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Compound Detail

CHEMBL3692671

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CCCN(CCC)C[C@@H](C)NC(=O)c1ccc(-c2noc(C(F)(F)F)n2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3692671
Phase Preclinical
Structure Type MOL
InChI Key HMXFCVJIASWKMB-CYBMUJFWSA-N
11
Targets
21
Activities
2
Assay Types
1
PK Parameters
19
Publications
0
Known Names

Molecular Properties

398.4
MW (Da)
4.00
ALogP
5
HBA
1
HBD
71.3
PSA (Ų)
0.69
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H25F3N4O2
MW 398.43
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -1.75

Activity Summary

IC50 20 meas. best 9.01
Kd 1 meas. best 7.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 4
CHEMBL3524
 IC50 9.01 8.4375 1.0 4
Histone deacetylase 5
CHEMBL2563
 IC50 8.3 8.15 5.0 2
Histone deacetylase 7
CHEMBL2716
 IC50 8.0 7.945 10.0 2
Histone deacetylase 9
CHEMBL4145
 IC50 8.0 7.945 10.0 2
Unchecked
CHEMBL612545
 IC50 7.62 6.57 24.0 2
Histone deacetylase 4
CHEMBL3524
 Kd 7.36 7.36 44.0 1
Histone deacetylase 1
CHEMBL325
 IC50 5.66 5.44 2200.0 2
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 5.6 5.6 2500.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 5.54 5.54 2900.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 5.52 5.355 3000.0 2
Class 1 histone deacetylase
CHEMBL4523988
 IC50 5.52 5.52 3000.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 5.03 5.03 9300.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 834.0 mL.min-1.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 4 IC50 = 0.97 nM 9.01 Inhibition Assay: Human recombinant HDAC4 was expressed in full length form (aa ... -
Histone deacetylase 4 IC50 = 3.0 nM 8.52 Inhibition of HDAC4 (unknown origin) using Boc Lys(TFA) as substrate by fluoroge... 33738065
Histone deacetylase 4 IC50 = 3.0 nM 8.52 Inhibition of recombinant HDAC4 (unknown origin) using Boc-Lys(TFA)-AMC as subst... 36098485
Histone deacetylase 5 IC50 = 5.0 nM 8.3 Inhibition of recombinant HDAC5 (unknown origin) using Boc-Lys(TFA)-AMC as subst... 36098485
Histone deacetylase 5 IC50 = 10.0 nM 8.0 Inhibition of HDAC5 (unknown origin) using Boc Lys(TFA) as substrate by fluoroge... 33738065
Histone deacetylase 7 IC50 = 10.0 nM 8.0 Inhibition of HDAC7 (unknown origin) using Boc Lys(TFA) as substrate by fluoroge... 33738065
Histone deacetylase 9 IC50 = 10.0 nM 8.0 Inhibition of HDAC9 (unknown origin) using Boc Lys(TFA) as substrate by fluoroge... 33738065
Histone deacetylase 7 IC50 = 13.0 nM 7.89 Inhibition of recombinant HDAC7 (unknown origin) using Boc-Lys(TFA)-AMC as subst... 36098485
Histone deacetylase 9 IC50 = 13.0 nM 7.89 Inhibition of recombinant HDAC9 (unknown origin) using Boc-Lys(TFA)-AMC as subst... 36098485
Histone deacetylase 4 IC50 = 20.0 nM 7.7 Inhibition of Class 2A HDAC4 in human Jurkat E6.1 cells using Boc-Lys-(TFA)-AMC ... 33738065
Unchecked IC50 = 24.0 nM 7.62 Inhibition of class 2a HDAC in human Jurkat E6.1 cells using Boc-Lys(TFA)-AMC as... 36098485
Histone deacetylase 4 Kd = 44.0 nM 7.36 Binding affinity to immobilized HDAC4 catalytic domain (unknown origin) by surfa... 33738065
Histone deacetylase 1 IC50 = 2200.0 nM 5.66 Inhibition Assay: A similar assay procedure as described in Test 2 was used for ... -
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 2500.0 nM 5.6 Inhibition of HDAC3/NCOR2 (unknown origin) using Boc-Lys(Ac) as substrate by flu... 33738065
Histone deacetylase 8 IC50 = 2900.0 nM 5.54 Inhibition of HDAC8 (unknown origin) using Boc-Lys(TFA) as substrate by fluoroge... 33738065
Histone deacetylase 6 IC50 = 3000.0 nM 5.52 Inhibition Assay: A similar assay procedure as described in Test 2 was used for ... -
Unchecked IC50 = 3000.0 nM 5.52 Inhibition of Class 1/2b HDAC in human Jurkat E6.1 cells using Boc-Lys-(Ac)-AMC ... 33738065
Class 1 histone deacetylase IC50 = 3000.0 nM 5.52 Inhibition of class 1 HDAC in human Jurkat E6.1 cells using Boc-Lys(Ac)-AMC as s... 36098485
Histone deacetylase 1 IC50 = 6000.0 nM 5.22 Inhibition of HDAC1 (unknown origin) using Ac-Arg-Gly-Lys(Ac) as substrate by fl... 33738065
Histone deacetylase 6 IC50 = 6400.0 nM 5.19 Inhibition of HDAC6 (unknown origin) expressed in human HEK-Freestyle cells usin... 33738065

Literature References

PubMed DOI Target Context # Activities
33738065 10.1021/acsmedchemlett.0c00532 Histone deacetylase 4 4
33738065 10.1021/acsmedchemlett.0c00532 ADMET 3
33738065 10.1021/acsmedchemlett.0c00532 No relevant target 2
33738065 10.1021/acsmedchemlett.0c00532 Unchecked 2
36098485 10.1021/acs.jmedchem.2c01149 No relevant target 1
36098485 10.1021/acs.jmedchem.2c01149 Class 1 histone deacetylase 1
36098485 10.1021/acs.jmedchem.2c01149 Unchecked 1
36098485 10.1021/acs.jmedchem.2c01149 Histone deacetylase 9 1
36098485 10.1021/acs.jmedchem.2c01149 Histone deacetylase 7 1
36098485 10.1021/acs.jmedchem.2c01149 Histone deacetylase 5 1
36098485 10.1021/acs.jmedchem.2c01149 Histone deacetylase 4 1
33738065 10.1021/acsmedchemlett.0c00532 Histone deacetylase 6 1
33738065 10.1021/acsmedchemlett.0c00532 Histone deacetylase 8 1
33738065 10.1021/acsmedchemlett.0c00532 Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 1
33738065 10.1021/acsmedchemlett.0c00532 Histone deacetylase 2 1
33738065 10.1021/acsmedchemlett.0c00532 Histone deacetylase 1 1
33738065 10.1021/acsmedchemlett.0c00532 Histone deacetylase 9 1
33738065 10.1021/acsmedchemlett.0c00532 Histone deacetylase 7 1
33738065 10.1021/acsmedchemlett.0c00532 Histone deacetylase 5 1

Data from ChEMBL 36 via Core Engine