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Compound Detail

CHEMBL4798571

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CN(C)CCOc1ccc(-c2cc(=O)c3c(O)cc(OCCCCCC(=O)NO)cc3o2)cc1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4798571
Phase Preclinical
Structure Type MOL
InChI Key HDHBTUFDSFLMOP-UHFFFAOYSA-N
Parent Compound CHEMBL4804017
Active Moiety CHEMBL4804017
27
Targets
28
Activities
1
Assay Types
11
PK Parameters
20
Publications
0
Known Names

Molecular Properties

470.5
MW (Da)
3.55
ALogP
8
HBA
3
HBD
121.5
PSA (Ų)
0.21
QED
0
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H31ClN2O7
MW 506.98
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness 0.27

Activity Summary

IC50 28 meas. best 7.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 7.6 6.945 25.0 2
Histone deacetylase 6
CHEMBL1865
 IC50 7.59 7.59 25.5 1
Histone deacetylase 1
CHEMBL325
 IC50 7.44 7.44 36.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 7.23 7.23 58.5 1
Histone deacetylase 3
CHEMBL1829
 IC50 7.1 7.1 79.2 1
Histone deacetylase 11
CHEMBL3310
 IC50 6.75 6.75 179.3 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 6.61 6.61 246.5 1
SUM-159-PT
CHEMBL4483269
 IC50 6.56 6.56 277.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 6.51 6.51 306.5 1
SMMC-7721
CHEMBL613831
 IC50 6.28 6.28 530.0 1
PLC
CHEMBL613522
 IC50 6.24 6.24 582.0 1
A549
CHEMBL392
 IC50 5.97 5.97 1076.0 1
HepG2
CHEMBL395
 IC50 5.94 5.94 1158.0 1
A-375
CHEMBL613859
 IC50 5.93 5.93 1177.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.92 5.92 1201.0 1
T47D
CHEMBL614361
 IC50 5.82 5.82 1529.0 1
PC-3
CHEMBL390
 IC50 5.72 5.72 1919.0 1
4T1
CHEMBL612589
 IC50 5.7 5.7 1986.0 1
MDA-MB-231
CHEMBL400
 IC50 5.69 5.69 2050.0 1
NCI-H1581
CHEMBL1075516
 IC50 5.63 5.63 2322.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 5.6 5.6 2500.0 1
NCI-H460
CHEMBL396
 IC50 5.57 5.57 2725.0 1
Bcap37
CHEMBL613842
 IC50 5.48 5.48 3278.0 1
Bel-7402
CHEMBL614279
 IC50 5.48 5.48 3312.0 1
MDA-MB-468
CHEMBL614335
 IC50 5.47 5.47 3397.0 1
BT-549
CHEMBL614072
 IC50 5.38 5.38 4130.0 1
MCF7
CHEMBL387
 IC50 5.33 5.33 4697.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1641.0 ng.hr.mL-1 Rattus norvegicus
AUC 2837.0 ng.hr.mL-1 Rattus norvegicus
Cmax 2716.14 nM Rattus norvegicus
Cmax 4639.55 nM Rattus norvegicus
F 57.8 % Rattus norvegicus
MRT 1.097 hr Rattus norvegicus
MRT 1.249 hr Rattus norvegicus
T1/2 0.249 hr Rattus norvegicus
T1/2 1.422 hr Rattus norvegicus
Tmax 0.333 hr Rattus norvegicus
Tmax 0.083 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 25.0 nM 7.6 Inhibition of HDAC in human HeLa cell extracts assessed as inhibition of substra... 32823005
Histone deacetylase 6 IC50 = 25.46 nM 7.59 Inhibition of recombinant human N-terminal GST-tagged full length HDAC-6 express... 32823005
Histone deacetylase 1 IC50 = 35.95 nM 7.44 Inhibition of recombinant human C-terminal GST-tagged full length HDAC-1 express... 32823005
Histone deacetylase 2 IC50 = 58.46 nM 7.23 Inhibition of recombinant human C-terminal GST-tagged full length HDAC-2 express... 32823005
Histone deacetylase 3 IC50 = 79.21 nM 7.1 Inhibition of recombinant human C-terminal GST-tagged full length HDAC-3 express... 32823005
Histone deacetylase 11 IC50 = 179.35 nM 6.75 Inhibition of recombinant human N-terminal GST-tagged full length HDAC-11 expres... 32823005
Polyamine deacetylase HDAC10 IC50 = 246.53 nM 6.61 Inhibition of recombinant human N-terminal GST-tagged HDAC-10 (1 to 482 residues... 32823005
SUM-159-PT IC50 = 277.0 nM 6.56 Cytotoxicity against human SUM159PT cells assessed as reduction in cell viabilit... 32823005
Histone deacetylase 4 IC50 = 306.53 nM 6.51 Inhibition of recombinant human N-terminal GST-tagged HDAC-4 (612 to end residue... 32823005
Unchecked IC50 = 510.0 nM 6.29 Cytotoxicity against human B16-F10 cells assessed as reduction in cell viability... 32823005
SMMC-7721 IC50 = 530.0 nM 6.28 Cytotoxicity against human SMMC-7721 cells assessed as reduction in cell viabili... 32823005
PLC IC50 = 582.0 nM 6.24 Cytotoxicity against human PLC cells assessed as reduction in cell viability inc... 32823005
A549 IC50 = 1076.0 nM 5.97 Cytotoxicity against human A549 cells assessed as reduction in cell viability in... 32823005
HepG2 IC50 = 1158.0 nM 5.94 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability i... 32823005
A-375 IC50 = 1177.0 nM 5.93 Cytotoxicity against human A-375 cells assessed as reduction in cell viability i... 32823005
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 1201.0 nM 5.92 Inhibition of human ERG 32823005
T47D IC50 = 1529.0 nM 5.82 Cytotoxicity against human T47D cells assessed as reduction in cell viability in... 32823005
PC-3 IC50 = 1919.0 nM 5.72 Cytotoxicity against human PC-3 cells assessed as reduction in cell viability in... 32823005
4T1 IC50 = 1986.0 nM 5.7 Cytotoxicity against mouse 4T1 cells assessed as reduction in cell viability inc... 32823005
MDA-MB-231 IC50 = 2050.0 nM 5.69 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 32823005

Literature References

PubMed DOI Target Context # Activities
32823005 10.1016/j.ejmech.2020.112677 MDA-MB-231 30
32823005 10.1016/j.ejmech.2020.112677 4T1 25
32823005 10.1016/j.ejmech.2020.112677 ADMET 22
32823005 10.1016/j.ejmech.2020.112677 Unchecked 10
32823005 10.1016/j.ejmech.2020.112677 MCF7 2
32823005 10.1016/j.ejmech.2020.112677 BT-549 2
32823005 10.1016/j.ejmech.2020.112677 MDA-MB-468 2
32823005 10.1016/j.ejmech.2020.112677 Histone deacetylase 5 2
32823005 10.1016/j.ejmech.2020.112677 Histone deacetylase 7 2
32823005 10.1016/j.ejmech.2020.112677 Histone deacetylase 9 2
32823005 10.1016/j.ejmech.2020.112677 Histone deacetylase 8 1
32823005 10.1016/j.ejmech.2020.112677 Voltage-gated inwardly rectifying potassium channel KCNH2 1
32823005 10.1016/j.ejmech.2020.112677 SUM-159-PT 1
32823005 10.1016/j.ejmech.2020.112677 Histone deacetylase 11 1
32823005 10.1016/j.ejmech.2020.112677 Polyamine deacetylase HDAC10 1
32823005 10.1016/j.ejmech.2020.112677 Histone deacetylase 6 1
32823005 10.1016/j.ejmech.2020.112677 Histone deacetylase 4 1
32823005 10.1016/j.ejmech.2020.112677 Histone deacetylase 3 1
32823005 10.1016/j.ejmech.2020.112677 Histone deacetylase 2 1
32823005 10.1016/j.ejmech.2020.112677 Histone deacetylase 1 1

Data from ChEMBL 36 via Core Engine