Compound Detail

CHEMBL383264

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N[C@H](COc1cncc(-c2ccc3cnccc3c2)c1)Cc1c[nH]c2ccccc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL383264
Phase	Preclinical
Structure Type	MOL
InChI Key	LHQWPYOYDRVMFI-QFIPXVFZSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

394.5

MW (Da)

4.73

ALogP

HBA

HBD

76.8

PSA (Å²)

0.44

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C25H22N4O
MW	394.48
Aromatic Rings	5
Heavy Atoms	30
NP-Likeness	-0.50

Activity Summary

IC50 31 meas. best 8.89

EC50 2 meas. best 6.4

Ki 2 meas. best 8.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
RAC-alpha serine/threonine-protein kinase CHEMBL4282	IC50	8.89	7.4238	1.3	8
RAC-alpha serine/threonine-protein kinase CHEMBL4282	Ki	8.7	8.7	2.0	1
cAMP-dependent protein kinase (PKA) CHEMBL2094138	IC50	8.68	8.68	2.1	2
RAC-beta serine/threonine-protein kinase CHEMBL2431	IC50	8.17	8.17	6.8	2
RAC-gamma serine/threonine-protein kinase CHEMBL4816	IC50	7.46	7.46	35.0	2
Cyclin-dependent kinase 1 CHEMBL308	IC50	7.0	7.0	100.0	2
Protein kinase C gamma type CHEMBL2938	IC50	6.57	6.57	270.0	2
MIA PaCa-2 CHEMBL614725	EC50	6.4	6.4	400.0	1
F5.12 CHEMBL614948	IC50	6.38	6.38	420.0	1
MIA PaCa-2 CHEMBL614725	IC50	6.23	6.23	590.0	3
Mitogen-activated protein kinase 1 CHEMBL4040	IC50	6.04	6.04	910.0	2
RAC-alpha serine/threonine-protein kinase CHEMBL4282	EC50	5.82	5.82	1500.0	1
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	5.7	5.7	2000.0	1
Serine/threonine-protein kinase Chk1 CHEMBL4630	IC50	5.38	5.38	4200.0	1
Serine/threonine-protein kinase Chk1 CHEMBL4630	Ki	5.3	5.3	5011.9	1
Protein kinase C epsilon type CHEMBL3582	IC50	5.21	5.21	6100.0	1
Protein kinase C delta type CHEMBL2996	IC50	5.21	5.21	6100.0	1
Casein kinase II CHEMBL2095191	IC50	4.93	4.93	11800.0	2
Mast/stem cell growth factor receptor Kit CHEMBL1936	IC50	4.58	4.58	26200.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	-	ng.hr.mL-1	Mus musculus
AUC	7600.0	ng.hr.mL-1	Mus musculus
CL	19.5	L/hr	Mus musculus
F	-	%	Mus musculus
F	-	%	Mus musculus
T1/2	0.3	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
RAC-alpha serine/threonine-protein kinase	IC50	=	1.3	nM	8.89	Inhibition of Akt1 at 10 uM ATP	16413780
RAC-alpha serine/threonine-protein kinase	Ki	=	2.0	nM	8.7	Inhibition of Akt1 in presence of 10 uM ATP	16678413
RAC-alpha serine/threonine-protein kinase	IC50	=	2.0	nM	8.7	Inhibition of Akt1 at 5 uM ATP	16603355
RAC-alpha serine/threonine-protein kinase	IC50	=	2.0	nM	8.7	Inhibition of AKT1 in presence of 5 uM ATP	16644221
RAC-alpha serine/threonine-protein kinase	IC50	=	2.0	nM	8.7	Inhibition of Akt	19497644
cAMP-dependent protein kinase (PKA)	IC50	=	2.1	nM	8.68	Inhibition of PKA at 10 uM ATP	16413780
cAMP-dependent protein kinase (PKA)	IC50	=	2.1	nM	8.68	Inhibition of PKA at 5 uM ATP	16603355
RAC-beta serine/threonine-protein kinase	IC50	=	6.8	nM	8.17	Inhibition of Akt2 at 10 uM ATP	16413780
RAC-beta serine/threonine-protein kinase	IC50	=	6.8	nM	8.17	Inhibition of Akt2 at 5 uM ATP	16603355
RAC-gamma serine/threonine-protein kinase	IC50	=	35.0	nM	7.46	Inhibition of Akt3 at 10 uM ATP	16413780
RAC-gamma serine/threonine-protein kinase	IC50	=	35.0	nM	7.46	Inhibition of Akt3 at 5 uM ATP	16603355
Cyclin-dependent kinase 1	IC50	=	100.0	nM	7.0	Inhibition of CDK1 at 10 uM ATP	16413780
Cyclin-dependent kinase 1	IC50	=	100.0	nM	7.0	Inhibition of CDK1 at 5 uM ATP	16603355
Protein kinase C gamma type	IC50	=	270.0	nM	6.57	Inhibition of PKCgamma at 10 uM ATP	16413780
Protein kinase C gamma type	IC50	=	270.0	nM	6.57	Inhibition of PKC gamma at 5 uM ATP	16603355
MIA PaCa-2	EC50	=	400.0	nM	6.4	Antiproliferative activity against human MiaPaCa2 cell line	16678413
RAC-alpha serine/threonine-protein kinase	IC50	=	420.0	nM	6.38	Antiproliferative activity against Akt1 overexpressing murine FL5.12-Akt1 cell	16413780
RAC-alpha serine/threonine-protein kinase	IC50	=	420.0	nM	6.38	Antiproliferative activity against mouse FL5.12 cells overexpressing Akt1 by MTT...	16603355
F5.12	IC50	=	420.0	nM	6.38	Cytotoxicity against F5.12-Akt cells by MTT assay in presence of 5 uM ATP	16644221
MIA PaCa-2	IC50	=	590.0	nM	6.23	Antiproliferative activity against human MiaPaCa-2 cells	16413780

Literature References

PubMed	DOI	Target Context	# Activities
16644221	10.1016/j.bmcl.2006.04.005	Unchecked	9
16603355	10.1016/j.bmcl.2006.03.041	Mus musculus	6
16603355	10.1016/j.bmcl.2006.03.041	RAC-alpha serine/threonine-protein kinase	3
16413780	10.1016/j.bmcl.2005.12.065	RAC-alpha serine/threonine-protein kinase	3
16644221	10.1016/j.bmcl.2006.04.005	RAC-alpha serine/threonine-protein kinase	2
16413780	10.1016/j.bmcl.2005.12.065	Serine/threonine-protein kinase Chk1	1
16603355	10.1016/j.bmcl.2006.03.041	RAC-gamma serine/threonine-protein kinase	1
16603355	10.1016/j.bmcl.2006.03.041	RAC-beta serine/threonine-protein kinase	1
16413780	10.1016/j.bmcl.2005.12.065	Proto-oncogene tyrosine-protein kinase Src	1
16413780	10.1016/j.bmcl.2005.12.065	Mast/stem cell growth factor receptor Kit	1
16413780	10.1016/j.bmcl.2005.12.065	Vascular endothelial growth factor receptor 3	1
16413780	10.1016/j.bmcl.2005.12.065	Vascular endothelial growth factor receptor 2	1
16413780	10.1016/j.bmcl.2005.12.065	Casein kinase II	1
16413780	10.1016/j.bmcl.2005.12.065	MAP kinase-activated protein kinase 2	1
16413780	10.1016/j.bmcl.2005.12.065	Mitogen-activated protein kinase 1	1
19497644	10.1016/j.ejmech.2009.04.050	RAC-alpha serine/threonine-protein kinase	1
16413780	10.1016/j.bmcl.2005.12.065	Protein kinase C delta type	1
16413780	10.1016/j.bmcl.2005.12.065	Protein kinase C gamma type	1
16413780	10.1016/j.bmcl.2005.12.065	cAMP-dependent protein kinase (PKA)	1
16413780	10.1016/j.bmcl.2005.12.065	RAC-gamma serine/threonine-protein kinase	1

Data from ChEMBL 36 via Core Engine