Compound Detail

CHEMBL4087968

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Nc1ccc(F)cc1NC(=O)c1ccc(CNC(=O)/C=C/c2cccnc2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4087968
Phase	Preclinical
Structure Type	MOL
InChI Key	WXHHICFWKXDFOW-BJMVGYQFSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

390.4

MW (Da)

3.38

ALogP

HBA

HBD

97.1

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	C22H19FN4O2
MW	390.42
Aromatic Rings	3
Heavy Atoms	29
NP-Likeness	-1.44

Activity Summary

IC50 89 meas. best 7.18

EC50 1 meas. best 5.85

Kd 1 meas. best 4.74

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histone deacetylase 2 CHEMBL1937	IC50	7.18	6.3988	66.5	8
Histone deacetylase 3 CHEMBL1829	IC50	7.17	7.17	67.0	2
Histone deacetylase 1 CHEMBL325	IC50	7.13	6.6373	74.0	11
Polyamine deacetylase HDAC10 CHEMBL5103	IC50	7.11	7.11	78.0	2
HCT-116 CHEMBL394	IC50	6.7	5.8271	202.0	7
Histone deacetylase 3/NCoR1 CHEMBL3038484	IC50	6.63	6.63	234.0	1
MV4-11 CHEMBL613835	IC50	6.5	6.5	320.0	1
Histone deacetylase 11 CHEMBL3310	IC50	6.37	6.37	432.0	1
HL-60 CHEMBL383	IC50	6.32	6.105	480.0	2
KG-1 CHEMBL612264	IC50	6.31	6.31	490.0	1
Friend leukemia cell line CHEMBL614499	IC50	6.3	6.3	500.0	1
A549 CHEMBL392	IC50	6.18	5.3175	665.0	4
Histone deacetylase 8 CHEMBL3192	IC50	6.13	6.13	733.0	1
RS4-11 CHEMBL2366159	IC50	6.09	6.09	810.0	1
Histone deacetylase CHEMBL2093865	IC50	6.05	5.9867	900.0	3
K562 CHEMBL385	IC50	6.01	5.34	975.0	2
Human immunodeficiency virus 1 CHEMBL378	EC50	5.85	5.85	1400.0	1
BaF3 CHEMBL614524	IC50	5.82	5.82	1500.0	1
NB-4 CHEMBL614188	IC50	5.72	5.72	1900.0	1
PC-3 CHEMBL390	IC50	5.68	5.68	2093.0	1
Unchecked CHEMBL612545	IC50	5.68	5.0625	2100.0	4
NIH3T3 CHEMBL614822	IC50	5.62	5.62	2370.0	2
HeLa CHEMBL399	IC50	5.47	5.018	3420.0	5
MDA-MB-231 CHEMBL400	IC50	5.47	5.455	3410.0	2
A-375 CHEMBL613859	IC50	5.39	5.276	4110.0	5
RPMI-8226 CHEMBL614882	IC50	5.38	5.38	4190.0	1
DOHH-2 CHEMBL2366181	IC50	5.37	5.37	4300.0	1
U-266 CHEMBL2366315	IC50	5.32	5.32	4810.0	1
EL4 CHEMBL614293	IC50	5.28	5.28	5200.0	1
MGC-803 CHEMBL3706566	IC50	5.19	5.19	6440.0	2
Raji CHEMBL614628	IC50	5.16	5.16	6900.0	1
Histone deacetylase 6 CHEMBL1865	IC50	5.15	5.1433	7110.0	3
SMMC-7721 CHEMBL613831	IC50	5.06	4.825	8630.0	2
HepG2 CHEMBL395	IC50	4.93	4.785	11670.0	2
NCI-H460 CHEMBL396	IC50	4.88	4.88	13340.0	1
NCI-H1299 CHEMBL612255	IC50	4.79	4.79	16260.0	1
Histone deacetylase 1 CHEMBL325	Kd	4.74	4.74	18300.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	4.5	4.5	32000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histone deacetylase 2	IC50	=	66.5	nM	7.18	Inhibition of recombinant human HDAC2 using FLUOR-DE-LYS-Green as substrate incu...	32361064
Histone deacetylase 3	IC50	=	67.0	nM	7.17	Inhibition of HDAC3 (unknown origin)	31536895
Histone deacetylase 3	IC50	=	67.0	nM	7.17	Inhibition of human recombinant HDAC3 incubated for 17 hrs	33035922
Histone deacetylase 1	IC50	=	74.0	nM	7.13	Inhibition of C-terminal 6His-FLAG-tagged human recombinant HDAC1 (1 to 482 resi...	38048697
Histone deacetylase 1	IC50	=	75.5	nM	7.12	Inhibition of HDAC1 (unknown origin) using BocLys(acetyl)-AMC as substrate incub...	37995564
Polyamine deacetylase HDAC10	IC50	=	78.0	nM	7.11	Inhibition of HDAC10 (unknown origin)	31536895
Polyamine deacetylase HDAC10	IC50	=	78.0	nM	7.11	Inhibition of human recombinant HDAC10 incubated for 17 hrs	33035922
Histone deacetylase 1	IC50	=	95.0	nM	7.02	Inhibition of HDAC1 (unknown origin)	31536895
Histone deacetylase 1	IC50	=	95.0	nM	7.02	Inhibition of human recombinant HDAC1 incubated for 17 hrs	33035922
Histone deacetylase 2	IC50	=	160.0	nM	6.8	Inhibition of human recombinant HDAC2 incubated for 17 hrs	33035922
Histone deacetylase 2	IC50	=	160.0	nM	6.8	Inhibition of HDAC2 (unknown origin)	31536895
Histone deacetylase 1	IC50	=	160.0	nM	6.8	Inhibition of HDAC1 (unknown origin)	32088129
Histone deacetylase 1	IC50	=	190.0	nM	6.72	Inhibition of human recombinant His-tagged HDAC1 (482 residues) expressed in bac...	31003060
Histone deacetylase 1	IC50	=	190.0	nM	6.72	Inhibition of recombinant human His tagged HDAC1 expressed in baculovirus infect...	31103900
HCT-116	IC50	=	202.0	nM	6.7	Antiproliferative activity against human HCT116 cells after 48 to 72 hrs by MTT ...	28532668
Histone deacetylase 3/NCoR1	IC50	=	234.0	nM	6.63	Inhibition of recombinant human HDAC3/NCOR1 assessed as decrease in deacetylatio...	31103900
Histone deacetylase 1	IC50	=	260.0	nM	6.58	Inhibition of recombinant human HDAC1 using SIRT1 as substrate incubated for 10 ...	32361064
Histone deacetylase 2	IC50	=	310.0	nM	6.51	Inhibition of recombinant human HDAC2 assessed as decrease in deacetylation of F...	31103900
Histone deacetylase 2	IC50	=	310.0	nM	6.51	Inhibition of human recombinant His-tagged HDAC2 (1 to 582 residues) expressed i...	31003060
MV4-11	IC50	=	320.0	nM	6.5	Antiproliferative activity against human MV4-11 cells assessed as reduction in c...	38048697

Literature References

PubMed	DOI	Target Context	# Activities
31103900	10.1016/j.ejmech.2019.05.007	A549	27
31003060	10.1016/j.ejmech.2019.04.017	SMMC-7721	26
29202397	10.1016/j.ejmech.2017.08.041	SMMC-7721	22
28391133	10.1016/j.ejmech.2017.03.038	A549	16
32361064	10.1016/j.ejmech.2020.112322	NCI-H460	7
32361064	10.1016/j.ejmech.2020.112322	HCT-116	7
32361064	10.1016/j.ejmech.2020.112322	HeLa	5
32361064	10.1016/j.ejmech.2020.112322	A-375	5
28532668	10.1016/j.bmcl.2017.05.026	Histone deacetylase 1	4
31991336	10.1016/j.ejmech.2020.112073	HCT-116	4
31991336	10.1016/j.ejmech.2020.112073	NCI-H460	4
31103900	10.1016/j.ejmech.2019.05.007	HCT-116	3
31003060	10.1016/j.ejmech.2019.04.017	HeLa	3
29202397	10.1016/j.ejmech.2017.08.041	MGC-803	3
29202397	10.1016/j.ejmech.2017.08.041	A-375	3
29202397	10.1016/j.ejmech.2017.08.041	HeLa	3
31103900	10.1016/j.ejmech.2019.05.007	HeLa	3
31003060	10.1016/j.ejmech.2019.04.017	A-375	3
31103900	10.1016/j.ejmech.2019.05.007	A-375	3
31003060	10.1016/j.ejmech.2019.04.017	HCT-116	3

Data from ChEMBL 36 via Core Engine