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Compound Detail

CHEMBL16300

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

Basic Information

ChEMBL ID CHEMBL16300
Name BENZOHYDROXAMATE
Phase Preclinical
Structure Type MOL
InChI Key VDEUYMSGMPQMIK-UHFFFAOYSA-N
14
Targets
26
Activities
3
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

137.1
MW (Da)
0.81
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.44
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C7H7NO2
MW 137.14
Aromatic Rings 1
Heavy Atoms 10
NP-Likeness -0.71

Activity Summary

IC50 20 meas. best 6.94
Ki 5 meas. best 5.02
Kd 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 6.94 6.1433 115.0 3
Histone deacetylase 8
CHEMBL3192
 IC50 5.72 5.72 1920.0 1
Histone deacetylase 1
CHEMBL325
 IC50 5.33 4.8325 4730.0 4
Histone deacetylase 3
CHEMBL1829
 IC50 5.11 5.11 7830.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 5.1 5.1 7910.0 1
Carbonic anhydrase 12
CHEMBL3242
 Ki 5.02 5.02 9510.0 1
MDA-MB-231
CHEMBL400
 IC50 5.01 5.01 9850.0 1
Mandelate racemase
CHEMBL4739
 Ki 4.92 4.92 12000.0 1
Histone deacetylase 7
CHEMBL2716
 IC50 4.81 4.81 15600.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 4.8 4.8 16000.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.77 4.76 17000.0 2
Carbonic anhydrase 9
CHEMBL3594
 Ki 4.34 4.34 45900.0 1
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 4.14 4.14 71572.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 4.08 4.08 83100.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 24.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 115.0 nM 6.94 Inhibition of HDAC6 (unknown origin) assessed as fluorescence intensity measured... 23368884
Histone deacetylase 6 IC50 = 1343.0 nM 5.87 Inhibition of recombinant human full length N-terminal GST-tagged HDAC6 expresse... 34795871
Histone deacetylase 8 IC50 = 1920.0 nM 5.72 Inhibition of HDAC8 (unknown origin) assessed as fluorescence intensity measured... 23368884
Histone deacetylase 6 IC50 = 2370.0 nM 5.62 Inhibition of recombinant full length human N-terminal GST-tagged HDAC6 expresse... 31710483
Histone deacetylase 1 IC50 = 4730.0 nM 5.33 Inhibition of HDAC1 (unknown origin) assessed as fluorescence intensity measured... 23368884
Histone deacetylase 3 IC50 = 7830.0 nM 5.11 Inhibition of HDAC3 (unknown origin) assessed as fluorescence intensity measured... 23368884
Histone deacetylase 2 IC50 = 7910.0 nM 5.1 Inhibition of HDAC2 (unknown origin) assessed as fluorescence intensity measured... 23368884
Carbonic anhydrase 12 Ki = 9510.0 nM 5.02 Inhibition of recombinant human carbonic anhydrase 12 catalytic domain preincuba... 28658574
MDA-MB-231 IC50 = 9850.0 nM 5.01 Cytotoxicity against human MDA-MB-231 cells assessed as decrease in cell prolife... 28262526
Mandelate racemase Ki = 12000.0 nM 4.92 Inhibition of mandelate racemase in Pseudomonas putida 17055725
Histone deacetylase 7 IC50 = 15600.0 nM 4.81 Inhibition of HDAC7 (unknown origin) assessed as fluorescence intensity measured... 23368884
Indoleamine 2,3-dioxygenase 1 IC50 = 16000.0 nM 4.8 Inhibition of recombinant human IDO1 assessed as reduction in kynurenine product... 26717206
Plasmodium falciparum IC50 = 17000.0 nM 4.77 Antimicrobial activity against Plasmodium falciparum 20185316
Plasmodium falciparum IC50 = 17600.0 nM 4.75 In vitro antimalarial activity against Plasmodium falciparum 7608896
Histone deacetylase 1 IC50 = 20000.0 nM 4.7 Inhibition of HDAC1 17576064
Histone deacetylase 1 IC50 = 20000.0 nM 4.7 Inhibition of human HDAC1 expressed in domain of SMRT 17555962
Histone deacetylase 1 IC50 = 25380.0 nM 4.6 Inhibition of recombinant human C-terminal His-tagged HDAC1 expressed in Sf9 ins... 34795871
Carbonic anhydrase 9 Ki = 45900.0 nM 4.34 Inhibition of recombinant human carbonic anhydrase 9 catalytic domain preincubat... 28658574
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 71572.0 nM 4.14 Inhibition of C-terminal His-tagged human HDAC3 (1 to 428 residues)/N-terminal G... 31710483
Carbonic anhydrase 1 Ki = 83100.0 nM 4.08 Inhibition of recombinant human carbonic anhydrase 1 preincubated for 15 mins pr... 28658574

Literature References

PubMed DOI Target Context # Activities
17157014 10.1016/j.bmcl.2006.11.053 Unchecked 3
20017493 10.1021/jm901502p Histone deacetylase 3
2308149 10.1021/jm00165a017 Polyunsaturated fatty acid 5-lipoxygenase 2
23368884 10.1021/jm301355j Histone deacetylase 2 2
23368884 10.1021/jm301355j Histone deacetylase 3 2
23368884 10.1021/jm301355j Histone deacetylase 1 2
23368884 10.1021/jm301355j Histone deacetylase 6 2
458812 10.1021/jm00191a027 L1210 2
28262526 10.1016/j.bmcl.2017.01.080 MDA-MB-231 2
17157014 10.1016/j.bmcl.2006.11.053 Metallo-beta-lactamase type 2 2
17555962 10.1016/j.bmcl.2007.05.080 Histone deacetylase 1 1
19112024 10.1016/j.bmc.2008.11.075 unidentified influenza virus 1
19821586 10.1021/jm900648x Plasma 1
19821586 10.1021/jm900648x No relevant target 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1
21859126 10.1021/jm200794r Micrococcus luteus 1
17055725 10.1016/j.bmcl.2006.09.079 Mandelate racemase 1
3820229 10.1021/jm00386a022 Polyunsaturated fatty acid 5-lipoxygenase 1
36262388 10.1021/acsmedchemlett.2c00272 Histone deacetylase 2 1
12646026 10.1021/jm020334u Polymerase acidic protein 1

Data from ChEMBL 36 via Core Engine