Compound Detail

CHEMBL379849

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O=C1/C(=C/c2ccccc2F)CNC/C1=C\c1ccccc1F

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL379849
Phase	Preclinical
Structure Type	MOL
InChI Key	NIVYQYSNRUIFIF-KAVGSWPWSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

311.3

MW (Da)

3.60

ALogP

HBA

HBD

29.1

PSA (Å²)

0.86

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C19H15F2NO
MW	311.33
Aromatic Rings	2
Heavy Atoms	23
NP-Likeness	-0.60

Activity Summary

IC50 55 meas. best 7.55

EC50 1 meas. best 6.7

Kd 1 meas. best 5.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Dual specificity tyrosine-phosphorylation-regulated kinase 2 CHEMBL4376	IC50	7.55	7.55	28.0	1
Trypanosoma brucei CHEMBL612849	EC50	6.7	6.7	200.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.54	5.8	290.0	3
A2780 CHEMBL614004	IC50	6.3	6.245	500.0	2
RAC-beta serine/threonine-protein kinase CHEMBL2431	IC50	6.14	6.14	720.0	1
Vascular endothelial growth factor receptor 2 CHEMBL279	IC50	6.11	6.11	770.0	1
RAC-alpha serine/threonine-protein kinase CHEMBL4282	IC50	6.11	6.11	780.0	1
SGC-7901 CHEMBL614909	IC50	6.0	5.595	1000.0	2
Unchecked CHEMBL612545	IC50	5.96	5.476	1100.0	5
NCI-H460 CHEMBL396	IC50	5.92	5.57	1200.0	2
NCI-H1975 CHEMBL614348	IC50	5.89	5.89	1300.0	1
DLD-1 CHEMBL614285	IC50	5.89	5.89	1300.0	1
A549 CHEMBL392	IC50	5.89	5.5525	1300.0	4
PANC-1 CHEMBL614139	IC50	5.82	5.82	1500.0	1
MDA-MB-435 CHEMBL614697	IC50	5.82	5.82	1500.0	1
HCT-116 CHEMBL394	IC50	5.82	5.82	1500.0	1
HT-29 CHEMBL384	IC50	5.8	5.8	1600.0	1
NCI-H1650 CHEMBL1075518	IC50	5.77	5.305	1700.0	2
518A2 CHEMBL4483222	IC50	5.75	5.75	1800.0	1
HeLa 229 CHEMBL4483246	IC50	5.72	5.72	1900.0	1
MGC-803 CHEMBL3706566	IC50	5.7	5.7	2000.0	1
HepG2 CHEMBL395	IC50	5.48	5.48	3330.0	1
U-251 CHEMBL615022	IC50	5.35	5.35	4500.0	1
CHO CHEMBL613853	IC50	5.34	5.34	4600.0	1
QGY-7703 CHEMBL4296490	IC50	5.3	5.3	4970.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 2 CHEMBL4376	Kd	5.3	5.3	5000.0	1
L02 CHEMBL4296457	IC50	5.29	5.1733	5100.0	3
MDA-MB-231 CHEMBL400	IC50	5.25	5.25	5600.0	1
Lewis lung carcinoma cell line CHEMBL614088	IC50	5.08	5.08	8400.0	1
SMMC-7721 CHEMBL613831	IC50	5.06	5.06	8800.0	1
Mitogen-activated protein kinase 1 CHEMBL4040	IC50	4.89	4.89	13000.0	1
Dual specificity mitogen-activated protein kinase kinase 1 CHEMBL3587	IC50	4.89	4.89	12800.0	1
Ribosomal protein S6 kinase beta-1 CHEMBL4501	IC50	4.7	4.7	20000.0	1
Mycobacterium tuberculosis CHEMBL360	IC50	4.7	4.5667	20000.0	3
RAF proto-oncogene serine/threonine-protein kinase CHEMBL1906	IC50	4.62	4.62	24000.0	1
Mycobacterium marinum CHEMBL614987	IC50	4.6	4.6	25000.0	1
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 CHEMBL2111345	IC50	4.34	4.34	46000.0	1
Inhibitor of nuclear factor kappa-B kinase subunit beta CHEMBL1991	IC50	4.14	4.14	72000.0	1
Serine/threonine-protein kinase Nek1 CHEMBL5855	IC50	4.11	4.11	77000.0	1
Mitogen-activated protein kinase 14 CHEMBL260	IC50	4.04	4.04	92000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	0.9651	ng.hr.mL-1	Mus musculus
AUC	0.5604	ng.hr.mL-1	Mus musculus
AUC	238.26	ng.hr.mL-1	Mus musculus
AUC	107.6	ng.hr.mL-1	Mus musculus
Cmax	883.31	nM	Mus musculus
Cmax	831.91	nM	Mus musculus
T1/2	1.0	hr	Mus musculus
T1/2	2.95	hr	Mus musculus
T1/2	3.65	hr	Mus musculus
Tmax	0.05	hr	Mus musculus
Tmax	0.05	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Dual specificity tyrosine-phosphorylation-regulated kinase 2	IC50	=	28.0	nM	7.55	Inhibition of human recombinant DYRK2 using KKISGRLSPIMTEQ as substrate incubate...	38746900
Trypanosoma brucei	EC50	=	200.0	nM	6.7	Antitrypanosomal activity against Trypanosoma brucei Lister 427 assessed as para...	36608774
NON-PROTEIN TARGET	IC50	=	290.0	nM	6.54	Cytotoxicity against human NB4 cells assessed as reduction in cell viability aft...	24960549
NON-PROTEIN TARGET	IC50	=	320.0	nM	6.5	Cytotoxicity against human NB4-R1 cells assessed as reduction in cell viability ...	24960549
A2780	IC50	=	500.0	nM	6.3	Cell viability of human cisplatin-sensitive human A2780 cells after 24 hrs by MT...	17684018
A2780	IC50	=	650.0	nM	6.19	Cell viability of cisplatin-resistant human A2780 cells after 24 hrs by MTT assa...	17684018
RAC-beta serine/threonine-protein kinase	IC50	=	720.0	nM	6.14	Inhibition of recombinant AKT2 (unknown origin) by FRET-based Z'-LYTE assay	23550937
Vascular endothelial growth factor receptor 2	IC50	=	770.0	nM	6.11	Inhibition of recombinant KDR (unknown origin) by FRET-based Z'-LYTE assay	23550937
RAC-alpha serine/threonine-protein kinase	IC50	=	780.0	nM	6.11	Inhibition of recombinant AKT1 (unknown origin) by FRET-based Z'-LYTE assay	23550937
SGC-7901	IC50	=	1000.0	nM	6.0	Antiproliferative activity against human SGC7901 cells after 72 hrs by MTT assay	29351887
Unchecked	IC50	=	1100.0	nM	5.96	Cytotoxicity against human KB-V1/Vbl cells after 72 hrs by MTT assay	28774574
NCI-H460	IC50	=	1200.0	nM	5.92	Cytotoxicity against human H460 cells assessed as reduction in cell viability af...	29655083
A549	IC50	=	1300.0	nM	5.89	Inhibition of NF-kappaB nuclear translocation in human A549 cells	19854644
DLD-1	IC50	=	1300.0	nM	5.89	Cytotoxicity against human DLD1 cells after 72 hrs by MTT assay	28774574
NCI-H1975	IC50	=	1300.0	nM	5.89	Cytotoxicity against human NCI-H1975 cells assessed as reduction in cell viabili...	29655083
Unchecked	IC50	=	1400.0	nM	5.85	Cytotoxicity against human U87 cells after 72 hrs by MTT assay	28774574
HCT-116	IC50	=	1500.0	nM	5.82	Cytotoxicity against human HCT116 cells after 72 hrs by MTT assay	28774574
MDA-MB-435	IC50	=	1500.0	nM	5.82	Cytotoxicity against human MDA-MB-435 cells	19854644
PANC-1	IC50	=	1500.0	nM	5.82	Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay	28774574
HT-29	IC50	=	1600.0	nM	5.8	Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay	28774574

Literature References

PubMed	DOI	Target Context	# Activities
17684018	10.1074/jbc.m703796200	A2780	53
28774574	10.1016/j.bmc.2017.07.039	HT-29	15
28774574	10.1016/j.bmc.2017.07.039	Unchecked	14
25618016	10.1016/j.ejmech.2015.01.020	Mus musculus	10
20638855	10.1016/j.bmc.2010.06.055	NCI-H441	8
25442312	10.1016/j.bmcl.2014.09.074	ADMET	7
25442312	10.1016/j.bmcl.2014.09.074	MDCK	6
29655083	10.1016/j.ejmech.2018.03.051	Unchecked	4
25618016	10.1016/j.ejmech.2015.01.020	Mycobacterium tuberculosis	3
28774574	10.1016/j.bmc.2017.07.039	PANC-1	2
28774574	10.1016/j.bmc.2017.07.039	HCT-116	2
28774574	10.1016/j.bmc.2017.07.039	DLD-1	2
24960549	10.1021/jm401352a	NON-PROTEIN TARGET	2
25618016	10.1016/j.ejmech.2015.01.020	Mycobacterium marinum	2
38746900	10.1021/acsmedchemlett.4c00065	Dual specificity tyrosine-phosphorylation-regulated kinase 2	2
28774574	10.1016/j.bmc.2017.07.039	518A2	2
23550937	10.1021/jm4002692	Mitogen-activated protein kinase 14	1
23550937	10.1021/jm4002692	MAP kinase-activated protein kinase 2	1
38746900	10.1021/acsmedchemlett.4c00065	MDA-MB-231	1
19854644	10.1016/j.bmcl.2009.10.023	MDA-MB-435	1

Data from ChEMBL 36 via Core Engine