Compound Detail

CHEMBL3917405

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O=C(CCCCCCOc1ccc2cc1COC/C=C/COCc1cccc(c1)-c1ccnc(n1)N2)NO

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL3917405
Phase	Preclinical
Structure Type	MOL
InChI Key	IYBYMTCQQMFOHB-AATRIKPKSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

518.6

MW (Da)

5.32

ALogP

HBA

HBD

114.8

PSA (Å²)

0.16

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C29H34N4O5
MW	518.61
Aromatic Rings	3
Heavy Atoms	38
NP-Likeness	0.18

Activity Summary

IC50 43 meas. best 8.85

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Tyrosine-protein kinase JAK2 CHEMBL2971	IC50	8.85	8.85	1.4	1
Histone deacetylase 6 CHEMBL1865	IC50	8.68	8.68	2.1	1
Tyrosine-protein kinase JAK3 CHEMBL2148	IC50	8.0	8.0	10.0	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform CHEMBL3267	IC50	8.0	8.0	10.0	1
Non-receptor tyrosine-protein kinase TYK2 CHEMBL3553	IC50	8.0	8.0	10.0	1
Histone deacetylase 2 CHEMBL1937	IC50	7.31	7.31	49.0	1
Polyamine deacetylase HDAC10 CHEMBL5103	IC50	7.1	7.1	80.0	1
Histone deacetylase 1 CHEMBL325	IC50	6.65	6.65	222.0	1
Histone deacetylase 8 CHEMBL3192	IC50	6.13	6.13	740.0	1
Histone deacetylase 11 CHEMBL3310	IC50	6.03	6.03	930.0	1
HEL 92.1.7 CHEMBL4296425	IC50	6.03	6.03	940.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.03	5.7493	940.0	14
Unchecked CHEMBL612545	IC50	5.97	5.87	1080.0	3
MOLM-14 CHEMBL3706570	IC50	5.94	5.94	1140.0	1
Jurkat CHEMBL397	IC50	5.92	5.92	1190.0	2
MDA-MB-231 CHEMBL400	IC50	5.84	5.84	1430.0	1
MCF7 CHEMBL387	IC50	5.83	5.83	1470.0	1
KG-1 CHEMBL612264	IC50	5.79	5.79	1630.0	1
PC-3 CHEMBL390	IC50	5.77	5.77	1700.0	1
OPM-2 CHEMBL2366353	IC50	5.69	5.69	2050.0	1
KMS-12-BM CHEMBL4296455	IC50	5.68	5.68	2110.0	2
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) CHEMBL2111363	IC50	5.66	5.66	2170.0	1
HCT-116 CHEMBL394	IC50	5.65	5.65	2230.0	1
HL-60 CHEMBL383	IC50	5.4	5.4	4000.0	1
TAMH CHEMBL4483280	IC50	5.02	5.02	9570.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	178.33	mL.min-1.kg-1	Rattus norvegicus
T1/2	0.2883	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Tyrosine-protein kinase JAK2	IC50	=	1.4	nM	8.85	Inhibition of JAK2 (unknown origin) preincubated for 20 mins followed by [33P]AT...	27541357
Histone deacetylase 6	IC50	=	2.1	nM	8.68	Inhibition of full length human recombinant N-terminal GST-tagged HDAC6 (1 to 12...	27541357
Non-receptor tyrosine-protein kinase TYK2	IC50	=	10.0	nM	8.0	Inhibition of human TYK2 (V877 to C1187 residues) expressed in mammalian express...	27541357
Tyrosine-protein kinase JAK3	IC50	=	10.0	nM	8.0	Inhibition of human JAK3 JH1 catalytic domain (I781 to S1124 residues) expressed...	27541357
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	IC50	=	10.0	nM	8.0	Inhibition of human PI3Kgamma (S144 to A1102 residues) expressed in mammalian ex...	27541357
Histone deacetylase 2	IC50	=	49.0	nM	7.31	Inhibition of full length human recombinant C-terminal GST-tagged HDAC2 (1 to 48...	27541357
Polyamine deacetylase HDAC10	IC50	=	80.0	nM	7.1	Inhibition of HDAC10 (unknown origin) preincubated with enzyme followed by fluor...	27541357
Histone deacetylase 1	IC50	=	222.0	nM	6.65	Inhibition of full length human recombinant C-terminal FLAG/His-tagged HDAC1 (1 ...	27541357
Histone deacetylase 8	IC50	=	740.0	nM	6.13	Inhibition of human recombinant C-terminal His-tagged HDAC8 (1 to 377 residues) ...	27541357
HEL 92.1.7	IC50	=	940.0	nM	6.03	Antiproliferative activity against human HEL 92.1.7 cells after 72 hrs by MTT as...	30243158
HEL 92.1.7	IC50	=	940.0	nM	6.03	Antiproliferative activity against human HEL 92.1.7 cells after 36 hrs by Presto...	28953386
Histone deacetylase 11	IC50	=	930.0	nM	6.03	Inhibition of human recombinant N-terminal His-tagged HDAC11 (1 to 347 residues)...	27541357
NON-PROTEIN TARGET	IC50	=	940.0	nM	6.03	Antiproliferative activity against HEL 92.1.7 cells harboring JAK2 V617F mutant ...	27541357
NON-PROTEIN TARGET	IC50	=	1080.0	nM	5.97	Antiproliferative activity against human NKYS cells after 48 hrs by CellTiter-Gl...	27541357
Unchecked	IC50	=	1080.0	nM	5.97	Antiproliferative activity against human NKYS cells after 48 hrs by CellTiter-Gl...	28953386
NON-PROTEIN TARGET	IC50	=	1090.0	nM	5.96	Antiproliferative activity against human KHYG cells after 48 hrs by CellTiter-Gl...	27541357
Unchecked	IC50	=	1090.0	nM	5.96	Antiproliferative activity against human KHYG cells after 48 hrs by CellTiter-Gl...	28953386
NON-PROTEIN TARGET	IC50	=	1140.0	nM	5.94	Antiproliferative activity against human MOLM14 cells harboring FLT3-ITD mutant ...	27541357
MOLM-14	IC50	=	1140.0	nM	5.94	Antiproliferative activity against human MOLM14 cells after 48 hrs by CellTiter-...	28953386
Jurkat	IC50	=	1190.0	nM	5.92	Antiproliferative activity against human Jurkat cells after 72 hrs by MTT assay	30243158

Literature References

PubMed	DOI	Target Context	# Activities
27541357	10.1021/acs.jmedchem.6b00157	Unchecked	37
27541357	10.1021/acs.jmedchem.6b00157	NON-PROTEIN TARGET	17
27541357	10.1021/acs.jmedchem.6b00157	MOLM-14	14
27541357	10.1021/acs.jmedchem.6b00157	Tyrosine-protein kinase JAK2	6
27541357	10.1021/acs.jmedchem.6b00157	Histone deacetylase 6	4
27541357	10.1021/acs.jmedchem.6b00157	Mast/stem cell growth factor receptor Kit	4
28953386	10.1021/acs.jmedchem.7b00678	Unchecked	4
27541357	10.1021/acs.jmedchem.6b00157	Histone deacetylase 1/2/3	3
27541357	10.1021/acs.jmedchem.6b00157	Non-receptor tyrosine-protein kinase TYK2	3
27541357	10.1021/acs.jmedchem.6b00157	Tyrosine-protein kinase JAK3	3
28953386	10.1021/acs.jmedchem.7b00678	HL-60	2
27541357	10.1021/acs.jmedchem.6b00157	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	2
27541357	10.1021/acs.jmedchem.6b00157	High affinity nerve growth factor receptor	2
27541357	10.1021/acs.jmedchem.6b00157	Mitogen-activated protein kinase 8	2
27541357	10.1021/acs.jmedchem.6b00157	Mitogen-activated protein kinase 10	2
27541357	10.1021/acs.jmedchem.6b00157	ADMET	2
30243158	10.1016/j.ejmech.2018.09.024	KMS-12-BM	1
27541357	10.1021/acs.jmedchem.6b00157	Histone deacetylase 5	1
27541357	10.1021/acs.jmedchem.6b00157	Histone deacetylase 7	1
27541357	10.1021/acs.jmedchem.6b00157	Histone deacetylase 8	1

Data from ChEMBL 36 via Core Engine