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Compound Detail

CHEMBL154574

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O=C(/C=C/c1ccccc1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL154574
Phase Preclinical
Structure Type MOL
InChI Key UVDDFTZLVFIQFL-VOTSOKGWSA-N
9
Targets
16
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

163.2
MW (Da)
1.21
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.39
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C9H9NO2
MW 163.18
Aromatic Rings 1
Heavy Atoms 12
NP-Likeness 0.08

Activity Summary

IC50 14 meas. best 7.66
EC50 2 meas. best 6.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 7.66 7.66 21.7 2
Histone deacetylase 1
CHEMBL325
 IC50 6.88 6.88 133.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 6.82 6.82 151.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 6.34 6.335 457.0 2
Histone deacetylase 8
CHEMBL3192
 IC50 6.14 6.13 725.0 2
Hepatitis C virus
CHEMBL379
 EC50 6.07 5.885 860.0 2
MDA-MB-231
CHEMBL400
 IC50 5.05 5.05 8980.0 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL312
 IC50 4.92 4.92 12000.0 3
Histone deacetylase 4
CHEMBL3524
 IC50 4.71 4.71 19460.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 6.2 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 22.0 nM 7.66 Inhibition of HDAC6 (unknown origin) assessed as fluorescence intensity measured... 23368884
Histone deacetylase 6 IC50 = 21.7 nM 7.66 HDAC Inhibition Assay: All histone deacetylases were purchased from BPS Bioscien... -
Histone deacetylase 1 IC50 = 133.0 nM 6.88 HDAC Inhibition Assay: All histone deacetylases were purchased from BPS Bioscien... -
Histone deacetylase 3 IC50 = 151.0 nM 6.82 HDAC Inhibition Assay: All histone deacetylases were purchased from BPS Bioscien... -
Histone deacetylase 2 IC50 = 457.0 nM 6.34 Inhibition of HDAC2 (unknown origin) assessed as fluorescence intensity measured... 23368884
Histone deacetylase 2 IC50 = 470.0 nM 6.33 HDAC Inhibition Assay: All histone deacetylases were purchased from BPS Bioscien... -
Histone deacetylase 8 IC50 = 725.0 nM 6.14 HDAC Inhibition Assay: All histone deacetylases were purchased from BPS Bioscien... -
Histone deacetylase 8 IC50 = 759.0 nM 6.12 Inhibition of HDAC8 (unknown origin) assessed as fluorescence intensity measured... 23368884
Hepatitis C virus EC50 = 860.0 nM 6.07 Antiviral activity against HCV genotype 1b infected in human Huh7 cells after 3 ... 25490700
Hepatitis C virus EC50 = 2000.0 nM 5.7 Antiviral activity against HCV infected in human HuH7-luc/neo cells assessed as ... 31201063
MDA-MB-231 IC50 = 8980.0 nM 5.05 Cytotoxicity against human MDA-MB-231 cells assessed as decrease in cell prolife... 28262526
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 12000.0 nM 4.92 In vitro inhibitory activity against 5-lipoxygenase in rat basophilic leukemia c... 2308149
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 12022.64 nM 4.92 Logarithmic value of inhibitory concentration against 5-lipoxygenase in rat baso... 2308149
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 12000.0 nM 4.92 In vitro inhibitory activity against RBL-1 5-LO 3820229
Histone deacetylase 4 IC50 = 19460.0 nM 4.71 Inhibition of HDAC4 (unknown origin) assessed as fluorescence intensity measured... 23368884

Literature References

PubMed DOI Target Context # Activities
20017493 10.1021/jm901502p Histone deacetylase 3
35307568 10.1016/j.bmcl.2022.128692 Mycobacteroides abscessus 2
35307568 10.1016/j.bmcl.2022.128692 Mycobacterium marinum 2
35307568 10.1016/j.bmcl.2022.128692 Mycobacterium tuberculosis 2
2308149 10.1021/jm00165a017 Polyunsaturated fatty acid 5-lipoxygenase 2
25490700 10.1021/jm501330g ADMET 2
28262526 10.1016/j.bmcl.2017.01.080 MDA-MB-231 2
25490700 10.1021/jm501330g Hepatitis C virus 1
31201063 10.1016/j.bmcl.2019.06.006 Hepatitis C virus 1
35307568 10.1016/j.bmcl.2022.128692 BMDM 1
31201063 10.1016/j.bmcl.2019.06.006 Histone deacetylase 3 1
31201063 10.1016/j.bmcl.2019.06.006 Histone deacetylase 2 1
31201063 10.1016/j.bmcl.2019.06.006 Histone deacetylase 1 1
23368884 10.1021/jm301355j Histone deacetylase 2 1
23368884 10.1021/jm301355j Histone deacetylase 4 1
23368884 10.1021/jm301355j Histone deacetylase 6 1
23368884 10.1021/jm301355j Histone deacetylase 8 1
19821586 10.1021/jm900648x No relevant target 1
19821586 10.1021/jm900648x Plasma 1
3820229 10.1021/jm00386a022 Polyunsaturated fatty acid 5-lipoxygenase 1

Data from ChEMBL 36 via Core Engine