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Compound Detail

CHEMBL4554522

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COc1ccc(CN2CCC(Nc3nc(Nc4ccc(NC(=O)CCCCCCC(=O)NO)cc4)nc4cc(OC)c(OC)cc34)CC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4554522
Phase Preclinical
Structure Type MOL
InChI Key YCEGYFYGGNMXMU-UHFFFAOYSA-N
19
Targets
22
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

685.8
MW (Da)
6.26
ALogP
11
HBA
5
HBD
159.2
PSA (Ų)
0.05
QED
3
Ro5 Violations
17
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C37H47N7O6
MW 685.83
Aromatic Rings 4
Heavy Atoms 50
NP-Likeness -0.94

Activity Summary

EC50 11 meas. best 5.55
IC50 11 meas. best 8.59

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 6
CHEMBL1865
 IC50 8.59 8.59 2.6 1
Histone deacetylase 3
CHEMBL1829
 IC50 7.47 7.47 34.0 1
Plasmodium falciparum
CHEMBL364
 IC50 6.84 6.565 145.0 2
Histone deacetylase 1
CHEMBL325
 IC50 6.05 6.05 896.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 5.95 5.95 1130.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 5.9 5.9 1260.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 5.74 5.74 1810.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 5.57 5.57 2690.0 1
MOLM-14
CHEMBL3706570
 EC50 5.55 5.55 2800.0 1
NCI-H929
CHEMBL4296391
 EC50 5.34 5.34 4600.0 1
MDA-MB-231
CHEMBL400
 EC50 5.2 5.2 6300.0 1
MCF7
CHEMBL387
 EC50 5.14 5.14 7300.0 1
Histone deacetylase 1/2/3
CHEMBL3430897
 EC50 5.12 5.12 7500.0 1
KMS-12-BM
CHEMBL4296455
 EC50 5.12 5.12 7600.0 1
OPM-2
CHEMBL2366353
 EC50 5.1 5.1 7900.0 1
DNA (cytosine-5)-methyltransferase 1
CHEMBL1993
 IC50 4.85 4.85 14000.0 1
TAMH
CHEMBL4483280
 EC50 4.54 4.54 29000.0 1
DNA (cytosine-5)-methyltransferase 3A
CHEMBL1992
 IC50 4.13 4.13 74000.0 1
Unchecked
CHEMBL612545
 EC50 4.03 4.03 94000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 16.3 mL.min-1.g-1 Rattus norvegicus
CL 22.3 mL.min-1.g-1 Rattus norvegicus
CL 52.2 mL.min-1.g-1 Mus musculus
T1/2 2.385 hr Rattus norvegicus
T1/2 1.727 hr Rattus norvegicus
T1/2 0.4433 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 6 IC50 = 2.57 nM 8.59 Inhibition of human HDAC6 using Arg-His-Lys-Lys (Ac) as substrate incubated for ... 31627059
Histone deacetylase 3 IC50 = 34.0 nM 7.47 Inhibition of human HDAC3 using Arg-His-Lys-Lys (Ac) as substrate incubated for ... 31627059
Plasmodium falciparum IC50 = 145.0 nM 6.84 Antimalarial activity against ring stage Plasmodium falciparum 3D7 incubated for... 31627059
Plasmodium falciparum IC50 = 508.0 nM 6.29 Antimalarial activity against ring stage Plasmodium falciparum K1 incubated for ... 31627059
Histone deacetylase 1 IC50 = 896.0 nM 6.05 Inhibition of human HDAC1 using Arg-His-Lys-Lys (Ac) as substrate incubated for ... 31627059
Histone deacetylase 2 IC50 = 1130.0 nM 5.95 Inhibition of human HDAC2 using Arg-His-Lys-Lys (Ac) as substrate incubated for ... 31627059
Histone deacetylase 8 IC50 = 1260.0 nM 5.9 Inhibition of human HDAC8 using Arg-His-Lys (Ac)-Lys (Ac) as substrate incubated... 31627059
Histone deacetylase 11 IC50 = 1810.0 nM 5.74 Inhibition of human HDAC11 using Acetyl-Lys (trifluoroacetyl)-AMC) as substrate ... 31627059
Polyamine deacetylase HDAC10 IC50 = 2690.0 nM 5.57 Inhibition of human HDAC10 using Acetyl-Lys (trifluoroacetyl)-AMC) as substrate ... 31627059
MOLM-14 EC50 = 2800.0 nM 5.55 Antiproliferative activity against human MOLM14 cells incubated for 48 hrs by Ce... 31627059
NCI-H929 EC50 = 4600.0 nM 5.34 Antiproliferative activity against human NCI-H929 cells incubated for 48 hrs by ... 31627059
MDA-MB-231 EC50 = 6300.0 nM 5.2 Antiproliferative activity against human MDA-MB-231 cells incubated for 72 hrs b... 31627059
MCF7 EC50 = 7300.0 nM 5.14 Antiproliferative activity against human MCF7 cells incubated for 72 hrs by MTT ... 31627059
KMS-12-BM EC50 = 7600.0 nM 5.12 Antiproliferative activity against human KMS-12-BM cells incubated for 48 hrs by... 31627059
Histone deacetylase 1/2/3 EC50 = 7500.0 nM 5.12 Inhibition of HDAC1/2/3 in human KMS-12-BM cells assessed as increase in Ac-H3 l... 31627059
OPM-2 EC50 = 7900.0 nM 5.1 Antiproliferative activity against human OPM2 cells incubated for 48 hrs by Cell... 31627059
DNA (cytosine-5)-methyltransferase 1 IC50 = 14000.0 nM 4.85 Inhibition of human DNMT1 using Poly(dI-dC) as substrate incubated for 1 hr in p... 31627059
TAMH EC50 = 29000.0 nM 4.54 Cytotoxicity against TAMH cells incubated for 24 hrs by CellTiter-Glo Cell Viabi... 31627059
DNA (cytosine-5)-methyltransferase 3A IC50 = 74000.0 nM 4.13 Inhibition of human DNMT3a using lambda DNA as substrate incubated for 1 hr in p... 31627059
Unchecked EC50 = 94000.0 nM 4.03 Cytotoxicity against human AC10 cells incubated for 24 hrs by CellTiter-Glo Cell... 31627059

Literature References

PubMed DOI Target Context # Activities
31627059 10.1016/j.ejmech.2019.111755 Unchecked 18
31627059 10.1016/j.ejmech.2019.111755 MDA-MB-231 13
31627059 10.1016/j.ejmech.2019.111755 ADMET 8
31627059 10.1016/j.ejmech.2019.111755 No relevant target 4
31627059 10.1016/j.ejmech.2019.111755 KMS-12-BM 3
31627059 10.1016/j.ejmech.2019.111755 Histone deacetylase 6 2
31627059 10.1016/j.ejmech.2019.111755 Histone deacetylase 1/2/3 2
31627059 10.1016/j.ejmech.2019.111755 Plasmodium falciparum 2
31627059 10.1016/j.ejmech.2019.111755 Histone-lysine N-methyltransferase EHMT2 2
31627059 10.1016/j.ejmech.2019.111755 TAMH 1
31627059 10.1016/j.ejmech.2019.111755 Histone deacetylase 11 1
31627059 10.1016/j.ejmech.2019.111755 Polyamine deacetylase HDAC10 1
31627059 10.1016/j.ejmech.2019.111755 Histone deacetylase 1 1
31627059 10.1016/j.ejmech.2019.111755 MOLM-14 1
31627059 10.1016/j.ejmech.2019.111755 OPM-2 1
31627059 10.1016/j.ejmech.2019.111755 NCI-H929 1
31627059 10.1016/j.ejmech.2019.111755 MCF7 1
31627059 10.1016/j.ejmech.2019.111755 Histone-lysine N-methyltransferase SUV39H2 1
31627059 10.1016/j.ejmech.2019.111755 Histone-lysine N-methyltransferase SUV39H1 1
31627059 10.1016/j.ejmech.2019.111755 Histone-lysine N-methyltransferase SETD7 1

Data from ChEMBL 36 via Core Engine