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Compound Detail

CHEMBL3110015

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O=C(NO)[C@@H]1[C@H](c2ccccc2)[C@H]1c1ccc(-c2ncc(F)cn2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3110015
Phase Preclinical
Structure Type MOL
InChI Key QHCRWOYXPXJUJS-KZNAEPCWSA-N
9
Targets
20
Activities
2
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

349.4
MW (Da)
3.29
ALogP
4
HBA
2
HBD
75.1
PSA (Ų)
0.56
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 C20H16FN3O2
MW 349.37
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -0.54

Activity Summary

IC50 19 meas. best 7.52
Kd 1 meas. best 6.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 5
CHEMBL2563
 IC50 7.52 7.52 30.0 2
Histone deacetylase 4
CHEMBL3524
 IC50 7.3 6.962 50.0 5
Histone deacetylase 7
CHEMBL2716
 IC50 6.96 6.94 110.0 2
Histone deacetylase 4
CHEMBL3524
 Kd 6.96 6.96 110.0 1
Histone deacetylase 9
CHEMBL4145
 IC50 6.72 6.71 190.0 2
Histone deacetylase 8
CHEMBL3192
 IC50 5.85 5.85 1400.0 2
Histone deacetylase 6
CHEMBL1865
 IC50 5.72 5.72 1900.0 2
Histone deacetylase 3
CHEMBL1829
 IC50 5.03 5.03 9400.0 1
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 5.01 5.01 9700.0 1
Histone deacetylase 1
CHEMBL325
 IC50 4.68 4.68 21000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 42.0 mL.min-1.kg-1 Homo sapiens
CL 688.0 mL.min-1.kg-1 Mus musculus
CL 688.0 mL.min-1.kg-1 Mus musculus
CL 42.0 mL.min-1.kg-1 Homo sapiens
CL 183.33 mL.min-1.kg-1 Mus musculus
F 100.0 % Mus musculus
T1/2 0.3 hr Mus musculus
Tmax 0.5 hr Mus musculus
Tmax 0.5 hr Mus musculus
Tmax 0.5 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 5 IC50 = 30.0 nM 7.52 Inhibition of HDAC5 catalytic domain (unknown origin) using Boc-Lys(TFA)-AMC as ... 26819662
Histone deacetylase 5 IC50 = 30.0 nM 7.52 Inhibition of human recombinant HDAC5 catalytic domain using Boc_Lys_TFA as subs... 24261862
Histone deacetylase 4 IC50 = 50.0 nM 7.3 Inhibition of human recombinant HDAC4 catalytic domain using Boc_Lys_TFA as subs... 24261862
Histone deacetylase 4 IC50 = 50.0 nM 7.3 Inhibition of HDAC4 catalytic domain (unknown origin) using Boc-Lys(TFA)-AMC as ... 26819662
Histone deacetylase 4 IC50 = 60.0 nM 7.22 Inhibition Assay: 5 μl of each solution of 1:20 diluted compound from above is t... -
Histone deacetylase 4 Kd = 110.0 nM 6.96 Binding affinity to HDAC4 catalytic domain (unknown origin) by surface plasmon r... 26819662
Histone deacetylase 7 IC50 = 110.0 nM 6.96 Inhibition of human recombinant HDAC7 catalytic domain using Boc_Lys_TFA as subs... 24261862
Histone deacetylase 7 IC50 = 120.0 nM 6.92 Inhibition of HDAC7 catalytic domain (unknown origin) using Boc-Lys(TFA)-AMC as ... 26819662
Histone deacetylase 9 IC50 = 190.0 nM 6.72 Inhibition of human recombinant HDAC9 catalytic domain using Boc_Lys_TFA as subs... 24261862
Histone deacetylase 9 IC50 = 200.0 nM 6.7 Inhibition of HDAC9 catalytic domain (unknown origin) using Boc-Lys(TFA)-AMC as ... 26819662
Histone deacetylase 4 IC50 = 310.0 nM 6.51 Inhibition of HDAC4 in human Jurkat E6.1 cells using Boc-Lys-TFA as substrate in... 24261862
Histone deacetylase 4 IC50 = 330.0 nM 6.48 Inhibition of HDAC4 in human Jurkat E6-1 cells using Lys-TFA as substrate 26819662
Histone deacetylase 8 IC50 = 1400.0 nM 5.85 Inhibition of human recombinant full length HDAC8 using Boc_Lys_TFA as substrate... 24261862
Histone deacetylase 8 IC50 = 1400.0 nM 5.85 Inhibition of HDAC8 (unknown origin) using Boc-Lys(TFA)-AMC as substrate 26819662
Histone deacetylase 6 IC50 = 1900.0 nM 5.72 Inhibition of human recombinant full length HDAC6 after 60 mins by fluorescence ... 24261862
Histone deacetylase 6 IC50 = 1900.0 nM 5.72 Inhibition of HDAC6 (unknown origin) expressed in HEK cells using Boc-Lys(Ac)-AM... 26819662
Histone deacetylase 3 IC50 = 9400.0 nM 5.03 Inhibition of human recombinant full length HDAC3-NCoR2 using Lys_Ac_AMC as subs... 24261862
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 9700.0 nM 5.01 Inhibition of HDAC3/NCoR2 (unknown origin) using Boc-Lys(Ac)-AMC as substrate 26819662
Histone deacetylase 1 IC50 = 21000.0 nM 4.68 Inhibition of human recombinant full length HDAC1 using (Ac)Arg-Gly-Lys(Ac) as s... 24261862
Histone deacetylase 1 IC50 = 21000.0 nM 4.68 Inhibition of HDAC1 (unknown origin) using Boc-Lys(Ac)-AMC as substrate 26819662

Literature References

PubMed DOI Target Context # Activities
26819662 10.1021/acsmedchemlett.5b00302 Histone deacetylase 4 5
26819662 10.1021/acsmedchemlett.5b00302 Mus musculus 4
24261862 10.1021/jm4011884 ADMET 3
26819662 10.1021/acsmedchemlett.5b00302 Plasma 3
26819662 10.1021/acsmedchemlett.5b00302 Brain 3
26819662 10.1021/acsmedchemlett.5b00302 Muscle 3
24261862 10.1021/jm4011884 Histone deacetylase 4 3
26819662 10.1021/acsmedchemlett.5b00302 MDCK 2
24261862 10.1021/jm4011884 Histone deacetylase 8 1
24261862 10.1021/jm4011884 Histone deacetylase 3 1
24261862 10.1021/jm4011884 Histone deacetylase 9 1
24261862 10.1021/jm4011884 Histone deacetylase 7 1
24261862 10.1021/jm4011884 Histone deacetylase 5 1
26819662 10.1021/acsmedchemlett.5b00302 ADMET 1
26819662 10.1021/acsmedchemlett.5b00302 No relevant target 1
26819662 10.1021/acsmedchemlett.5b00302 Liver microsome 1
24261862 10.1021/jm4011884 Histone deacetylase 1 1
26819662 10.1021/acsmedchemlett.5b00302 Histone deacetylase 7 1
26819662 10.1021/acsmedchemlett.5b00302 Histone deacetylase 9 1
24261862 10.1021/jm4011884 Liver microsome 1

Data from ChEMBL 36 via Core Engine