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Compound Detail

CHEMBL4550214

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O=C(NO)c1ccc(Cn2c(=O)n(CCc3ccccc3)c(=O)c3ccccc32)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4550214
Phase Preclinical
Structure Type MOL
InChI Key JBJIKUXUKSADFV-UHFFFAOYSA-N
9
Targets
18
Activities
2
Assay Types
4
PK Parameters
16
Publications
0
Known Names

Molecular Properties

415.4
MW (Da)
2.57
ALogP
6
HBA
2
HBD
93.3
PSA (Ų)
0.37
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H21N3O4
MW 415.45
Aromatic Rings 4
Heavy Atoms 31
NP-Likeness -1.07

Activity Summary

IC50 16 meas. best 8.4
Ki 2 meas. best 8.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 Ki 8.8 8.615 1.6 2
Histone deacetylase 6
CHEMBL1865
 IC50 8.4 8.3825 4.0 4
Maternal embryonic leucine zipper kinase
CHEMBL4578
 IC50 6.7 6.7 200.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.51 6.48 309.0 3
Unchecked
CHEMBL612545
 IC50 5.81 5.81 1560.0 1
NIH3T3
CHEMBL614822
 IC50 5.29 5.29 5100.0 1
A549
CHEMBL392
 IC50 5.1 5.1 7870.0 1
Lewis lung carcinoma cell line
CHEMBL614088
 IC50 5.1 5.1 7870.0 1
Histone deacetylase 1
CHEMBL325
 IC50 4.95 4.95 11160.0 2
Histone deacetylase 11
CHEMBL3310
 IC50 4.86 4.86 13900.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 1335.0 hr.ng/g Mus musculus
AUC 6395.0 hr.ng/g Mus musculus
AUC 1903.0 hr.ng/g Mus musculus
AUC 71.0 hr.ng/g Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 Ki = 1.6 nM 8.8 Competitive inhibition of human full-length recombinant HDAC6 expressed in bacul... 30525585
Histone deacetylase 6 Ki = 3.7 nM 8.43 Competitive inhibition of human HDAC6 CD2 expressed in Escherichia coli BL21 (RI... 30525585
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of human HDAC6 expressed in baculovirus expression system in Sf9 cell... 37463500
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Enzymatic Assay: The IC50 values for aforementioned compounds against HDACs were... -
Histone deacetylase 6 IC50 = 4.0 nM 8.4 Inhibition of human full-length recombinant HDAC6 expressed in baculovirus infec... 30525585
Histone deacetylase 6 IC50 = 4.7 nM 8.33 Inhibition of HDAC6 (unknown origin) 32331933
Maternal embryonic leucine zipper kinase IC50 = 200.0 nM 6.7 Inhibition of MELK (unknown origin) 32331933
Histone deacetylase 8 IC50 = 309.0 nM 6.51 Inhibition of human full-length recombinant HDAC8 expressed in baculovirus infec... 30525585
Histone deacetylase 8 IC50 = 309.0 nM 6.51 Inhibition of human HDAC8 expressed in baculovirus expression system in Sf9 cell... 37463500
Histone deacetylase 8 IC50 = 376.0 nM 6.42 Enzymatic Assay: The IC50 values for aforementioned compounds against HDACs were... -
Unchecked IC50 = 1560.0 nM 5.81 Antiproliferative activity against human U-87 MG cells incubated for 72 hrs by M... 35786935
NIH3T3 IC50 = 5100.0 nM 5.29 Antiproliferative activity against mouse NIH3T3 cells assessed as reduction in c... 37463500
A549 IC50 = 7870.0 nM 5.1 Cytotoxicity against human A549 cells after 72 hrs by MTT assay 30525585
Lewis lung carcinoma cell line IC50 = 7870.0 nM 5.1 Cytotoxicity against mouse LL/2 cells after 72 hrs by MTT assay 30525585
Histone deacetylase 1 IC50 = 11160.0 nM 4.95 Inhibition of human full-length recombinant HDAC1 expressed in baculovirus infec... 30525585
Histone deacetylase 1 IC50 = 11160.0 nM 4.95 Enzymatic Assay: The IC50 values for aforementioned compounds against HDACs were... -
Histone deacetylase 11 IC50 = 13900.0 nM 4.86 Inhibition of human full-length recombinant HDAC11 expressed in baculovirus infe... 30525585
Histone deacetylase 11 IC50 = 13900.0 nM 4.86 Enzymatic Assay: The IC50 values for aforementioned compounds against HDACs were... -

Literature References

PubMed DOI Target Context # Activities
30525585 10.1021/acs.jmedchem.8b01590 ADMET 26
30525585 10.1021/acs.jmedchem.8b01590 Lewis lung carcinoma cell line 19
30525585 10.1021/acs.jmedchem.8b01590 Histone deacetylase 6 16
30525585 10.1021/acs.jmedchem.8b01590 A549 9
37463500 10.1021/acs.jmedchem.3c00644 NIH3T3 3
30525585 10.1021/acs.jmedchem.8b01590 Histone deacetylase 1 2
30525585 10.1021/acs.jmedchem.8b01590 Histone deacetylase 8 2
30525585 10.1021/acs.jmedchem.8b01590 Histone deacetylase 11 1
30525585 10.1021/acs.jmedchem.8b01590 Unchecked 1
32331933 10.1016/j.bmcl.2020.127202 Histone deacetylase 6 1
32331933 10.1016/j.bmcl.2020.127202 Unchecked 1
32331933 10.1016/j.bmcl.2020.127202 Maternal embryonic leucine zipper kinase 1
35786935 10.1021/acs.jmedchem.1c01946 Unchecked 1
37463500 10.1021/acs.jmedchem.3c00644 Histone deacetylase 1 1
37463500 10.1021/acs.jmedchem.3c00644 Histone deacetylase 6 1
37463500 10.1021/acs.jmedchem.3c00644 Histone deacetylase 8 1

Data from ChEMBL 36 via Core Engine