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Compound Detail

CHEMBL4796066

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O=C(NO)c1ccc(Nc2c3ccccc3nc3ccc(Br)cc23)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4796066
Phase Preclinical
Structure Type MOL
InChI Key PESSDQDERPAVNH-UHFFFAOYSA-N
13
Targets
21
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

408.3
MW (Da)
5.01
ALogP
4
HBA
3
HBD
74.2
PSA (Ų)
0.25
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H14BrN3O2
MW 408.26
Aromatic Rings 4
Heavy Atoms 26
NP-Likeness -0.91

Activity Summary

IC50 19 meas. best 7.58
EC50 2 meas. best 6.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 7.58 7.58 26.0 2
Histone deacetylase 1
CHEMBL325
 IC50 7.05 7.05 90.0 2
Histone deacetylase
CHEMBL2093865
 IC50 6.8 6.8 160.0 1
Class 1 histone deacetylase
CHEMBL4523988
 IC50 6.8 6.8 160.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 6.48 6.48 330.0 1
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 6.48 6.48 330.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 6.32 6.32 480.0 2
Class 1 histone deacetylase
CHEMBL4523988
 EC50 6.24 6.24 580.0 1
Acetylcholinesterase
CHEMBL220
 IC50 6.06 6.06 880.0 1
Amyloid-beta precursor protein
CHEMBL2487
 IC50 5.96 5.96 1100.0 1
Histone deacetylase 9
CHEMBL4145
 IC50 5.26 5.26 5510.0 2
Histone deacetylase 5
CHEMBL2563
 IC50 5.14 5.14 7190.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 5.11 5.11 7850.0 2
Histone deacetylase 6
CHEMBL1865
 EC50 5.1 5.1 8000.0 1
Histone deacetylase 7
CHEMBL2716
 IC50 5.04 5.04 9130.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.631 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 26.0 nM 7.58 Inhibition of recombinant human full-length N-terminal GST-tagged HDAC6 expresse... 32151835
Histone deacetylase 6 IC50 = 26.0 nM 7.58 Inhibition of N-terminal GST-tagged full length human HDAC6 expressed in baculov... 33845233
Histone deacetylase 1 IC50 = 90.0 nM 7.05 Inhibition of recombinant human C-terminal FLAG/His-tagged HDAC1 (1 to 482 resid... 32151835
Histone deacetylase 1 IC50 = 90.0 nM 7.05 Inhibition of HDAC1 (unknown origin) 33845233
Class 1 histone deacetylase IC50 = 160.0 nM 6.8 Inhibition of class 1 HDAC in human HeLa cell nuclear extract using Boc-Lys(Ac)-... 32151835
Histone deacetylase IC50 = 160.0 nM 6.8 Inhibition of HDAC in human HeLa nuclear extracts using Boc-Lys (acetyl)-AMC as ... 33845233
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 330.0 nM 6.48 Inhibition of human recombinant C-terminal His-tagged HDAC3 (1 to 428 residues)/... 32151835
Histone deacetylase 3 IC50 = 330.0 nM 6.48 Inhibition of HDAC3 (unknown origin) 33845233
Histone deacetylase 2 IC50 = 480.0 nM 6.32 Inhibition of HDAC2 (unknown origin) 33845233
Histone deacetylase 2 IC50 = 480.0 nM 6.32 Inhibition of recombinant human C-terminal His-tagged HDAC2 (1 to 488 residues) ... 32151835
Class 1 histone deacetylase EC50 = 580.0 nM 6.24 Inhibition of Class 1 HDAC in human Neuro2a cells assessed as increase in acetyl... 32151835
Acetylcholinesterase IC50 = 880.0 nM 6.06 Inhibition of recombinant human C-terminal 6His-tagged AChE (Glu32 to Leu614 res... 32151835
Amyloid-beta precursor protein IC50 = 1100.0 nM 5.96 Inhibition of amyloid beta (1 to 42) (unknown origin) self aggregation after 24 ... 32151835
Histone deacetylase 9 IC50 = 5510.0 nM 5.26 Inhibition of recombinant human C-terminal His-tagged HDAC9 (604 to 1066 residue... 32151835
Histone deacetylase 9 IC50 = 5510.0 nM 5.26 Inhibition of C-terminal His-tagged human HDAC9 (604 to 1066 residues) expressed... 33845233
Histone deacetylase 5 IC50 = 7190.0 nM 5.14 Inhibition of recombinant human C-terminal His-tagged HDAC5 (656 to 1122 residue... 32151835
Histone deacetylase 4 IC50 = 7850.0 nM 5.11 Inhibition of recombinant human N-terminal GST-tagged/C-terminal His-tagged HDAC... 32151835
Histone deacetylase 4 IC50 = 7850.0 nM 5.11 Inhibition of N-terminal GST-tagged and C-terminal His-tagged human HDAC4 (627 t... 33845233
Histone deacetylase 6 EC50 = 8000.0 nM 5.1 Inhibition of HDAC6 in human Neuro2a cells assessed as increase in alpha-tubulin... 32151835
Histone deacetylase 7 IC50 = 9130.0 nM 5.04 Inhibition of recombinant human N-terminal GST-tagged HDAC7 (518 to end residues... 32151835

Literature References

PubMed DOI Target Context # Activities
32151835 10.1016/j.ejmech.2020.112193 ADMET 5
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 6 3
32151835 10.1016/j.ejmech.2020.112193 Class 1 histone deacetylase 3
32151835 10.1016/j.ejmech.2020.112193 Unchecked 3
32151835 10.1016/j.ejmech.2020.112193 Amyloid-beta precursor protein 2
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 1
33845233 10.1016/j.ejmech.2021.113419 Histone deacetylase 3 1
33845233 10.1016/j.ejmech.2021.113419 Histone deacetylase 2 1
33845233 10.1016/j.ejmech.2021.113419 Histone deacetylase 1 1
33845233 10.1016/j.ejmech.2021.113419 Histone deacetylase 6 1
33845233 10.1016/j.ejmech.2021.113419 Histone deacetylase 9 1
33845233 10.1016/j.ejmech.2021.113419 Histone deacetylase 7 1
33845233 10.1016/j.ejmech.2021.113419 Histone deacetylase 4 1
33845233 10.1016/j.ejmech.2021.113419 Histone deacetylase 1
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 2 1
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 1 1
32151835 10.1016/j.ejmech.2020.112193 Acetylcholinesterase 1
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 9 1
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 5 1
32151835 10.1016/j.ejmech.2020.112193 Histone deacetylase 4 1

Data from ChEMBL 36 via Core Engine