Compound Detail

CHEMBL4536105

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COc1ncc(-c2cc(OCCCCCCC(=O)NO)c3ncnc(C)c3c2)cc1F

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4536105
Phase	Preclinical
Structure Type	MOL
InChI Key	BQKQDMVFQZHPJZ-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

428.5

MW (Da)

3.98

ALogP

HBA

HBD

106.5

PSA (Å²)

0.29

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C22H25FN4O4
MW	428.46
Aromatic Rings	3
Heavy Atoms	31
NP-Likeness	-0.74

Activity Summary

IC50 47 meas. best 8.85

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histone deacetylase 2 CHEMBL1937	IC50	8.85	8.685	1.4	2
Histone deacetylase 8 CHEMBL3192	IC50	8.85	8.3	1.4	2
Histone deacetylase 1 CHEMBL325	IC50	8.85	8.85	1.4	4
Histone deacetylase 6 CHEMBL1865	IC50	8.18	8.18	6.6	2
PI3-kinase p110-delta/p85-alpha CHEMBL2111432	IC50	8.09	8.09	8.1	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform CHEMBL3130	IC50	8.09	8.09	8.1	1
Unchecked CHEMBL612545	IC50	8.09	8.09	8.1	1
Jurkat CHEMBL397	IC50	7.64	7.64	23.0	1
Ramos CHEMBL614629	IC50	7.64	7.64	23.0	1
BaF3 CHEMBL614524	IC50	7.64	7.64	23.0	1
EL4 CHEMBL614293	IC50	7.64	7.64	23.0	1
NB-4 CHEMBL614188	IC50	7.64	7.64	23.0	1
A20 CHEMBL613850	IC50	7.64	7.64	23.0	1
YAC-1 CHEMBL612814	IC50	7.64	7.64	23.0	1
U-937 CHEMBL612794	IC50	7.64	7.64	23.0	1
HL-60 CHEMBL383	IC50	7.64	7.64	23.0	1
K562 CHEMBL385	IC50	7.64	6.405	23.0	2
L1210 CHEMBL386	IC50	7.64	7.64	23.0	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	IC50	7.38	7.38	42.0	3
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform CHEMBL3267	IC50	7.17	7.17	67.0	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform CHEMBL3145	IC50	7.0	7.0	101.0	1
HGC-27 CHEMBL1075463	IC50	6.96	6.96	110.0	1
HCT-116 CHEMBL394	IC50	6.82	6.82	150.0	1
MV4-11 CHEMBL613835	IC50	6.6	6.6	250.0	1
MDA-MB-453 CHEMBL614334	IC50	6.52	6.52	300.0	1
HCT-8 CHEMBL613510	IC50	6.5	6.5	320.0	1
Capan-2 CHEMBL1075417	IC50	6.37	6.37	430.0	1
DU-145 CHEMBL613508	IC50	6.27	6.27	540.0	1
SW1990 CHEMBL1075592	IC50	6.05	6.05	900.0	1
NCI-H1299 CHEMBL612255	IC50	6.0	6.0	1000.0	1
HepG2 CHEMBL395	IC50	5.96	5.96	1100.0	1
MCF7 CHEMBL387	IC50	5.7	5.7	2000.0	1
Huh-7 CHEMBL614039	IC50	5.6	5.6	2500.0	1
Serine/threonine-protein kinase mTOR CHEMBL2842	IC50	5.54	5.54	2861.0	1
NCI-H460 CHEMBL396	IC50	5.52	5.52	3000.0	1
U-87 MG CHEMBL614247	IC50	5.5	5.5	3200.0	1
Bel-7402 CHEMBL614279	IC50	5.28	5.28	5200.0	1
THP-1 CHEMBL614245	IC50	5.27	5.27	5400.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	551.0	ng.hr.mL-1	Mus musculus
AUC	230.0	ng.hr.mL-1	Mus musculus
AUC	558.0	ng.hr.mL-1	Mus musculus
AUC	274.0	ng.hr.mL-1	Mus musculus
CL	90.0	mL.min-1.kg-1	Mus musculus
Cmax	7120.85	nM	Mus musculus
Cmax	333.75	nM	Mus musculus
F	4.2	%	Mus musculus
T1/2	0.33	hr	Mus musculus
T1/2	2.07	hr	Mus musculus
T1/2	1.2	hr	Mus musculus
T1/2	0.41	hr	Mus musculus
Tmax	0.03	hr	Mus musculus
Tmax	0.3	hr	Mus musculus
Vd	2.57	L.kg-1	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histone deacetylase 1	IC50	=	1.4	nM	8.85	Inhibition of human HDAC1 by fluorogenic assay	36503229
Histone deacetylase 1	IC50	=	1.4	nM	8.85	Inhibition of C-terminal 6His-FLAG-tagged human recombinant HDAC1 (1 to 482 resi...	38048697
Histone deacetylase 1	IC50	=	1.4	nM	8.85	Inhibition of HDAC1 (unknown origin)	37875056
Histone deacetylase 2	IC50	=	1.4	nM	8.85	Inhibition of HDAC2 (unknown origin)	37875056
Histone deacetylase 8	IC50	=	1.4	nM	8.85	Inhibition of HDAC8 (unknown origin)	37875056
Histone deacetylase 1	IC50	=	1.4	nM	8.85	Inhibition of recombinant C-terminal His/FLAG-tagged HDAC1 (unknown origin) expr...	31117517
Histone deacetylase 2	IC50	=	3.0	nM	8.52	Inhibition of recombinant human full length HDAC2 expressed in baculovirus infec...	31117517
Histone deacetylase 6	IC50	=	6.6	nM	8.18	Inhibition of HDAC6 (unknown origin) using Ac-peptide as substrate preincubated ...	31117517
Histone deacetylase 6	IC50	=	6.6	nM	8.18	Inhibition of human HDAC6 by fluorogenic assay	36503229
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform	IC50	=	8.1	nM	8.09	Inhibition of human PI3Kdelta by ADP-Glo luminescent kinase assay	36503229
Unchecked	IC50	=	8.1	nM	8.09	Inhibition of PI3K (unknown origin)	37875056
PI3-kinase p110-delta/p85-alpha	IC50	=	8.1	nM	8.09	Inhibition of recombinant human His-tagged PIK3CD/PIK3R1 expressed in baculoviru...	31117517
Histone deacetylase 8	IC50	=	18.0	nM	7.75	Inhibition of recombinant human full length C-terminal His-tagged HDAC8 expresse...	31117517
A20	IC50	=	23.0	nM	7.64	Antiproliferative activity against mouse A20 cells assessed as inhibition of cel...	37875056
BaF3	IC50	=	23.0	nM	7.64	Antiproliferative activity against mouse BaF3 cells assessed as inhibition of ce...	37875056
Ramos	IC50	=	23.0	nM	7.64	Antiproliferative activity against human Ramos cells assessed as inhibition of c...	37875056
YAC-1	IC50	=	23.0	nM	7.64	Antiproliferative activity against mouse YAC-1 cells assessed as inhibition of c...	37875056
Jurkat	IC50	=	23.0	nM	7.64	Antiproliferative activity against human Jurkat cells assessed as inhibition of ...	37875056
K562	IC50	=	23.0	nM	7.64	Antiproliferative activity against human K562 cells assessed as inhibition of ce...	37875056
HL-60	IC50	=	23.0	nM	7.64	Antiproliferative activity against human HL-60 cells assessed as inhibition of c...	37875056

Literature References

PubMed	DOI	Target Context	# Activities
31117517	10.1021/acs.jmedchem.9b00390	ADMET	40
31117517	10.1021/acs.jmedchem.9b00390	HCT-116	19
31117517	10.1021/acs.jmedchem.9b00390	Unchecked	13
31117517	10.1021/acs.jmedchem.9b00390	Mus musculus	6
31117517	10.1021/acs.jmedchem.9b00390	HGC-27	4
31117517	10.1021/acs.jmedchem.9b00390	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	2
37875056	10.1016/j.ejmech.2023.115879	EL4	2
31117517	10.1021/acs.jmedchem.9b00390	Histone deacetylase	2
37875056	10.1016/j.ejmech.2023.115879	A20	2
31117517	10.1021/acs.jmedchem.9b00390	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	2
31117517	10.1021/acs.jmedchem.9b00390	Histone deacetylase 2	1
31117517	10.1021/acs.jmedchem.9b00390	Histone deacetylase 6	1
31117517	10.1021/acs.jmedchem.9b00390	Histone deacetylase 8	1
31117517	10.1021/acs.jmedchem.9b00390	Histone deacetylase 11	1
31117517	10.1021/acs.jmedchem.9b00390	Serine/threonine-protein kinase mTOR	1
31117517	10.1021/acs.jmedchem.9b00390	PI3-kinase p110-delta/p85-alpha	1
31117517	10.1021/acs.jmedchem.9b00390	THP-1	1
31117517	10.1021/acs.jmedchem.9b00390	MCF7	1
31117517	10.1021/acs.jmedchem.9b00390	MDA-MB-453	1
31117517	10.1021/acs.jmedchem.9b00390	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform	1

Data from ChEMBL 36 via Core Engine