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Compound Detail

CHEMBL3935992

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O=C(NO)c1cnc(NC2(c3ccccc3)CCC(F)(F)CC2)nc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3935992
Phase Preclinical
Structure Type MOL
InChI Key MRWCVKLVSWYIFO-UHFFFAOYSA-N
13
Targets
28
Activities
2
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

348.4
MW (Da)
3.11
ALogP
5
HBA
3
HBD
87.1
PSA (Ų)
0.58
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H18F2N4O2
MW 348.35
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.78

Activity Summary

IC50 27 meas. best 8.52
EC50 1 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 8.52 8.47 3.0 6
Histone deacetylase 6
CHEMBL1865
 EC50 7.1 7.1 79.4 1
Histone deacetylase 6
CHEMBL2878
 IC50 6.4 6.4 398.1 1
Histone deacetylase 1
CHEMBL325
 IC50 6.11 5.806 780.0 5
Histone deacetylase 2
CHEMBL1937
 IC50 6.01 5.3825 982.0 4
Histone deacetylase 5
CHEMBL2563
 IC50 5.43 5.43 3700.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 5.36 4.71 4380.0 2
Histone deacetylase 7
CHEMBL2716
 IC50 5.19 5.19 6500.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 4.92 4.92 12000.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 4.89 4.89 13000.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 4.8 4.8 16000.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 4.75 4.75 18000.0 1
Histone deacetylase 9
CHEMBL4145
 IC50 4.72 4.72 19000.0 1
THP-1
CHEMBL614245
 IC50 4.03 4.015 94000.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 139.34 ng.hr.mL-1 Mus musculus
AUC 17.42 ng.hr.mL-1 Rattus norvegicus
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 0.14 mL.min-1.kg-1 Mus musculus
CL 0.18 mL.min-1.kg-1 Rattus norvegicus
F 12.0 % Mus musculus
F 19.0 % Rattus norvegicus
Fu 0.23 - Homo sapiens
T1/2 0.2 hr Mus musculus
T1/2 0.3 hr Rattus norvegicus
T1/2 1.7 hr Mus musculus
T1/2 2.1 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 3.0 nM 8.52 Inhibition of HDAC6 (unknown origin) using acetyl-lysine tripeptide as substrate... 32067866
Histone deacetylase 6 IC50 = 3.0 nM 8.52 Inhibition of HDAC6 (unknown origin) 32815366
Histone deacetylase 6 IC50 = 3.0 nM 8.52 Inhibition of HDAC6 (unknown origin) using acetyl-lysine tripeptide substrate as... 34992037
Histone deacetylase 6 IC50 = 3.7 nM 8.43 Enzyme Assay: Compounds for testing were diluted in DMSO to 50 fold the final co... -
Histone deacetylase 6 IC50 = 3.7 nM 8.43 HDAC Enzyme Assay: Compounds for testing were diluted in DMSO to 50 fold the fin... -
Histone deacetylase 6 IC50 = 3.981 nM 8.4 Inhibition of full length TEV-cleavable N-terminal His6-tagged human recombinant... 37797307
Histone deacetylase 6 EC50 = 79.43 nM 7.1 Inhibition of HDAC6 in human BEAS-2B cells assessed as deacetylation of acetylat... 37797307
Histone deacetylase 6 IC50 = 398.11 nM 6.4 Inhibition of HDAC6 in mouse LA-4 cells assessed as deacetylation of acetylated ... 37797307
Histone deacetylase 1 IC50 = 780.0 nM 6.11 Inhibition of HDAC1 (unknown origin) 32067866
Histone deacetylase 1 IC50 = 780.0 nM 6.11 Inhibition of HDAC1 (unknown origin) 32815366
Histone deacetylase 1 IC50 = 961.0 nM 6.02 Enzyme Assay: Compounds for testing were diluted in DMSO to 50 fold the final co... -
Histone deacetylase 1 IC50 = 961.0 nM 6.02 HDAC Enzyme Assay: Compounds for testing were diluted in DMSO to 50 fold the fin... -
Histone deacetylase 2 IC50 = 982.0 nM 6.01 Enzyme Assay: Compounds for testing were diluted in DMSO to 50 fold the final co... -
Histone deacetylase 2 IC50 = 982.0 nM 6.01 HDAC Enzyme Assay: Compounds for testing were diluted in DMSO to 50 fold the fin... -
Histone deacetylase 5 IC50 = 3700.0 nM 5.43 Inhibition of human recombinant HDAC5 incubated for 30 mins by fluorimetry analy... 37797307
Histone deacetylase 3 IC50 = 4380.0 nM 5.36 Enzyme Assay: Compounds for testing were diluted in DMSO to 50 fold the final co... -
Histone deacetylase 2 IC50 = 4380.0 nM 5.36 HDAC Enzyme Assay: Compounds for testing were diluted in DMSO to 50 fold the fin... -
Histone deacetylase 7 IC50 = 6500.0 nM 5.19 Inhibition of human recombinant HDAC7 incubated for 30 mins by fluorimetry analy... 37797307
Histone deacetylase 4 IC50 = 12000.0 nM 4.92 Inhibition of human recombinant HDAC4 incubated for 30 mins by fluorimetry analy... 37797307
Histone deacetylase 11 IC50 = 13000.0 nM 4.89 Inhibition of human recombinant HDAC11 incubated for 30 mins by fluorimetry anal... 37797307

Literature References

PubMed DOI Target Context # Activities
37797307 10.1021/acs.jmedchem.3c01269 ADMET 17
37797307 10.1021/acs.jmedchem.3c01269 Histone deacetylase 6 6
37797307 10.1021/acs.jmedchem.3c01269 THP-1 2
37797307 10.1021/acs.jmedchem.3c01269 Histone deacetylase 1 1
37797307 10.1021/acs.jmedchem.3c01269 Histone deacetylase 11 1
37797307 10.1021/acs.jmedchem.3c01269 Polyamine deacetylase HDAC10 1
37797307 10.1021/acs.jmedchem.3c01269 Histone deacetylase 9 1
37797307 10.1021/acs.jmedchem.3c01269 Histone deacetylase 7 1
37797307 10.1021/acs.jmedchem.3c01269 Histone deacetylase 5 1
37797307 10.1021/acs.jmedchem.3c01269 Histone deacetylase 4 1
37797307 10.1021/acs.jmedchem.3c01269 Histone deacetylase 8 1
37797307 10.1021/acs.jmedchem.3c01269 Histone deacetylase 3 1
37797307 10.1021/acs.jmedchem.3c01269 Histone deacetylase 2 1
32067866 10.1016/j.bmcl.2020.127023 Histone deacetylase 1 1
37797307 10.1021/acs.jmedchem.3c01269 No relevant target 1
34992037 10.1016/j.ejmech.2021.114090 Histone deacetylase 6 1
32815366 10.1021/acs.jmedchem.0c00567 Unchecked 1
32815366 10.1021/acs.jmedchem.0c00567 Histone deacetylase 6 1
32815366 10.1021/acs.jmedchem.0c00567 Histone deacetylase 1 1
32067866 10.1016/j.bmcl.2020.127023 Histone deacetylase 6 1

Data from ChEMBL 36 via Core Engine