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Compound Detail

CHEMBL4160840

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O=C(NO)c1ccc(-c2ccnc(Nc3ccc(N4CCOCC4)cc3)n2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4160840
Phase Preclinical
Structure Type MOL
InChI Key FEWZFWICBIRTLY-UHFFFAOYSA-N
12
Targets
12
Activities
1
Assay Types
2
PK Parameters
16
Publications
0
Known Names

Molecular Properties

391.4
MW (Da)
2.84
ALogP
7
HBA
3
HBD
99.6
PSA (Ų)
0.45
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H21N5O3
MW 391.43
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -1.57

Activity Summary

IC50 12 meas. best 7.35

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 3/NCoR1
CHEMBL3038484
 IC50 7.35 7.35 45.0 1
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 7.16 7.16 69.0 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 7.07 7.07 85.0 1
Histone deacetylase 1
CHEMBL325
 IC50 6.8 6.8 160.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 6.38 6.38 419.0 1
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 IC50 6.38 6.38 419.0 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 6.29 6.29 517.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.21 6.21 609.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 5.77 5.77 1704.0 1
HEL
CHEMBL613888
 IC50 5.46 5.46 3500.0 1
K562
CHEMBL385
 IC50 5.4 5.4 4000.0 1
HL-60
CHEMBL383
 IC50 5.21 5.21 6100.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 83.8 mL.min-1.g-1 Mus musculus
T1/2 0.275 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 3/NCoR1 IC50 = 45.0 nM 7.35 Inhibition of human recombinant HDAC3/GST-tagged NCOR1 (397 to 503 residues) co-... 29940115
Tyrosine-protein kinase JAK1 IC50 = 69.0 nM 7.16 Inhibition of JAK1 (unknown origin) using FAM-labeled peptide as substrate prein... 29940115
Tyrosine-protein kinase JAK2 IC50 = 85.0 nM 7.07 Inhibition of JAK2 (unknown origin) using FAM-labeled peptide as substrate prein... 29940115
Histone deacetylase 1 IC50 = 160.0 nM 6.8 Inhibition of full length human recombinant HDAC1 expressed in baculovirus expre... 29940115
Non-receptor tyrosine-protein kinase TYK2 IC50 = 419.0 nM 6.38 Inhibition of TYK2 (unknown origin) using FAM-labeled peptide as substrate prein... 29940115
Histone deacetylase 6 IC50 = 419.0 nM 6.38 Inhibition of full length human recombinant HDAC6 expressed in Baculovirus infec... 29940115
Tyrosine-protein kinase JAK3 IC50 = 517.0 nM 6.29 Inhibition of JAK3 (unknown origin) using FAM-labeled peptide as substrate prein... 29940115
Histone deacetylase 8 IC50 = 609.0 nM 6.21 Inhibition of full length recombinant C-terminal His tagged human HDAC8 expresse... 29940115
Histone deacetylase 2 IC50 = 1704.0 nM 5.77 Inhibition of recombinant HDAC2 (unknown origin) using (Ac-Leu-Gly-Lys(Ac)-AMC a... 29940115
HEL IC50 = 3500.0 nM 5.46 Antiproliferative activity against human HEL cells after 48 hrs by CCK-8 assay 29940115
K562 IC50 = 4000.0 nM 5.4 Antiproliferative activity against human K562 cells after 48 hrs by CCK-8 assay 29940115
HL-60 IC50 = 6100.0 nM 5.21 Antiproliferative activity against human HL60 cells after 48 hrs by CCK-8 assay 29940115

Literature References

PubMed DOI Target Context # Activities
29940115 10.1021/acs.jmedchem.8b00393 Candida albicans 16
29940115 10.1021/acs.jmedchem.8b00393 HEL 9
29940115 10.1021/acs.jmedchem.8b00393 Mus musculus 4
29940115 10.1021/acs.jmedchem.8b00393 Tyrosine-protein kinase JAK2 2
29940115 10.1021/acs.jmedchem.8b00393 Histone deacetylase 2
29940115 10.1021/acs.jmedchem.8b00393 ADMET 2
29940115 10.1021/acs.jmedchem.8b00393 Histone deacetylase 1 1
29940115 10.1021/acs.jmedchem.8b00393 HL-60 1
29940115 10.1021/acs.jmedchem.8b00393 K562 1
29940115 10.1021/acs.jmedchem.8b00393 Tyrosine-protein kinase JAK1 1
29940115 10.1021/acs.jmedchem.8b00393 Tyrosine-protein kinase JAK3 1
29940115 10.1021/acs.jmedchem.8b00393 Non-receptor tyrosine-protein kinase TYK2 1
29940115 10.1021/acs.jmedchem.8b00393 Histone deacetylase 2 1
29940115 10.1021/acs.jmedchem.8b00393 Histone deacetylase 3/NCoR1 1
29940115 10.1021/acs.jmedchem.8b00393 Histone deacetylase 6 1
29940115 10.1021/acs.jmedchem.8b00393 Histone deacetylase 8 1

Data from ChEMBL 36 via Core Engine