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Compound Detail

CHEMBL4526892

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CCCNNC(=O)c1ccc(CNC(=O)/C=C/c2ccccc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4526892
Phase Preclinical
Structure Type MOL
InChI Key MHZUZIALEUTHIU-JLHYYAGUSA-N
11
Targets
34
Activities
3
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

337.4
MW (Da)
2.66
ALogP
3
HBA
3
HBD
70.2
PSA (Ų)
0.39
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H23N3O2
MW 337.42
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.92

Activity Summary

IC50 27 meas. best 9.02
EC50 4 meas. best 7.44
Ki 3 meas. best 7.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 3
CHEMBL1829
 IC50 9.02 8.4925 0.9 4
Histone deacetylase 1
CHEMBL325
 IC50 8.31 7.9486 4.9 7
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 8.22 8.1025 6.0 4
Histone deacetylase 2
CHEMBL1937
 IC50 7.85 7.27 14.0 7
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 Ki 7.6 7.6 25.0 1
MV4-11
CHEMBL613835
 EC50 7.44 7.44 36.4 1
MV4-11
CHEMBL613835
 IC50 7.44 7.44 36.4 1
Histone deacetylase 1
CHEMBL325
 Ki 7.4 7.4 40.0 1
HL-60
CHEMBL383
 IC50 7.29 7.29 51.7 1
MOLM-14
CHEMBL3706570
 EC50 7.12 7.12 76.6 1
RS4-11
CHEMBL2366159
 IC50 7.09 7.09 82.0 1
Histone deacetylase 2
CHEMBL1937
 Ki 6.99 6.99 103.0 1
MOLM-13
CHEMBL3706572
 IC50 6.99 6.99 102.7 1
RS4-11
CHEMBL2366159
 EC50 6.82 6.82 151.7 1
U-937
CHEMBL612794
 IC50 6.79 6.79 161.4 1
K562
CHEMBL385
 EC50 5.67 5.67 2160.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 3.667 hr Homo sapiens
T1/2 2.167 hr Homo sapiens
T1/2 16666.67 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 3 IC50 = 0.95 nM 9.02 Allosteric inhibition of C-terminal His-tagged recombinant human HDAC3 expressed... 27754681
Histone deacetylase 3 IC50 = 0.95 nM 9.02 Inhibition of human recombinant HDAC3 using Boc-Lys(acetyl)-AMC substrate incuba... 34942071
Histone deacetylase 3 IC50 = 0.95 nM 9.02 Inhibition Assay: Recombinant HDACs 1, 2, and 3 (BPS Biosciences) were diluted t... -
Histone deacetylase 1 IC50 = 4.89 nM 8.31 Inhibition of full length C-terminal His-tagged HDAC1 (unknown origin) using (Ac... 35586419
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 5.96 nM 8.22 Inhibition of full length C-terminal His-tagged HDAC3 (unknown origin)/N-termina... 35586419
Histone deacetylase 1 IC50 = 7.07 nM 8.15 Inhibition of full length C-terminal His-tagged HDAC1 (unknown origin) using (Ac... 35586419
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 7.84 nM 8.11 Inhibition of full length C-terminal His-tagged HDAC3 (unknown origin)/N-termina... 35586419
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 8.2 nM 8.09 Inhibition of full length C-terminal His-tagged HDAC3 (unknown origin)/N-termina... 35586419
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 10.2 nM 7.99 Inhibition of full length C-terminal His-tagged HDAC3 (unknown origin)/N-termina... 35586419
Histone deacetylase 1 IC50 = 11.3 nM 7.95 Inhibition of full length C-terminal His-tagged HDAC1 (unknown origin) using (Ac... 35586419
Histone deacetylase 1 IC50 = 11.8 nM 7.93 Inhibition Assay: Recombinant HDACs 1, 2, and 3 (BPS Biosciences) were diluted t... -
Histone deacetylase 1 IC50 = 11.81 nM 7.93 Inhibition of human recombinant HDAC1 using Boc-Lys(acetyl)-AMC substrate incuba... 34942071
Histone deacetylase 1 IC50 = 11.81 nM 7.93 Inhibition of C-terminal His-tagged recombinant human HDAC1 expressed in Sf9 cel... 27754681
Histone deacetylase 2 IC50 = 14.0 nM 7.85 Inhibition of full length C-terminal FLAG-tagged HDAC2 (unknown origin) using (A... 35586419
Histone deacetylase 2 IC50 = 24.8 nM 7.61 Inhibition of full length C-terminal FLAG-tagged HDAC2 (unknown origin) using (A... 35586419
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) Ki = 25.0 nM 7.6 Inhibition of full length C-terminal His-tagged HDAC3 (unknown origin)/N-termina... 35586419
MV4-11 IC50 = 36.37 nM 7.44 Antiproliferative activity against human MV4-11 AML cells assessed as cell viabi... 34942071
Histone deacetylase 1 IC50 = 36.4 nM 7.44 Inhibition of full length C-terminal His-tagged HDAC1 (unknown origin) using (Ac... 35586419
MV4-11 EC50 = 36.37 nM 7.44 Cytotoxicity against human MV4-11 cells assessed as reduction in cell viability ... 27754681
Histone deacetylase 1 Ki = 40.0 nM 7.4 Inhibition of full length C-terminal His-tagged HDAC1 (unknown origin) assessed ... 35586419

Literature References

PubMed DOI Target Context # Activities
35586419 10.1021/acsmedchemlett.1c00702 Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 10
35586419 10.1021/acsmedchemlett.1c00702 Histone deacetylase 1 8
35586419 10.1021/acsmedchemlett.1c00702 Histone deacetylase 2 8
27754681 10.1021/acs.jmedchem.6b01385 Histone deacetylase 3 4
27754681 10.1021/acs.jmedchem.6b01385 Unchecked 4
38224650 10.1016/j.ejmech.2024.116127 HL-60 4
35586419 10.1021/acsmedchemlett.1c00702 Unchecked 4
38224650 10.1016/j.ejmech.2024.116127 Unchecked 4
27754681 10.1021/acs.jmedchem.6b01385 Class 1 histone deacetylase 4
32321249 10.1021/acs.jmedchem.0c00442 MV4-11 3
27754681 10.1021/acs.jmedchem.6b01385 ADMET 3
34942071 10.1021/acs.jmedchem.1c01472 Unchecked 2
38224650 10.1016/j.ejmech.2024.116127 NB-4 2
38224650 10.1016/j.ejmech.2024.116127 MV4-11 2
38224650 10.1016/j.ejmech.2024.116127 Kasumi 1 2
27754681 10.1021/acs.jmedchem.6b01385 Histone deacetylase 6 1
27754681 10.1021/acs.jmedchem.6b01385 RPMI-8226 1
27754681 10.1021/acs.jmedchem.6b01385 HL-60 1
27754681 10.1021/acs.jmedchem.6b01385 RS4-11 1
27754681 10.1021/acs.jmedchem.6b01385 MOLM-14 1

Data from ChEMBL 36 via Core Engine