Compound Detail

CHEMBL4060201

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O=C(CCCCCCn1cc(-c2ncnc3[nH]ccc23)cn1)NO

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4060201
Phase	Preclinical
Structure Type	MOL
InChI Key	YRRVLBINSXVLFM-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

328.4

MW (Da)

2.28

ALogP

HBA

HBD

108.7

PSA (Å²)

0.33

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C16H20N6O2
MW	328.38
Aromatic Rings	3
Heavy Atoms	24
NP-Likeness	-1.09

Activity Summary

IC50 29 meas. best 8.85

Kd 1 meas. best 5.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Histone deacetylase 6 CHEMBL1865	IC50	8.85	8.85	1.4	1
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) CHEMBL2111363	IC50	8.41	8.41	3.9	1
Histone deacetylase 2 CHEMBL1937	IC50	8.24	8.24	5.8	1
Histone deacetylase 1 CHEMBL325	IC50	8.16	8.16	6.9	1
Tyrosine-protein kinase JAK1 CHEMBL2835	IC50	7.77	7.77	17.0	1
Polyamine deacetylase HDAC10 CHEMBL5103	IC50	7.72	7.72	19.0	1
Histone deacetylase 11 CHEMBL3310	IC50	7.51	7.51	31.0	1
Tyrosine-protein kinase JAK2 CHEMBL2971	IC50	7.12	7.12	75.0	1
KG-1 CHEMBL612264	IC50	6.82	6.82	150.0	1
Non-receptor tyrosine-protein kinase TYK2 CHEMBL3553	IC50	6.73	6.73	188.0	1
Unchecked CHEMBL612545	IC50	6.35	6.0967	450.0	3
MV4-11 CHEMBL613835	IC50	6.34	6.34	460.0	1
Histone deacetylase 8 CHEMBL3192	IC50	6.33	6.33	469.0	1
Jurkat CHEMBL397	IC50	6.33	6.33	470.0	1
Tyrosine-protein kinase JAK3 CHEMBL2148	IC50	6.25	6.25	569.0	1
MOLM-14 CHEMBL3706570	IC50	6.13	6.13	740.0	1
MDA-MB-231 CHEMBL400	IC50	6.1	6.1	790.0	1
MCF7 CHEMBL387	IC50	6.08	6.08	840.0	1
HEL 92.1.7 CHEMBL4296425	IC50	5.88	5.88	1330.0	1
KMS-12-BM CHEMBL4296455	IC50	5.7	5.7	2020.0	1
OPM-2 CHEMBL2366353	IC50	5.67	5.67	2160.0	1
HCT-116 CHEMBL394	IC50	5.63	5.63	2320.0	1
PC-3 CHEMBL390	IC50	5.62	5.62	2410.0	1
TAMH CHEMBL4483280	IC50	5.33	5.33	4630.0	1
Tyrosine-protein kinase JAK2 CHEMBL2971	Kd	5.3	5.3	5000.0	1
HL-60 CHEMBL383	IC50	5.13	5.13	7360.0	1
Histone deacetylase 5 CHEMBL2563	IC50	4.98	4.98	10500.0	1
Histone deacetylase 7 CHEMBL2716	IC50	4.76	4.76	17200.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	175.2	ng.hr.mL-1	Rattus norvegicus
AUC	12.3	ng.hr.mL-1	Rattus norvegicus
CL	95.1	mL.min-1.kg-1	Rattus norvegicus
Cmax	48.42	nM	Rattus norvegicus
F	1.4	%	Rattus norvegicus
T1/2	3.333	hr	Rattus norvegicus
T1/2	0.35	hr	Rattus norvegicus
T1/2	0.58	hr	Rattus norvegicus
Tmax	0.083	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Histone deacetylase 6	IC50	=	1.4	nM	8.85	Inhibition of N-terminal GST tagged human HDAC6 (1 to 1215 residues) expressed i...	28953386
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	IC50	=	3.9	nM	8.41	Inhibition of human recombinant HDAC3 (1 to 428 residues)/N-terminal GST-tagged ...	28953386
Histone deacetylase 2	IC50	=	5.8	nM	8.24	Inhibition of C-terminal GST tagged human recombinant HDAC2 (1 to 488 residues) ...	28953386
Histone deacetylase 1	IC50	=	6.9	nM	8.16	Inhibition of C-terminal FLAG His tagged full length human recombinant HDAC1 (1 ...	28953386
Tyrosine-protein kinase JAK1	IC50	=	17.0	nM	7.77	Inhibition of human JAK1 using poly[Glu:Tyr] as substrate in presence of [gamma-...	28953386
Polyamine deacetylase HDAC10	IC50	=	19.0	nM	7.72	Inhibition of human HDAC10 using fluorogenic peptide from p53 residues 379 to 38...	28953386
Histone deacetylase 11	IC50	=	31.0	nM	7.51	Inhibition of C-terminal His tagged human recombinant HDAC11 (1 to 347 residues)...	28953386
Tyrosine-protein kinase JAK2	IC50	=	75.0	nM	7.12	Inhibition of human JAK2 using poly[Glu:Tyr] as substrate in presence of [gamma-...	28953386
KG-1	IC50	=	150.0	nM	6.82	Antiproliferative activity against human KG1 cells after 48 hrs by CellTiter-Glo...	28953386
Non-receptor tyrosine-protein kinase TYK2	IC50	=	188.0	nM	6.73	Inhibition of human TYK2 using KKSRGDYMTMQIG as substrate in presence of [gamma-...	28953386
Unchecked	IC50	=	450.0	nM	6.35	Antiproliferative activity against human NKYS cells after 48 hrs by CellTiter-Gl...	28953386
MV4-11	IC50	=	460.0	nM	6.34	Antiproliferative activity against human MV4-11 cells after 48 hrs by CellTiter-...	28953386
Histone deacetylase 8	IC50	=	469.0	nM	6.33	Inhibition of C-terminal His tagged human recombinant HDAC8 (1 to 377 residues) ...	28953386
Jurkat	IC50	=	470.0	nM	6.33	Antiproliferative activity against human Jurkat cells	28953386
Tyrosine-protein kinase JAK3	IC50	=	569.0	nM	6.25	Inhibition of human JAK3 using GEEEEYFELVKKKK as substrate in presence of [gamma...	28953386
Unchecked	IC50	=	570.0	nM	6.24	Antiproliferative activity against human KHYG cells after 48 hrs by CellTiter-Gl...	28953386
MOLM-14	IC50	=	740.0	nM	6.13	Antiproliferative activity against human MOLM14 cells after 48 hrs by CellTiter-...	28953386
MDA-MB-231	IC50	=	790.0	nM	6.1	Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT as...	28953386
MCF7	IC50	=	840.0	nM	6.08	Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay	28953386
HEL 92.1.7	IC50	=	1330.0	nM	5.88	Antiproliferative activity against human HEL 92.1.7 cells after 36 hrs by Presto...	28953386

Literature References

PubMed	DOI	Target Context	# Activities
28953386	10.1021/acs.jmedchem.7b00678	Unchecked	9
28953386	10.1021/acs.jmedchem.7b00678	Rattus norvegicus	9
28953386	10.1021/acs.jmedchem.7b00678	Histone deacetylase 6	4
28953386	10.1021/acs.jmedchem.7b00678	Tyrosine-protein kinase JAK2	4
28953386	10.1021/acs.jmedchem.7b00678	No relevant target	2
28953386	10.1021/acs.jmedchem.7b00678	Histone deacetylase 1	2
28953386	10.1021/acs.jmedchem.7b00678	Plasma	2
28953386	10.1021/acs.jmedchem.7b00678	MOLM-14	2
28953386	10.1021/acs.jmedchem.7b00678	KMS-12-BM	2
28953386	10.1021/acs.jmedchem.7b00678	Histone deacetylase 1/2/3	2
28953386	10.1021/acs.jmedchem.7b00678	Tyrosine-protein kinase JAK3	2
28953386	10.1021/acs.jmedchem.7b00678	Non-receptor tyrosine-protein kinase TYK2	2
28953386	10.1021/acs.jmedchem.7b00678	JAK2/JAK1	2
28953386	10.1021/acs.jmedchem.7b00678	Rho-associated protein kinase 2	1
28953386	10.1021/acs.jmedchem.7b00678	MDA-MB-231	1
28953386	10.1021/acs.jmedchem.7b00678	SRSF protein kinase 3	1
28953386	10.1021/acs.jmedchem.7b00678	Histone deacetylase 9	1
28953386	10.1021/acs.jmedchem.7b00678	Inhibitor of nuclear factor kappa-B kinase subunit beta	1
28953386	10.1021/acs.jmedchem.7b00678	Histone deacetylase 2	1
28953386	10.1021/acs.jmedchem.7b00678	Histone deacetylase 5	1

Data from ChEMBL 36 via Core Engine