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Compound Detail

CHEMBL5435925

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COc1ccc(-c2cc(C(=O)NCc3ccc(C(=O)NO)cc3)ccn2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5435925
Phase Preclinical
Structure Type MOL
InChI Key BOPYJZYHIIFOOS-UHFFFAOYSA-N
13
Targets
13
Activities
1
Assay Types
17
PK Parameters
20
Publications
0
Known Names

Molecular Properties

377.4
MW (Da)
2.81
ALogP
5
HBA
3
HBD
100.5
PSA (Ų)
0.45
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H19N3O4
MW 377.40
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -1.11

Activity Summary

IC50 13 meas. best 8.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 1
CHEMBL325
 IC50 8.68 8.68 2.1 1
Histone deacetylase 6
CHEMBL1865
 IC50 8.62 8.62 2.4 1
Histone deacetylase 2
CHEMBL1937
 IC50 8.33 8.33 4.7 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.97 6.97 107.0 1
MV4-11
CHEMBL613835
 IC50 6.85 6.85 140.0 1
MOLT-4
CHEMBL614177
 IC50 6.6 6.6 250.0 1
MGC-803
CHEMBL3706566
 IC50 6.35 6.35 450.0 1
THP-1
CHEMBL614245
 IC50 6.33 6.33 470.0 1
HCT-116
CHEMBL394
 IC50 6.24 6.24 570.0 1
Lysine-specific histone demethylase 1A
CHEMBL6136
 IC50 5.87 5.87 1340.0 1
A549
CHEMBL392
 IC50 5.83 5.83 1480.0 1
Histone deacetylase 5
CHEMBL2563
 IC50 5.07 5.07 8492.0 1
GES1
CHEMBL4296415
 IC50 5.06 5.06 8660.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 644.1 ng.hr.mL-1 Rattus norvegicus
AUC 645.8 ng.hr.mL-1 Rattus norvegicus
AUC 685.2 ng.hr.mL-1 Rattus norvegicus
AUC 766.2 ng.hr.mL-1 Rattus norvegicus
CL 28.88 mL.min-1.g-1 Rattus norvegicus
CL 28.8 mL.min-1.g-1 Homo sapiens
CL 1.61 mL.min-1.kg-1 Rattus norvegicus
Cmax 5015.9 nM Rattus norvegicus
Cmax 1898.25 nM Rattus norvegicus
F 10.6 % Rattus norvegicus
T1/2 2.0 hr Rattus norvegicus
T1/2 2.0 hr Homo sapiens
T1/2 0.37 hr Rattus norvegicus
T1/2 2.75 hr Rattus norvegicus
Tmax 0.25 hr Rattus norvegicus
Vd 0.82 L.kg-1 Rattus norvegicus
Vd 52.2 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 1 IC50 = 2.07 nM 8.68 Inhibition of C-terminal FLAG tagged recombinant human HDAC1 expressed in Sf9 ce... 37086699
Histone deacetylase 6 IC50 = 2.4 nM 8.62 Inhibition of C-terminal FLAG-tagged human full length recombinant HDAC6 express... 37086699
Histone deacetylase 2 IC50 = 4.71 nM 8.33 Inhibition of C-terminal 6His-tagged human recombinant HDAC2 (1 to 488 residues)... 37086699
Histone deacetylase 8 IC50 = 107.0 nM 6.97 Inhibition of C-terminal 6His-tagged human full length recombinant HDAC8 express... 37086699
MV4-11 IC50 = 140.0 nM 6.85 Antiproliferative activity against human MV4-11 cells assessed as inhibition of ... 37086699
MOLT-4 IC50 = 250.0 nM 6.6 Antiproliferative activity against human MOLT-4 cells assessed as inhibition of ... 37086699
MGC-803 IC50 = 450.0 nM 6.35 Antiproliferative activity against human MGC-803 cells assessed as inhibition of... 37086699
THP-1 IC50 = 470.0 nM 6.33 Antiproliferative activity against human THP-1 cells assessed as inhibition of c... 37086699
HCT-116 IC50 = 570.0 nM 6.24 Antiproliferative activity against human HCT-116 cells assessed as inhibition of... 37086699
Lysine-specific histone demethylase 1A IC50 = 1340.0 nM 5.87 Inhibition of recombinant LSD1 (unknown origin) using H3K4me2 as a substrate by ... 37086699
A549 IC50 = 1480.0 nM 5.83 Antiproliferative activity against human A549 cells assessed as inhibition of ce... 37086699
Histone deacetylase 5 IC50 = 8492.0 nM 5.07 Inhibition of C-terminal His-tagged human HDAC5 catalytic domain (656 to 1122 re... 37086699
GES1 IC50 = 8660.0 nM 5.06 Cytotoxicity against human GES1 cells harboring low LSD1 expression assessed as ... 37086699

Literature References

PubMed DOI Target Context # Activities
37086699 10.1016/j.ejmech.2023.115367 MGC-803 36
37086699 10.1016/j.ejmech.2023.115367 HCT-116 26
37086699 10.1016/j.ejmech.2023.115367 ADMET 24
37086699 10.1016/j.ejmech.2023.115367 Lysine-specific histone demethylase 1A 9
37086699 10.1016/j.ejmech.2023.115367 Histone deacetylase 6
37086699 10.1016/j.ejmech.2023.115367 THP-1 3
37086699 10.1016/j.ejmech.2023.115367 Histone deacetylase 1 2
37086699 10.1016/j.ejmech.2023.115367 Unchecked 2
37086699 10.1016/j.ejmech.2023.115367 GES1 1
37086699 10.1016/j.ejmech.2023.115367 Histone deacetylase 2 1
37086699 10.1016/j.ejmech.2023.115367 Histone deacetylase 5 1
37086699 10.1016/j.ejmech.2023.115367 Histone deacetylase 6 1
37086699 10.1016/j.ejmech.2023.115367 Histone deacetylase 8 1
37086699 10.1016/j.ejmech.2023.115367 Amine oxidase [flavin-containing] A 1
37086699 10.1016/j.ejmech.2023.115367 Amine oxidase [flavin-containing] B 1
37086699 10.1016/j.ejmech.2023.115367 MV4-11 1
37086699 10.1016/j.ejmech.2023.115367 MOLT-4 1
37086699 10.1016/j.ejmech.2023.115367 Cytochrome P450 1A2 1
37086699 10.1016/j.ejmech.2023.115367 Cytochrome P450 2C9 1
37086699 10.1016/j.ejmech.2023.115367 Cytochrome P450 2C19 1

Data from ChEMBL 36 via Core Engine