Compound Detail

CHEMBL4556790

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Cl.Cn1nccc1-c1ccc(C(=O)N[C@@H]2CNCC[C@H]2c2ccc(F)c(F)c2)c(F)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4556790
Phase	Preclinical
Structure Type	MOL
InChI Key	WHVFOLXIIVBJTJ-ICCPGPOKSA-N
Parent Compound	CHEMBL4595425
Active Moiety	CHEMBL4595425

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

414.4

MW (Da)

3.38

ALogP

HBA

HBD

59.0

PSA (Å²)

0.69

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C22H22ClF3N4O
MW	450.89
Aromatic Rings	3
Heavy Atoms	30
NP-Likeness	-1.37

Activity Summary

IC50 33 meas. best 8.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
RAC-alpha serine/threonine-protein kinase CHEMBL4282	IC50	8.4	8.4	4.0	1
Unchecked CHEMBL612545	IC50	7.96	6.2467	11.0	3
RAC-gamma serine/threonine-protein kinase CHEMBL4816	IC50	7.55	7.55	28.0	1
RAC-beta serine/threonine-protein kinase CHEMBL2431	IC50	7.01	7.01	97.5	1
Ribosomal protein S6 kinase beta-1 CHEMBL4501	IC50	6.64	6.64	229.0	1
Rho-associated protein kinase 1 CHEMBL3231	IC50	6.45	6.45	354.0	1
LNCaP CHEMBL612518	IC50	6.21	6.21	610.0	1
Protein kinase C theta type CHEMBL3920	IC50	6.2	6.2	629.0	1
HGC-27 CHEMBL1075463	IC50	6.17	6.17	680.0	1
Ribosomal protein S6 kinase alpha-1 CHEMBL2553	IC50	6.12	6.12	756.0	1
Serine/threonine-protein kinase Sgk1 CHEMBL2343	IC50	6.0	6.0	1009.0	1
786-0 CHEMBL613102	IC50	5.6	5.335	2500.0	2
OVCAR-8 CHEMBL612555	IC50	5.45	5.45	3520.0	1
HepG2 CHEMBL395	IC50	5.44	5.44	3600.0	1
SK-OV-3 CHEMBL614925	IC50	5.33	5.33	4710.0	1
L02 CHEMBL4296457	IC50	5.27	5.27	5400.0	1
A549 CHEMBL392	IC50	5.18	5.18	6560.0	1
U-251 CHEMBL615022	IC50	5.18	5.18	6530.0	1
KHOS/NP CHEMBL612598	IC50	5.13	4.98	7470.0	2
NCI-H1975 CHEMBL614348	IC50	5.12	5.12	7560.0	1
769-P CHEMBL1075385	IC50	5.11	5.11	7760.0	1
PC-3 CHEMBL390	IC50	5.06	5.06	8740.0	1
U-87 MG CHEMBL614247	IC50	5.03	5.03	9260.0	1
OS-RC-2 CHEMBL2366188	IC50	5.0	5.0	9900.0	1
HaCaT CHEMBL614392	IC50	4.82	4.82	15170.0	1
MDA-MB-231 CHEMBL400	IC50	4.79	4.79	16370.0	1
SMMC-7721 CHEMBL613831	IC50	4.7	4.7	19760.0	1
HT-29 CHEMBL384	IC50	4.69	4.69	20290.0	1
Bel-7402 CHEMBL614279	IC50	4.58	4.58	26620.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	2280.84	ng.hr.mL-1	Rattus norvegicus
AUC	459.29	ng.hr.mL-1	Rattus norvegicus
AUC	33283.69	ng.hr.mL-1	Canis lupus familiaris
AUC	2820.64	ng.hr.mL-1	Rattus norvegicus
AUC	532.87	ng.hr.mL-1	Rattus norvegicus
AUC	36303.59	ng.hr.mL-1	Canis lupus familiaris
CL	1.4	mL.min-1.g-1	Homo sapiens
CL	13.6	mL.min-1.g-1	Macaca mulatta
CL	4.1	mL.min-1.g-1	Canis lupus familiaris
CL	20.0	mL.min-1.g-1	Rattus norvegicus
CL	3.4	mL.min-1.g-1	Mus musculus
Cmax	413.1	nM	Rattus norvegicus
Cmax	500.69	nM	Rattus norvegicus
Cmax	2185.17	nM	Canis lupus familiaris
F	66.2	%	Rattus norvegicus
T1/2	16.21	hr	Homo sapiens
T1/2	1.697	hr	Macaca mulatta
T1/2	5.603	hr	Canis lupus familiaris
T1/2	1.157	hr	Rattus norvegicus
T1/2	6.728	hr	Mus musculus
T1/2	8.68	hr	Rattus norvegicus
T1/2	6.24	hr	Rattus norvegicus
T1/2	16.7	hr	Canis lupus familiaris
Tmax	1.67	hr	Rattus norvegicus
Tmax	0.11	hr	Rattus norvegicus
Tmax	8.67	hr	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
RAC-alpha serine/threonine-protein kinase	IC50	=	4.0	nM	8.4	Inhibition of N-terminal GST-tagged human AKT1 (104 to 408 residues) expressed i...	34375113
Unchecked	IC50	=	11.0	nM	7.96	Inhibition of PKA (unknown origin)	34375113
RAC-gamma serine/threonine-protein kinase	IC50	=	28.0	nM	7.55	Inhibition of AKT3 (unknown origin)	34375113
RAC-beta serine/threonine-protein kinase	IC50	=	97.5	nM	7.01	Inhibition of N-terminal GST-tagged human AKT2 (120 to 481 residues) expressed i...	34375113
Ribosomal protein S6 kinase beta-1	IC50	=	229.0	nM	6.64	Inhibition of P70S6K (unknown origin)	34375113
Rho-associated protein kinase 1	IC50	=	354.0	nM	6.45	Inhibition of ROCK1 (unknown origin)	34375113
LNCaP	IC50	=	610.0	nM	6.21	Antiproliferative activity against human LNCaP cells assessed as inhibition of c...	34375113
Protein kinase C theta type	IC50	=	629.0	nM	6.2	Inhibition of PKCtheta (unknown origin)	34375113
HGC-27	IC50	=	680.0	nM	6.17	Antiproliferative activity against human HGC-27 cells assessed as inhibition of ...	34375113
Ribosomal protein S6 kinase alpha-1	IC50	=	756.0	nM	6.12	Inhibition of RSK1 (unknown origin)	34375113
Serine/threonine-protein kinase Sgk1	IC50	=	1009.0	nM	6.0	Inhibition of SGK (unknown origin)	34375113
Unchecked	IC50	=	1030.0	nM	5.99	Antiproliferative activity against human 95-D cells assessed as inhibition of ce...	34375113
786-0	IC50	=	2500.0	nM	5.6	Antiproliferative activity against human 786-0 cells assessed as inhibition of c...	34375113
OVCAR-8	IC50	=	3520.0	nM	5.45	Antiproliferative activity against human OVCAR-8 cells assessed as inhibition of...	34375113
HepG2	IC50	=	3600.0	nM	5.44	Antiproliferative activity against human HepG2 cells assessed as inhibition of c...	34375113
SK-OV-3	IC50	=	4710.0	nM	5.33	Antiproliferative activity against human SK-OV-3 cells assessed as inhibition of...	34375113
L02	IC50	=	5400.0	nM	5.27	Antiproliferative activity against human HL7702 cells assessed as inhibition of ...	34375113
U-251	IC50	=	6530.0	nM	5.18	Antiproliferative activity against human U251 cells assessed as inhibition of ce...	34375113
A549	IC50	=	6560.0	nM	5.18	Antiproliferative activity against human A549 cells assessed as inhibition of ce...	34375113
KHOS/NP	IC50	=	7470.0	nM	5.13	Antiproliferative activity against human KHOS cells assessed as inhibition of ce...	34375113

Literature References

PubMed	DOI	Target Context	# Activities
34375113	10.1021/acs.jmedchem.1c00815	ADMET	66
34375113	10.1021/acs.jmedchem.1c00815	Unchecked	6
34375113	10.1021/acs.jmedchem.1c00815	KHOS/NP	5
34375113	10.1021/acs.jmedchem.1c00815	786-0	4
30856328	10.1021/acs.jmedchem.8b01635	RAW264.7	2
34375113	10.1021/acs.jmedchem.1c00815	HaCaT	2
34375113	10.1021/acs.jmedchem.1c00815	Cytochrome P450 2C19	1
34375113	10.1021/acs.jmedchem.1c00815	[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial	1
34375113	10.1021/acs.jmedchem.1c00815	Ribosomal protein S6 kinase alpha-5	1
34375113	10.1021/acs.jmedchem.1c00815	Serine/threonine-protein kinase Sgk1	1
34375113	10.1021/acs.jmedchem.1c00815	Ribosomal protein S6 kinase beta-1	1
34375113	10.1021/acs.jmedchem.1c00815	Ribosomal protein S6 kinase alpha-1	1
34375113	10.1021/acs.jmedchem.1c00815	Rho-associated protein kinase 1	1
34375113	10.1021/acs.jmedchem.1c00815	Protein kinase C theta type	1
34375113	10.1021/acs.jmedchem.1c00815	Protein kinase C eta type	1
34375113	10.1021/acs.jmedchem.1c00815	RAC-gamma serine/threonine-protein kinase	1
34375113	10.1021/acs.jmedchem.1c00815	cGMP-dependent protein kinase 2	1
34375113	10.1021/acs.jmedchem.1c00815	Voltage-gated inwardly rectifying potassium channel KCNH2	1
34375113	10.1021/acs.jmedchem.1c00815	HGC-27	1
34375113	10.1021/acs.jmedchem.1c00815	RAC-beta serine/threonine-protein kinase	1

Data from ChEMBL 36 via Core Engine