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Compound Detail

CHEMBL3774414

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COc1ccc(N(C)c2nc(C)nc3ccccc23)cc1OCCCC(=O)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3774414
Phase Preclinical
Structure Type MOL
InChI Key FWXZZFONXWYSEF-UHFFFAOYSA-N
27
Targets
44
Activities
2
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

396.4
MW (Da)
3.38
ALogP
7
HBA
2
HBD
96.8
PSA (Ų)
0.34
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H24N4O4
MW 396.45
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.91

Activity Summary

IC50 42 meas. best 7.85
EC50 2 meas. best 7.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.85 7.5583 14.0 6
Histone deacetylase 6
CHEMBL1865
 IC50 7.77 7.77 17.0 2
NCI-H460
CHEMBL396
 IC50 7.51 7.51 31.0 1
SK-OV-3
CHEMBL614925
 IC50 7.51 7.51 31.0 1
RPMI-8226
CHEMBL614882
 IC50 7.51 7.51 31.0 1
Ramos
CHEMBL614629
 IC50 7.51 7.33 31.0 2
A-375
CHEMBL613859
 IC50 7.51 7.43 31.0 2
MV4-11
CHEMBL613835
 IC50 7.51 7.365 31.0 2
Unchecked
CHEMBL612545
 IC50 7.51 7.51 31.0 3
MM1.S
CHEMBL4296471
 IC50 7.51 7.51 31.0 1
JeKo-1
CHEMBL4296445
 IC50 7.51 7.51 31.0 1
A2780S
CHEMBL4296398
 IC50 7.51 7.51 31.0 1
MDA-MB-231
CHEMBL400
 IC50 7.51 7.51 31.0 1
HepG2
CHEMBL395
 IC50 7.51 7.45 31.0 2
HCT-116
CHEMBL394
 IC50 7.51 7.51 31.0 1
A549
CHEMBL392
 IC50 7.51 7.245 31.0 2
MCF7
CHEMBL387
 IC50 7.51 7.51 31.0 1
K562
CHEMBL385
 IC50 7.51 7.355 31.0 2
HT-29
CHEMBL384
 IC50 7.51 7.325 31.0 2
U-266
CHEMBL2366315
 IC50 7.51 7.51 31.0 1
A2780
CHEMBL614004
 IC50 7.34 7.34 46.0 1
HeLa
CHEMBL399
 IC50 7.31 7.31 49.0 1
Histone deacetylase 6
CHEMBL1865
 EC50 7.23 7.23 58.9 1
Histone deacetylase 2
CHEMBL1937
 IC50 6.41 6.41 386.0 1
Histone deacetylase 1
CHEMBL325
 IC50 6.38 6.38 422.0 1
Histone deacetylase 3
CHEMBL1829
 IC50 6.36 6.36 439.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 5.93 5.93 1176.0 1
HeLa
CHEMBL399
 EC50 5.76 5.76 1741.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 5.47 5.47 3398.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2434.12 ng.hr.mL-1 Rattus norvegicus
AUC 1242.23 ng.hr.mL-1 Rattus norvegicus
CL 116.8 mL.min-1.kg-1 Rattus norvegicus
CL 214.62 mL.min-1.kg-1 Rattus norvegicus
Cmax 5582.04 nM Rattus norvegicus
Cmax 600.58 nM Rattus norvegicus
F 47.0 % Rattus norvegicus
T1/2 7.658 hr Rattus norvegicus
T1/2 9.62 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 14.0 nM 7.85 Cytotoxicity against human U266 cells after 72 hrs by MTT assay 26443078
NON-PROTEIN TARGET IC50 = 15.0 nM 7.82 Cytotoxicity against human RPMI8226 cells after 72 hrs by MTT assay 26443078
Histone deacetylase 6 IC50 = 17.0 nM 7.77 Inhibition of human recombinant HDAC6 using AMC labeled AC-peptide as substrate ... 26443078
Histone deacetylase 6 IC50 = 17.0 nM 7.77 Inhibition of HDAC6 (unknown origin) 34101463
NON-PROTEIN TARGET IC50 = 22.0 nM 7.66 Cytotoxicity against human SKBR3 cells after 72 hrs by MTT assay 26443078
Unchecked IC50 = 31.0 nM 7.51 Antiproliferative activity against human HBL1 cells assessed as cell growth inhi... 34101463
A-375 IC50 = 31.0 nM 7.51 Antiproliferative activity against human A-375 cells assessed as cell growth inh... 34101463
NCI-H460 IC50 = 31.0 nM 7.51 Antiproliferative activity against human NCI-H460 cells assessed as cell growth ... 34101463
A549 IC50 = 31.0 nM 7.51 Antiproliferative activity against human A549 cells assessed as cell growth inhi... 34101463
HT-29 IC50 = 31.0 nM 7.51 Antiproliferative activity against human HT-29 cells assessed as cell growth inh... 34101463
MM1.S IC50 = 31.0 nM 7.51 Antiproliferative activity against human MM1.S cells assessed as cell growth inh... 34101463
RPMI-8226 IC50 = 31.0 nM 7.51 Antiproliferative activity against human RPMI-8226 cells assessed as cell growth... 34101463
Unchecked IC50 = 31.0 nM 7.51 Antiproliferative activity against human ARD cells assessed as cell growth inhib... 34101463
U-266 IC50 = 31.0 nM 7.51 Antiproliferative activity against human U-266 cells assessed as cell growth inh... 34101463
Ramos IC50 = 31.0 nM 7.51 Antiproliferative activity against human Ramos cells assessed as cell growth inh... 34101463
MCF7 IC50 = 31.0 nM 7.51 Antiproliferative activity against human MCF7 cells assessed as cell growth inhi... 34101463
JeKo-1 IC50 = 31.0 nM 7.51 Antiproliferative activity against human JeKo-1 cells assessed as cell growth in... 34101463
Unchecked IC50 = 31.0 nM 7.51 Antiproliferative activity against human LAMA84-s cells assessed as cell growth ... 34101463
K562 IC50 = 31.0 nM 7.51 Antiproliferative activity against human K562 cells assessed as cell growth inhi... 34101463
MV4-11 IC50 = 31.0 nM 7.51 Antiproliferative activity against human MV4-11 cells assessed as cell growth in... 34101463

Literature References

PubMed DOI Target Context # Activities
26443078 10.1021/acs.jmedchem.5b01342 Rattus norvegicus 11
26443078 10.1021/acs.jmedchem.5b01342 NON-PROTEIN TARGET 8
26443078 10.1021/acs.jmedchem.5b01342 Mus musculus 7
26443078 10.1021/acs.jmedchem.5b01342 Histone deacetylase 6 4
26443078 10.1021/acs.jmedchem.5b01342 Ramos 4
34101463 10.1021/acs.jmedchem.1c00100 Unchecked 3
26443078 10.1021/acs.jmedchem.5b01342 Histone deacetylase 5 2
26443078 10.1021/acs.jmedchem.5b01342 Histone deacetylase 7 2
26443078 10.1021/acs.jmedchem.5b01342 Histone deacetylase 9 2
26443078 10.1021/acs.jmedchem.5b01342 Histone deacetylase 11 2
26443078 10.1021/acs.jmedchem.5b01342 HeLa 2
26443078 10.1021/acs.jmedchem.5b01342 MV4-11 2
26443078 10.1021/acs.jmedchem.5b01342 Unchecked 2
26443078 10.1021/acs.jmedchem.5b01342 A-375 1
26443078 10.1021/acs.jmedchem.5b01342 Histone deacetylase 2 1
26443078 10.1021/acs.jmedchem.5b01342 Histone deacetylase 3 1
34101463 10.1021/acs.jmedchem.1c00100 MV4-11 1
26443078 10.1021/acs.jmedchem.5b01342 A2780 1
26443078 10.1021/acs.jmedchem.5b01342 HepG2 1
26443078 10.1021/acs.jmedchem.5b01342 Histone deacetylase 8 1

Data from ChEMBL 36 via Core Engine