kinase alpha-3
CHEMBL2345
Ki 5.6 5.6 2511.9 1
Ephrin type-A receptor 2
CHEMBL2068
Ki 5.5 5.5 3162.3 1
STE20-like serine/threonine-protein kinase
CHEMBL4202
Ki 5.5 5.5 3162.3 1
Mitogen-activated protein kinase kinase kinase kinase 4
CHEMBL6166
Ki 5.5 5.5 3162.3 1
Calcium/calmodulin-dependent protein kinase type II subunit gamma
CHEMBL3829
Ki 5.4 5.4 3981.1 1
Protein kinase C gamma type
CHEMBL2938
Ki 5.3 5.3 5011.9 1
Cyclin-dependent kinase 2
CHEMBL301
IC50 5.28 5.28 5300.0 1
Protein kinase C delta type
CHEMBL2996
Ki 5.2 5.2 6309.6 1
Calcium/calmodulin-dependent protein kinase type II subunit delta
CHEMBL2801
Ki 5.2 5.2 6309.6 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL2292
Ki 5.2 5.2 6309.6 1
Mitogen-activated protein kinase kinase kinase 20
CHEMBL3886
IC50 4.87 4.87 13400.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 38.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 42.0 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glycogen synthase kinase-3 beta IC50 = 1.3 nM 8.89 Inhibition of human Glycogen synthase kinase-3 beta 15267232
Glycogen synthase kinase-3 beta IC50 = 1.3 nM 8.89 Inhibition of GSK3-beta 20218623
Glycogen synthase kinase-3 IC50 = 1.3 nM 8.89 Inhibitory concentration against the Glycogen synthase kinase-3 15686883
Glycogen synthase kinase-3 beta IC50 = 2.6 nM 8.59 Inhibitory concentration to inhibit Ser396 phosphorylation of tau, a natural sub... 15686883
Glycogen synthase kinase-3 beta IC50 = 2.6 nM 8.59 Inhibition of Glycogen synthase kinase-3 beta dependent Tau protein serine-396 p... 15267232
Dual specificity protein kinase CLK4 Ki = 316.23 nM 6.5 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Cyclin-dependent kinase 2 Ki = 316.23 nM 6.5 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Serine/threonine-protein kinase pim-1 Ki = 794.33 nM 6.1 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Dual specificity protein kinase CLK2 Ki = 794.33 nM 6.1 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Tyrosine-protein kinase Lck Ki = 1000.0 nM 6.0 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Cyclin-dependent kinase 1 Ki = 1000.0 nM 6.0 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Protein kinase C beta type IC50 = 1100.0 nM 5.96 Inhibition of human Protein kinase C beta 2 15267232
Aurora kinase A Ki = 1258.93 nM 5.9 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Serine/threonine-protein kinase N2 Ki = 1584.89 nM 5.8 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Cyclin-dependent kinase 4 IC50 = 1700.0 nM 5.77 Inhibition of human Cyclin-dependent kinase 4 15267232
TGF-beta receptor type-2 IC50 = 2000.0 nM 5.7 Inhibition of human TGF-beta type II receptor 15267232
Cyclin-dependent kinase 5 Ki = 1995.26 nM 5.7 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Ribosomal protein S6 kinase alpha-3 Ki = 2511.89 nM 5.6 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Mitogen-activated protein kinase kinase kinase kinase 4 Ki = 3162.28 nM 5.5 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -
Ephrin type-A receptor 2 Ki = 3162.28 nM 5.5 PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3301361 ADMET 4
15686883 10.1016/j.bmcl.2004.12.063 Unchecked 3
20218623 10.1021/jm9018756 Glycogen synthase kinase-3 beta 3
15267232 10.1021/jm049768a Rattus norvegicus 3
- 10.6019/CHEMBL3301361 No relevant target 2
15267232 10.1021/jm049768a Glycogen synthase kinase-3 beta 2
15267232 10.1021/jm049768a CaM kinase II 1
15267232 10.1021/jm049768a Mitogen-activated protein kinase kinase kinase 20 1
15267232 10.1021/jm049768a MAP kinase p38 1
15267232 10.1021/jm049768a cAMP-dependent protein kinase catalytic subunit beta 1
15267232 10.1021/jm049768a Cyclin-dependent kinase 4 1
15267232 10.1021/jm049768a Cyclin-dependent kinase 2 1
15267232 10.1021/jm049768a Protein kinase C beta type 1
15267232 10.1021/jm049768a RAC-alpha serine/threonine-protein kinase 1
15267232 10.1021/jm049768a [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial 1
15267232 10.1021/jm049768a Vascular endothelial growth factor receptor 2 1
15267232 10.1021/jm049768a TGF-beta receptor type-2 1
15686883 10.1016/j.bmcl.2004.12.063 Glycogen synthase kinase-3 beta 1
15686883 10.1016/j.bmcl.2004.12.063 Glycogen synthase kinase-3 1

Data from ChEMBL 36 via Core Engine