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Compound Detail

CHEMBL4517151

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Cc1ccc(CN2CCC(c3noc(CN(C)c4ncc(C(=O)NO)cn4)n3)CC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4517151
Phase Preclinical
Structure Type MOL
InChI Key DSDPQMCYEOZWTA-UHFFFAOYSA-N
23
Targets
23
Activities
1
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

437.5
MW (Da)
2.30
ALogP
9
HBA
2
HBD
120.5
PSA (Ų)
0.42
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H27N7O3
MW 437.50
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.92

Activity Summary

IC50 23 meas. best 8.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 1
CHEMBL325
 IC50 8.74 8.74 1.8 1
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 8.52 8.52 3.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 8.44 8.44 3.6 1
JeKo-1
CHEMBL4296445
 IC50 8.14 8.14 7.2 1
MM1.S
CHEMBL4296471
 IC50 8.01 8.01 9.8 1
Raji
CHEMBL614628
 IC50 7.92 7.92 12.1 1
HepG2
CHEMBL395
 IC50 7.89 7.89 13.0 1
MCF7
CHEMBL387
 IC50 7.84 7.84 14.4 1
RPMI-8226
CHEMBL614882
 IC50 7.81 7.81 15.6 1
HCT-116
CHEMBL394
 IC50 7.8 7.8 16.0 1
Ramos
CHEMBL614629
 IC50 7.75 7.75 17.8 1
SK-OV-3
CHEMBL614925
 IC50 7.69 7.69 20.5 1
Leukemia cell
CHEMBL614844
 IC50 7.67 7.67 21.2 1
MDA-MB-231
CHEMBL400
 IC50 7.59 7.59 25.6 1
A2780S
CHEMBL4296398
 IC50 7.4 7.4 40.0 1
Unchecked
CHEMBL612545
 IC50 7.35 7.35 44.9 1
Histone deacetylase 6
CHEMBL1865
 IC50 7.25 7.25 56.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 6.99 6.99 102.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.58 6.58 260.0 1
Histone deacetylase 7
CHEMBL2716
 IC50 6.41 6.41 392.0 1
Histone deacetylase 9
CHEMBL4145
 IC50 6.36 6.36 441.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 6.33 6.33 473.0 1
Histone deacetylase 5
CHEMBL2563
 IC50 6.27 6.27 540.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 433.26 ng.hr.mL-1 Rattus norvegicus
AUC 231.89 ng.hr.mL-1 Rattus norvegicus
CL 197.83 mL.min-1.kg-1 Rattus norvegicus
CL 371.83 mL.min-1.kg-1 Rattus norvegicus
Cmax 2182.63 nM Rattus norvegicus
Cmax 550.86 nM Rattus norvegicus
F 53.52 % Rattus norvegicus
T1/2 0.39 hr Rattus norvegicus
T1/2 1.01 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 1 IC50 = 1.8 nM 8.74 Inhibition of recombinant full length HDAC1 (unknown origin) using Ac-peptide-AM... 31177073
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 3.0 nM 8.52 Inhibition of human recombinant full length C-terminal His-tagged HDAC3 (1 to 42... 31177073
Histone deacetylase 2 IC50 = 3.6 nM 8.44 Inhibition of recombinant full length human HDAC2 expressed in sf9 insect cells ... 31177073
JeKo-1 IC50 = 7.2 nM 8.14 Antiproliferative activity against human JeKo1 cells after 72 hrs by MTT assay 31177073
MM1.S IC50 = 9.8 nM 8.01 Antiproliferative activity against human MM1S cells after 72 hrs by MTT assay 31177073
Raji IC50 = 12.1 nM 7.92 Antiproliferative activity against human Raji cells after 72 hrs by MTT assay 31177073
HepG2 IC50 = 13.0 nM 7.89 Antiproliferative activity against human HepG2 cells after 72 hrs by MTT assay 31177073
MCF7 IC50 = 14.4 nM 7.84 Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay 31177073
RPMI-8226 IC50 = 15.6 nM 7.81 Antiproliferative activity against human RPMI8226 cells after 72 hrs by MTT assa... 31177073
HCT-116 IC50 = 16.0 nM 7.8 Antiproliferative activity against human HCT116 cells after 72 hrs by MTT assay 31177073
Ramos IC50 = 17.8 nM 7.75 Antiproliferative activity against human Ramos cells after 72 hrs by MTT assay 31177073
SK-OV-3 IC50 = 20.5 nM 7.69 Antiproliferative activity against human SKOV3 cells after 72 hrs by MTT assay 31177073
Leukemia cell IC50 = 21.2 nM 7.67 Antiproliferative activity against human AML patient derived primary leukemia ce... 31177073
MDA-MB-231 IC50 = 25.6 nM 7.59 Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT as... 31177073
A2780S IC50 = 40.0 nM 7.4 Antiproliferative activity against human A2780S cells after 72 hrs by MTT assay 31177073
Unchecked IC50 = 44.9 nM 7.35 Antiproliferative activity against human ARD cells after 72 hrs by MTT assay 31177073
Histone deacetylase 6 IC50 = 56.0 nM 7.25 Inhibition of recombinant full length HDAC6 (unknown origin) using Ac-peptide-AM... 31177073
Polyamine deacetylase HDAC10 IC50 = 102.0 nM 6.99 Inhibition of recombinant N-terminal FLAG-tagged human HDAC10 (2 to 631 residues... 31177073
Histone deacetylase 8 IC50 = 260.0 nM 6.58 Inhibition of recombinant full length C-terminal His-tagged human HDAC8 expresse... 31177073
Histone deacetylase 7 IC50 = 392.0 nM 6.41 Inhibition of recombinant N-terminal GST-tagged human HDAC7 (518 to end residues... 31177073

Literature References

PubMed DOI Target Context # Activities
31177073 10.1016/j.ejmech.2019.05.089 JeKo-1 24
31177073 10.1016/j.ejmech.2019.05.089 ADMET 17
31177073 10.1016/j.ejmech.2019.05.089 Daudi 6
31177073 10.1016/j.ejmech.2019.05.089 Histone deacetylase 6 3
31177073 10.1016/j.ejmech.2019.05.089 Histone deacetylase 1 2
31177073 10.1016/j.ejmech.2019.05.089 Histone deacetylase 1/2/3 2
31177073 10.1016/j.ejmech.2019.05.089 A2780S 1
31177073 10.1016/j.ejmech.2019.05.089 MM1.S 1
31177073 10.1016/j.ejmech.2019.05.089 Unchecked 1
31177073 10.1016/j.ejmech.2019.05.089 Histone deacetylase 2 1
31177073 10.1016/j.ejmech.2019.05.089 MDA-MB-231 1
31177073 10.1016/j.ejmech.2019.05.089 MCF7 1
31177073 10.1016/j.ejmech.2019.05.089 SK-OV-3 1
31177073 10.1016/j.ejmech.2019.05.089 Histone deacetylase 8 1
31177073 10.1016/j.ejmech.2019.05.089 HCT-116 1
31177073 10.1016/j.ejmech.2019.05.089 Histone deacetylase 11 1
31177073 10.1016/j.ejmech.2019.05.089 Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 1
31177073 10.1016/j.ejmech.2019.05.089 Histone deacetylase 9 1
31177073 10.1016/j.ejmech.2019.05.089 Histone deacetylase 7 1
31177073 10.1016/j.ejmech.2019.05.089 Histone deacetylase 5 1

Data from ChEMBL 36 via Core Engine