Compound Detail

CHEMBL565612

SOTRASTAURIN

🧪 Phase II

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🧪 Phase II

CN1CCN(c2nc(C3=C(c4c[nH]c5ccccc45)C(=O)NC3=O)c3ccccc3n2)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL565612
Name	SOTRASTAURIN
Phase	Phase II
Structure Type	MOL
InChI Key	OAVGBZOFDPFGPJ-UHFFFAOYSA-N

Known Names

Aeb-071 AEB071 NVP-AEB071 Sotrastaurin Sotrastaurina Sotrastaurine

Targets

129

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

438.5

MW (Da)

2.43

ALogP

HBA

HBD

94.2

PSA (Å²)

0.48

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Year

2008

Extended Properties

Molecular Formula	C25H22N6O2
MW	438.49
Aromatic Rings	4
Heavy Atoms	33
NP-Likeness	-0.57

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Protein kinase C (PKC) inhibitor	INHIBITOR	Protein kinase C (PKC)	✓	✓

Indications

Colitis, Ulcerative Panuveitis Psoriasis Uveitis, Posterior Lymphoma Lymphoma, Large B-Cell, Diffuse Uveal Melanoma

Activity Summary

IC50 63 meas. best 9.66

Ki 49 meas. best 9.2

Kd 16 meas. best 8.3

EC50 1 meas. best 5.01

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Protein kinase C theta type CHEMBL3920	IC50	9.66	8.688	0.2	10
Protein kinase C theta type CHEMBL3920	Ki	9.2	9.2	0.6	1
Protein kinase C beta type CHEMBL3045	IC50	9.19	8.5533	0.6	6
Protein kinase C alpha type CHEMBL299	IC50	9.1	8.5938	0.8	8
Protein kinase C delta type CHEMBL2996	IC50	8.89	8.7225	1.3	4
Serine/threonine-protein kinase pim-2 CHEMBL4523	Ki	8.8	8.8	1.6	1
Serine/threonine-protein kinase D3 CHEMBL2595	IC50	8.68	8.68	2.1	1
Protein kinase C epsilon type CHEMBL3582	IC50	8.49	8.278	3.2	5
Protein kinase C delta type CHEMBL2996	Kd	8.3	8.3	5.0	1
Protein kinase C eta type CHEMBL3616	IC50	8.23	8.215	5.9	4
Misshapen-like kinase 1 CHEMBL5518	Ki	8.1	8.1	7.9	1
Protein kinase C gamma type CHEMBL2938	Ki	7.9	7.9	12.6	1
Protein kinase C alpha type CHEMBL299	Kd	7.89	7.89	13.0	1
Protein kinase C theta type CHEMBL3920	Kd	7.89	7.89	13.0	1
Unchecked CHEMBL612545	Kd	7.8	7.8	16.0	1
Protein kinase C beta type CHEMBL3045	Kd	7.62	7.62	24.0	1
PBMC CHEMBL613107	IC50	7.55	7.55	28.0	1
Calcium/calmodulin-dependent protein kinase type II subunit delta CHEMBL2801	Ki	7.5	7.5	31.6	1
Unchecked CHEMBL612545	IC50	7.47	6.7025	34.0	4
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.43	7.125	37.0	2
TRAF2 and NCK-interacting protein kinase CHEMBL4527	Kd	7.42	7.42	38.0	1
Misshapen-like kinase 1 CHEMBL5518	Kd	7.39	7.39	41.0	1
Serine/threonine-protein kinase pim-1 CHEMBL2147	IC50	7.3	7.3	50.1	1
Jurkat CHEMBL397	IC50	7.27	7.27	54.0	1
Protein kinase C zeta type CHEMBL3438	Ki	7.2	7.2	63.1	1
Serine/threonine-protein kinase PLK1 CHEMBL3024	Ki	7.2	7.2	63.1	1
Protein kinase C gamma type CHEMBL2938	IC50	7.19	7.19	64.0	1
Calcium/calmodulin-dependent protein kinase type II subunit gamma CHEMBL3829	Ki	7.1	7.1	79.4	1
Dual specificity protein kinase CLK2 CHEMBL4225	Kd	6.92	6.92	121.0	1
Ribosomal protein S6 kinase alpha-3 CHEMBL2345	Ki	6.9	6.9	125.9	1
Cyclin-dependent kinase 2 CHEMBL301	Ki	6.9	6.9	125.9	1
STE20-like serine/threonine-protein kinase CHEMBL4202	Ki	6.9	6.9	125.9	1
Serine/threonine-protein kinase 3 CHEMBL4708	Ki	6.9	6.9	125.9	1
Splenocyte CHEMBL612422	IC50	6.89	6.89	128.0	1
Mitogen-activated protein kinase kinase kinase kinase 5 CHEMBL4852	Ki	6.8	6.8	158.5	1
Ribosomal protein S6 kinase beta-1 CHEMBL4501	Ki	6.8	6.8	158.5	1
Mitogen-activated protein kinase kinase kinase kinase 4 CHEMBL6166	Ki	6.8	6.8	158.5	1
Glycogen synthase kinase-3 alpha CHEMBL2850	Ki	6.8	6.8	158.5	1
Macrophage-stimulating protein receptor CHEMBL2689	Ki	6.8	6.8	158.5	1
Serine/threonine-protein kinase pim-1 CHEMBL2147	Ki	6.8	6.8	158.5	1
Glycogen synthase kinase-3 beta CHEMBL262	Ki	6.7	6.7	199.5	1
Protein kinase C beta type CHEMBL3042	IC50	6.63	6.63	234.0	1
Serine/threonine-protein kinase N2 CHEMBL3032	Ki	6.6	6.6	251.2	1
Tyrosine-protein kinase Fer CHEMBL3982	Ki	6.5	6.5	316.2	1
Serine/threonine-protein kinase pim-3 CHEMBL5407	Ki	6.5	6.5	316.2	1
Vascular endothelial growth factor receptor 3 CHEMBL1955	Ki	6.5	6.5	316.2	1
Vascular endothelial growth factor receptor 2 CHEMBL279	Ki	6.4	6.4	398.1	1
Protein kinase C iota type CHEMBL2598	Ki	6.4	6.4	398.1	1
RAC-alpha serine/threonine-protein kinase CHEMBL4282	Ki	6.3	6.3	501.2	1
5'-AMP-activated protein kinase catalytic subunit alpha-1 CHEMBL4045	Ki	6.2	6.2	631.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	1629.0	ng.hr.mL-1	Rattus norvegicus
AUC	2208.0	ng.hr.mL-1	Rattus norvegicus
AUC	1952.0	ng/g.hr	Rattus norvegicus
AUC	20478.0	ng/g.hr	Rattus norvegicus
AUC	30887.0	ng/g.hr	Rattus norvegicus
AUC	12644.0	ng/g.hr	Rattus norvegicus
CL	51.2	mL.min-1.kg-1	Rattus norvegicus
CL	45.0	mL.min-1.kg-1	Mus musculus
CL	51.0	mL.min-1.kg-1	Rattus norvegicus
CL	23.0	mL.min-1.kg-1	Macaca fascicularis
CL	248.0	mL.min-1.g-1	Mus musculus
CL	505.0	mL.min-1.g-1	Rattus norvegicus
CL	433.0	mL.min-1.g-1	Macaca fascicularis
Cmax	1418.5	nM	Rattus norvegicus
F	34.0	%	Rattus norvegicus
F	19.0	%	Mus musculus
F	34.0	%	Rattus norvegicus
F	18.0	%	Macaca fascicularis
Fu	0.011	-	Rattus norvegicus
Fu	0.024	-	Macaca fascicularis
T1/2	3.2	hr	Rattus norvegicus
T1/2	2.5	hr	Mus musculus
T1/2	3.2	hr	Rattus norvegicus
T1/2	4.8	hr	Macaca fascicularis
Tmax	0.5	hr	Rattus norvegicus
Tmax	0.5	hr	Mus musculus
Tmax	0.5	hr	Rattus norvegicus
Tmax	8.0	hr	Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Protein kinase C theta type	IC50	=	0.22	nM	9.66	Inhibition of full length human PKCtheta using 5-FAM-RFARKGSLRQKNV-OH peptide su...	35167283
Protein kinase C theta type	IC50	=	0.3	nM	9.52	Inhibition of PKCtheta (unknown origin) incubated for 15 mins in presence of 33P...	38198520
Protein kinase C theta type	Ki	=	0.631	nM	9.2	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Protein kinase C beta type	IC50	=	0.64	nM	9.19	Inhibition of PKCbeta1 (unknown origin) by IMAP kinase assay	35167283
Protein kinase C theta type	IC50	=	0.7	nM	9.15	Inhibition of PKC theta (unknown origin) in presence of ATP at Km	38307441
Protein kinase C alpha type	IC50	=	0.8	nM	9.1	Inhibition of PKCalpha (unknown origin) incubated for 15 mins in presence of 33P...	38198520
Protein kinase C alpha type	IC50	=	0.95	nM	9.02	Inhibition of PKCalpha (unknown origin)	35167283
Protein kinase C theta type	IC50	=	1.0	nM	9.0	Inhibition of PKCtheta by SPA	19827831
Protein kinase C theta type	IC50	=	1.0	nM	9.0	Inhibition of PKCtheta by scintillation proximity assay	21797275
Protein kinase C theta type	IC50	=	1.0	nM	9.0	Inhibition of PKCtheta (unknown origin) after 60 mins in presence of [gamma33P]A...	28131714
Protein kinase C delta type	IC50	=	1.3	nM	8.89	Inhibition of PKCdelta by SPA	19827831
Protein kinase C delta type	IC50	=	1.3	nM	8.89	Inhibition of PKCdelta by scintillation proximity assay	21797275
Protein kinase C delta type	IC50	=	1.3	nM	8.89	Inhibition of PKCdelta (unknown origin) after 60 mins in presence of [gamma33P]A...	28131714
Serine/threonine-protein kinase pim-2	Ki	=	1.585	nM	8.8	PUBCHEM_BIOASSAY: Navigating the Kinome. (Class of assay: other) Panel member na...	-
Protein kinase C beta type	IC50	=	2.0	nM	8.7	Inhibition of PKCbeta-1 by scintillation proximity assay	21797275
Protein kinase C alpha type	IC50	=	2.0	nM	8.7	Inhibition of PKC alpha (unknown origin) in presence of ATP at Km	38307441
Protein kinase C beta type	IC50	=	2.0	nM	8.7	Inhibition of PKCbeta1 (unknown origin) after 60 mins in presence of [gamma33P]A...	28131714
Protein kinase C beta type	IC50	=	2.0	nM	8.7	Inhibition of PKCbeta1 by SPA	19827831
Protein kinase C alpha type	IC50	=	2.1	nM	8.68	Inhibition of PKCalpha by SPA	19827831
Protein kinase C theta type	IC50	=	2.1	nM	8.68	Inhibition of PKCtheta (unknown origin)	38198520

Literature References

PubMed	DOI	Target Context	# Activities
19827831	10.1021/jm901108b	Rattus norvegicus	10
21797275	10.1021/jm200469u	Mus musculus	8
21797275	10.1021/jm200469u	Cynomolgus monkey	8
21797275	10.1021/jm200469u	Rattus norvegicus	8
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
21797275	10.1021/jm200469u	No relevant target	6
29191878	10.1126/science.aan4368	Unchecked	6
19827831	10.1021/jm901108b	Unchecked	3
38307441	10.1016/j.bmcl.2024.129630	Protein kinase C theta type	3
21797275	10.1021/jm200469u	ADMET	3
-	10.6019/CHEMBL5303304	Fibroblast	3
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	3
35167283	10.1021/acs.jmedchem.1c01031	Protein kinase C beta type	3
25000588	10.1021/jm500669m	Rattus norvegicus	3
28131714	10.1016/j.bmcl.2017.01.038	Protein kinase C theta type	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
35167283	10.1021/acs.jmedchem.1c01031	Protein kinase C alpha type	2
21797275	10.1021/jm200469u	Caco-2	2
21797275	10.1021/jm200469u	Plasma	2
38307441	10.1016/j.bmcl.2024.129630	Protein kinase C alpha type	2

Data from ChEMBL 36 via Core Engine