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Compound Detail

CHEMBL4597954

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CCCNNC(=O)/C=C/c1ccc(CNCCc2c(C)[nH]c3ccccc23)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4597954
Phase Preclinical
Structure Type MOL
InChI Key VGRNFHJXEIFRTK-OUKQBFOZSA-N
8
Targets
13
Activities
1
Assay Types
4
PK Parameters
17
Publications
0
Known Names

Molecular Properties

390.5
MW (Da)
3.85
ALogP
3
HBA
4
HBD
69.0
PSA (Ų)
0.24
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H30N4O
MW 390.53
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.73

Activity Summary

IC50 13 meas. best 9.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 3
CHEMBL1829
 IC50 9.55 9.3567 0.3 3
Histone deacetylase 1
CHEMBL325
 IC50 8.36 8.3167 4.4 3
MV4-11
CHEMBL613835
 IC50 7.81 7.81 15.3 1
HL-60
CHEMBL383
 IC50 7.45 7.45 35.8 1
Histone deacetylase 2
CHEMBL1937
 IC50 7.4 7.35 40.0 2
RS4-11
CHEMBL2366159
 IC50 7.4 7.4 40.1 1
MOLM-13
CHEMBL3706572
 IC50 7.29 7.29 51.5 1
U-937
CHEMBL612794
 IC50 7.07 7.07 86.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 265.0 ng.hr.mL-1 Mus musculus
Cmax 115.48 nM Mus musculus
F 19.8 % Mus musculus
T1/2 7.45 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 3 IC50 = 0.28 nM 9.55 Inhibition of human recombinant HDAC3 using Boc-Lys(acetyl)-AMC substrate incuba... 34942071
Histone deacetylase 3 IC50 = 0.3 nM 9.52 Inhibition of human recombinant HDAC3 using Boc-Lys (acetyl)-AMC as flurogenic s... 39047608
Histone deacetylase 3 IC50 = 1.0 nM 9.0 Inhibition of human recombinant HDAC3 using Ac-RHKK(Acetyl)-AMC peptide as fluor... 37708798
Histone deacetylase 1 IC50 = 4.4 nM 8.36 Inhibition of human recombinant HDAC1 using Boc-Lys (acetyl)-AMC as flurogenic s... 39047608
Histone deacetylase 1 IC50 = 5.0 nM 8.3 Inhibition of human recombinant HDAC1 using Ac-RHKK(Acetyl)-AMC peptide as fluor... 37708798
Histone deacetylase 1 IC50 = 5.17 nM 8.29 Inhibition of human recombinant HDAC1 using Boc-Lys(acetyl)-AMC substrate incuba... 34942071
MV4-11 IC50 = 15.35 nM 7.81 Antiproliferative activity against human MV4-11 AML cells assessed as cell viabi... 34942071
HL-60 IC50 = 35.82 nM 7.45 Antiproliferative activity against human HL-60 cells assessed as reduction in ce... 34942071
RS4-11 IC50 = 40.06 nM 7.4 Antiproliferative activity against human RS4-11 cells assessed as reduction in c... 34942071
Histone deacetylase 2 IC50 = 40.0 nM 7.4 Inhibition of human recombinant HDAC2 using Boc-Lys (acetyl)-AMC as flurogenic s... 39047608
Histone deacetylase 2 IC50 = 49.5 nM 7.3 Inhibition of human recombinant HDAC2 using Boc-Lys(acetyl)-AMC substrate incuba... 34942071
MOLM-13 IC50 = 51.46 nM 7.29 Antiproliferative activity against human MOLM-13 cells assessed as reduction in ... 34942071
U-937 IC50 = 86.03 nM 7.07 Antiproliferative activity against human U-937 cells assessed as reduction in ce... 34942071

Literature References

PubMed DOI Target Context # Activities
34942071 10.1021/acs.jmedchem.1c01472 ADMET 4
34942071 10.1021/acs.jmedchem.1c01472 HL-60 1
39047608 10.1016/j.ejmech.2024.116663 Unchecked 1
39047608 10.1016/j.ejmech.2024.116663 Histone deacetylase 3 1
39047608 10.1016/j.ejmech.2024.116663 Histone deacetylase 2 1
39047608 10.1016/j.ejmech.2024.116663 Histone deacetylase 1 1
37708798 10.1016/j.ejmech.2023.115800 Histone deacetylase 6 1
37708798 10.1016/j.ejmech.2023.115800 Histone deacetylase 3 1
37708798 10.1016/j.ejmech.2023.115800 Histone deacetylase 1 1
34942071 10.1021/acs.jmedchem.1c01472 U-937 1
34942071 10.1021/acs.jmedchem.1c01472 Histone deacetylase 6 1
34942071 10.1021/acs.jmedchem.1c01472 RS4-11 1
34942071 10.1021/acs.jmedchem.1c01472 MOLM-13 1
34942071 10.1021/acs.jmedchem.1c01472 MV4-11 1
34942071 10.1021/acs.jmedchem.1c01472 Histone deacetylase 2 1
34942071 10.1021/acs.jmedchem.1c01472 Histone deacetylase 3 1
34942071 10.1021/acs.jmedchem.1c01472 Histone deacetylase 1 1

Data from ChEMBL 36 via Core Engine