Compound Detail

CHEMBL4749146

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O=C(NO)c1ccc(CCCN2CCC(CN[C@H]3C[C@@H]3c3ccccc3)CC2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4749146
Phase	Preclinical
Structure Type	MOL
InChI Key	HACUHRDPZRXYSI-RPWUZVMVSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

407.6

MW (Da)

3.60

ALogP

HBA

HBD

64.6

PSA (Å²)

0.44

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C25H33N3O2
MW	407.56
Aromatic Rings	2
Heavy Atoms	30
NP-Likeness	-0.82

Activity Summary

IC50 17 meas. best 8.3

EC50 4 meas. best 8.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
MM1.S CHEMBL4296471	EC50	8.7	8.55	2.0	2
Lysine-specific histone demethylase 1A CHEMBL6136	IC50	8.3	8.2733	5.0	3
Unchecked CHEMBL612545	EC50	8.22	8.22	6.0	1
Histone deacetylase 6 CHEMBL1865	IC50	7.32	7.2667	48.0	3
Histone deacetylase 8 CHEMBL3192	IC50	7.15	7.15	71.0	1
RPMI-8226 CHEMBL614882	EC50	6.55	6.55	280.0	1
Histone deacetylase 5 CHEMBL2563	IC50	5.94	5.94	1140.0	1
Unchecked CHEMBL612545	IC50	5.75	5.75	1780.0	1
Histone deacetylase 1 CHEMBL325	IC50	5.47	5.47	3400.0	1
Histone deacetylase 9 CHEMBL4145	IC50	5.46	5.46	3430.0	1
Histone deacetylase 7 CHEMBL2716	IC50	5.45	5.45	3580.0	1
Histone deacetylase 2 CHEMBL1937	IC50	5.4	5.4	3950.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.25	5.25	5600.0	1
Amine oxidase [flavin-containing] B CHEMBL2039	IC50	5.18	5.18	6600.0	1
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) CHEMBL2111363	IC50	5.13	5.13	7470.0	1
Amine oxidase [flavin-containing] A CHEMBL1951	IC50	5.07	5.07	8600.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	1520.0	ng.hr.mL-1	Mus musculus
CL	233.0	mL.min-1.kg-1	Mus musculus
Cmax	2014.43	nM	Mus musculus
Cmax	2218.08	nM	Mus musculus
F	44.0	%	Mus musculus
Fu	0.45	-	Not specified
T1/2	3.3	hr	Mus musculus
T1/2	2.5	hr	Mus musculus
Vd	66.0	L.kg-1	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
MM1.S	EC50	=	2.0	nM	8.7	Antiproliferative activity against human MM1.S cells assessed as reduction in ce...	33359604
MM1.S	EC50	=	4.0	nM	8.4	Antiproliferative activity against human MM1.S cells assessed as reduction in ce...	33359604
Lysine-specific histone demethylase 1A	IC50	=	5.0	nM	8.3	Inhibition of LSD1 (unknown origin)	33359604
Lysine-specific histone demethylase 1A	IC50	=	5.0	nM	8.3	Inhibition of LSD1 (unknown origin)	34915312
Unchecked	EC50	=	6.0	nM	8.22	Antiproliferative activity against human MM1.R cells assessed as reduction in ce...	33359604
Lysine-specific histone demethylase 1A	IC50	=	6.0	nM	8.22	Inhibition of LSD1 (unknown origin)	33359604
Histone deacetylase 6	IC50	=	48.0	nM	7.32	Inhibition of human HDAC6 (unknown origin) using RHKKAc as substrate by fluoresc...	33359604
Histone deacetylase 6	IC50	=	48.0	nM	7.32	Inhibition of HDAC6 (unknown origin)	34915312
Histone deacetylase 6	IC50	=	69.0	nM	7.16	Inhibition of human HDAC6 (unknown origin) using RHKKAc as substrate by fluoresc...	33359604
Histone deacetylase 8	IC50	=	71.0	nM	7.15	Inhibition of human HDAC8 using RHKAcKAc as substrate by fluorescence method	33359604
RPMI-8226	EC50	=	280.0	nM	6.55	Antiproliferative activity against human RPMI-8226 cells assessed as reduction i...	33359604
Histone deacetylase 5	IC50	=	1140.0	nM	5.94	Inhibition of human HDAC5 using Boc-Lys(trifluoroacetyl)-AMC as substrate by flu...	33359604
Unchecked	IC50	=	1780.0	nM	5.75	Inhibition of HDAC phosphorylation (unknown origin)	33359604
Histone deacetylase 1	IC50	=	3400.0	nM	5.47	Inhibition of human HDAC1 using RHKKAc as substrate by fluorescence method	33359604
Histone deacetylase 9	IC50	=	3430.0	nM	5.46	Inhibition of human HDAC9 using Boc-Lys(trifluoroacetyl)-AMC as substrate by flu...	33359604
Histone deacetylase 7	IC50	=	3580.0	nM	5.45	Inhibition of human HDAC7 using Boc-Lys(trifluoroacetyl)-AMC as substrate by flu...	33359604
Histone deacetylase 2	IC50	=	3950.0	nM	5.4	Inhibition of human HDAC2 using RHKKAc as substrate by fluorescence method	33359604
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	5600.0	nM	5.25	Inhibition of human ERG	33359604
Amine oxidase [flavin-containing] B	IC50	=	6600.0	nM	5.18	Inhibition of MAO-B (unknown origin)	33359604
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	IC50	=	7470.0	nM	5.13	Inhibition of human HDAC3/NCOR2 using RHKKAc as substrate by fluorescence method	33359604

Literature References

PubMed	DOI	Target Context	# Activities
33359604	10.1016/j.bmcl.2020.127763	ADMET	21
33359604	10.1016/j.bmcl.2020.127763	Histone deacetylase 6	5
33359604	10.1016/j.bmcl.2020.127763	Lysine-specific histone demethylase 1A	5
33359604	10.1016/j.bmcl.2020.127763	Unchecked	4
33359604	10.1016/j.bmcl.2020.127763	Histone deacetylase 1	3
33359604	10.1016/j.bmcl.2020.127763	MM1.S	3
34915312	10.1016/j.ejmech.2021.114042	Histone deacetylase 6	1
33359604	10.1016/j.bmcl.2020.127763	Cytochrome P450 2D6	1
33359604	10.1016/j.bmcl.2020.127763	Cytochrome P450 3A4	1
33359604	10.1016/j.bmcl.2020.127763	No relevant target	1
33359604	10.1016/j.bmcl.2020.127763	Voltage-gated inwardly rectifying potassium channel KCNH2	1
33359604	10.1016/j.bmcl.2020.127763	Amine oxidase [flavin-containing] B	1
33359604	10.1016/j.bmcl.2020.127763	Amine oxidase [flavin-containing] A	1
33359604	10.1016/j.bmcl.2020.127763	RPMI-8226	1
33359604	10.1016/j.bmcl.2020.127763	Polyamine deacetylase HDAC10	1
33359604	10.1016/j.bmcl.2020.127763	Histone deacetylase 9	1
33359604	10.1016/j.bmcl.2020.127763	Histone deacetylase 8	1
33359604	10.1016/j.bmcl.2020.127763	Histone deacetylase 7	1
33359604	10.1016/j.bmcl.2020.127763	Histone deacetylase 5	1
33359604	10.1016/j.bmcl.2020.127763	Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)	1

Data from ChEMBL 36 via Core Engine