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Compound Detail

CHEMBL55895

PHENYLBUTYRYLHYDROXAMIC ACID
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O=C(CCCc1ccccc1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL55895
Name PHENYLBUTYRYLHYDROXAMIC ACID
Phase Preclinical
Structure Type MOL
InChI Key UPHXPXYRKPCXHK-UHFFFAOYSA-N
8
Targets
19
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

179.2
MW (Da)
1.51
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.54
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 C10H13NO2
MW 179.22
Aromatic Rings 1
Heavy Atoms 13
NP-Likeness -0.25

Activity Summary

IC50 13 meas. best 6.3
Ki 6 meas. best 6.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 Ki 6.82 6.82 150.0 1
Histone deacetylase 1
CHEMBL325
 Ki 6.53 6.53 295.0 1
Histone deacetylase 2
CHEMBL1937
 Ki 6.37 6.37 430.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 6.3 6.3 500.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 6.22 6.22 600.0 1
Histone deacetylase 1
CHEMBL325
 IC50 6.22 6.22 600.0 1
Histone deacetylase 3
CHEMBL1829
 Ki 5.78 5.78 1650.0 1
Histone deacetylase 8
CHEMBL3192
 Ki 5.73 5.73 1850.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 5.7 5.7 2000.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 5.4 5.4 4000.0 1
Arachidonate 12-lipoxygenase
CHEMBL2741
 IC50 4.82 4.82 15000.0 1
Histone deacetylase 5
CHEMBL2563
 Ki 4.8 4.8 16000.0 1
Histone deacetylase 5
CHEMBL2563
 IC50 4.6 4.6 25000.0 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL312
 IC50 4.57 4.57 26915.3 3

Pharmacokinetic Data

Parameter Value Units Species
T1/2 2.0 hr Rattus norvegicus
T1/2 24.0 hr Homo sapiens
T1/2 24.0 hr -
T1/2 20.0 hr Rattus norvegicus
T1/2 30.9 hr Rattus norvegicus
T1/2 22.6 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 Ki = 150.0 nM 6.82 Inhibition of human HDAC6 20139990
Histone deacetylase 1 Ki = 295.0 nM 6.53 Inhibition of human HDAC1 20139990
Histone deacetylase 2 Ki = 430.0 nM 6.37 Inhibition of human HDAC2 20139990
Histone deacetylase 6 IC50 = 500.0 nM 6.3 Inhibition of human recombinant HDAC6 21874153
Histone deacetylase 1 IC50 = 600.0 nM 6.22 Inhibition of human recombinant HDAC1 21874153
Histone deacetylase 2 IC50 = 600.0 nM 6.22 Inhibition of human recombinant HDAC2 21874153
Histone deacetylase 3 Ki = 1650.0 nM 5.78 Inhibition of human HDAC3 20139990
Histone deacetylase 8 Ki = 1850.0 nM 5.73 Activity of human HDAC8 20139990
Histone deacetylase 3 IC50 = 2000.0 nM 5.7 Inhibition of human recombinant HDAC3 21874153
Histone deacetylase 8 IC50 = 4000.0 nM 5.4 Inhibition of human recombinant HDAC8 21874153
Arachidonate 12-lipoxygenase IC50 = 15000.0 nM 4.82 In vitro inhibition of rat platelet 12-lipoxygenase 2502629
Histone deacetylase 5 Ki = 16000.0 nM 4.8 Inhibition of human HDAC5 20139990
Histone deacetylase 5 IC50 = 25000.0 nM 4.6 Inhibition of human recombinant HDAC5 21874153
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 27000.0 nM 4.57 In vitro inhibitory activity against 5-lipoxygenase in rat basophilic leukemia c... 2308149
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 26915.35 nM 4.57 Logarithmic value of inhibitory concentration against 5-lipoxygenase in rat baso... 2308149
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 27000.0 nM 4.57 In vitro inhibitory activity against RBL-1 5-LO 3820229

Literature References

PubMed DOI Target Context # Activities
28985084 10.1021/acs.jmedchem.7b01444 Plasma 4
21874153 10.1021/ml1001954 Histone deacetylase 6 2
2308149 10.1021/jm00165a017 Polyunsaturated fatty acid 5-lipoxygenase 2
19821586 10.1021/jm900648x Plasma 2
19821586 10.1021/jm900648x No relevant target 2
2502629 10.1021/jm00128a027 Polyunsaturated fatty acid 5-lipoxygenase 2
20139990 10.1038/nchembio.313 Histone deacetylase 3 1
21874153 10.1021/ml1001954 Histone deacetylase 4 1
21874153 10.1021/ml1001954 Histone deacetylase 8 1
21874153 10.1021/ml1001954 Histone deacetylase 3 1
21874153 10.1021/ml1001954 Histone deacetylase 2 1
21874153 10.1021/ml1001954 Histone deacetylase 1 1
20139990 10.1038/nchembio.313 Histone deacetylase 8 1
20139990 10.1038/nchembio.313 Histone deacetylase 6 1
20139990 10.1038/nchembio.313 Histone deacetylase 5 1
20139990 10.1038/nchembio.313 Histone deacetylase 2 1
20139990 10.1038/nchembio.313 Histone deacetylase 1 1
3820229 10.1021/jm00386a022 Polyunsaturated fatty acid 5-lipoxygenase 1
2502629 10.1021/jm00128a027 Cavia porcellus 1
2502629 10.1021/jm00128a027 Mus musculus 1

Data from ChEMBL 36 via Core Engine