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Compound Detail

CHEMBL4454253

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CC(C)c1c(-c2ccccc2)[nH]c2c(C#N)cnn2c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4454253
Phase Preclinical
Structure Type MOL
InChI Key DHXKRMSKXLDZGY-UHFFFAOYSA-N
16
Targets
33
Activities
2
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

278.3
MW (Da)
2.68
ALogP
4
HBA
1
HBD
74.0
PSA (Ų)
0.78
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H14N4O
MW 278.31
Aromatic Rings 3
Heavy Atoms 21
NP-Likeness -1.02

Activity Summary

IC50 31 meas. best 8.52
EC50 2 meas. best 5.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Lysine-specific demethylase 5B
CHEMBL3774295
 IC50 8.52 8.101 3.0 10
Lysine-specific demethylase 5A
CHEMBL2424504
 IC50 8.0 7.6 10.0 5
Unchecked
CHEMBL612545
 IC50 8.0 8.0 10.0 1
Lysine-specific demethylase 5C
CHEMBL2163176
 IC50 7.85 7.0733 14.0 3
Lysine-specific demethylase 4C
CHEMBL6175
 IC50 5.7 5.7 2000.0 1
Lysine-specific demethylase 5D
CHEMBL5169191
 IC50 5.7 5.7 2000.0 1
Lysine-specific demethylase 5A
CHEMBL2424504
 EC50 5.28 5.28 5200.0 1
PC-9
CHEMBL614102
 EC50 5.28 5.28 5200.0 1
Histone lysine demethylase PHF8
CHEMBL1938212
 IC50 5.11 5.11 7700.0 1
Lysine-specific demethylase 6B
CHEMBL1938211
 IC50 4.84 4.84 14300.0 1
MKN-45
CHEMBL614354
 IC50 4.62 4.57 23790.0 2
PC-3
CHEMBL390
 IC50 4.57 4.57 26710.0 1
LNCaP
CHEMBL612518
 IC50 4.53 4.53 29640.0 1
MGC-803
CHEMBL3706566
 IC50 4.47 4.47 33720.0 1
MCF7
CHEMBL387
 IC50 4.45 4.45 35430.0 1
DU-145
CHEMBL613508
 IC50 4.45 4.45 35900.0 1
HepG2
CHEMBL395
 IC50 4.37 4.37 42650.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3701.52 ng.hr.mL-1 Mus musculus
AUC 17477.87 ng.hr.mL-1 Mus musculus
CL 24.0 mL.min-1.kg-1 Mus musculus
CL 7.0 mL.min-1.kg-1 Rattus norvegicus
CL 6.0 mL.min-1.kg-1 Homo sapiens
CL 4.4 mL.min-1.kg-1 Mus musculus
CL 4.4 mL.min-1.kg-1 Mus musculus
Cmax 192000.0 nM Mus musculus
F 100.0 % Mus musculus
F 100.0 % Mus musculus
T1/2 1.18 hr Mus musculus
T1/2 3.4 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Lysine-specific demethylase 5B IC50 = 3.0 nM 8.52 Inhibition of KDM5B (unknown origin) using ART(Kme3)QTARKSTGGKAPRKQLA-NovaTagPEG... 27476424
Lysine-specific demethylase 5B IC50 = 3.0 nM 8.52 Inhibition of full length human KDM5B expressed in baculovirus expression system... 36112701
Lysine-specific demethylase 5B IC50 = 3.0 nM 8.52 Inhibition of KDM5B (unknown origin) 32883639
Lysine-specific demethylase 5B IC50 = 3.0 nM 8.52 Inhibition of KDM5B (unknown origin ) by HTMS analysis 34555614
Lysine-specific demethylase 5B IC50 = 3.0 nM 8.52 Inhibition of human full length KDM5B using ART(Kme3)QTARKSTGGKAPRKQLANovaTagPEG... 38749268
Lysine-specific demethylase 5A IC50 = 10.0 nM 8.0 Inhibition of KDM5A (unknown origin) using ART(Kme3)QTARKSTGGKAPRKQLA-NovaTagPEG... 27476424
Unchecked IC50 = 10.0 nM 8.0 Competitive inhibition of KDM5 (unknown origin) in presence of 2-OG 27499454
Lysine-specific demethylase 5B IC50 = 10.0 nM 8.0 Inhibition of KDM5B (unknown origin) 30343192
Lysine-specific demethylase 5A IC50 = 10.0 nM 8.0 Inhibition of KDM5A (unknown origin) using H3K4me3 as substrate by MSD ELISA ana... 34591474
Lysine-specific demethylase 5A IC50 = 10.0 nM 8.0 Inhibition of KDM5A (unknown origin ) by HTMS analysis 34555614
Lysine-specific demethylase 5B IC50 = 10.0 nM 8.0 Inhibition of KDM5B (unknown origin) 38214982
Lysine-specific demethylase 5B IC50 = 10.52 nM 7.98 Inhibition of recombinant human N-terminal FLAG-tagged KDM5B expressed in Sf9 in... 32155529
Lysine-specific demethylase 5B IC50 = 11.0 nM 7.96 Inhibition of KDM5B (unknown origin) 36931124
Lysine-specific demethylase 5C IC50 = 14.0 nM 7.85 Inhibition of KDM5C (unknown origin ) by HTMS assay 34555614
Lysine-specific demethylase 5C IC50 = 14.0 nM 7.85 Inhibition of KDM5C (unknown origin) using ART(Kme3)QTARKSTGGKAPRKQLA-NovaTagPEG... 27476424
Lysine-specific demethylase 5A IC50 = 20.0 nM 7.7 Inhibition of KDM5A (unknown origin) using ART(Kme3)QTARKSTGGKAPRKQLA-NovaTagPEG... 27476424
Lysine-specific demethylase 5B IC50 = 337.0 nM 6.47 Inhibition of human N-terminal FLAG/His-tagged KDM5B (2 to 751 residues) express... 30745098
Lysine-specific demethylase 5A IC50 = 506.0 nM 6.3 Inhibition of human C-terminal FLAG-tagged KDM5A (1 to 1090 residues) expressed ... 30745098
Lysine-specific demethylase 4C IC50 = 2000.0 nM 5.7 Inhibition of KDM4C (unknown origin) using ARTKQTAR(KMe3)STGGKAPRKQLA-NovaTagPEG... 27476424
Lysine-specific demethylase 5D IC50 = 2000.0 nM 5.7 Inhibition of KDM5D (unknown origin ) by HTMS assay 34555614

Literature References

PubMed DOI Target Context # Activities
27476424 10.1016/j.bmcl.2016.07.026 ADMET 17
27476424 10.1016/j.bmcl.2016.07.026 Unchecked 7
36931124 10.1016/j.ejmech.2023.115250 Unchecked 4
32155529 10.1016/j.ejmech.2020.112161 MKN-45 4
27476424 10.1016/j.bmcl.2016.07.026 Lysine-specific demethylase 5A 4
34555614 10.1016/j.ejmech.2021.113855 ADMET 4
30745098 10.1016/j.bmc.2019.02.006 Lysine-specific demethylase 5A 4
30745098 10.1016/j.bmc.2019.02.006 Lysine-specific demethylase 6B 3
38294854 10.1021/acs.jmedchem.3c01820 Methylcytosine dioxygenase TET1 3
30745098 10.1016/j.bmc.2019.02.006 Histone lysine demethylase PHF8 2
30745098 10.1016/j.bmc.2019.02.006 A549 2
30745098 10.1016/j.bmc.2019.02.006 Lysine-specific demethylase 4A 2
38749268 10.1016/j.ejmech.2024.116494 Lysine-specific demethylase 5B 2
38294854 10.1021/acs.jmedchem.3c01820 Unchecked 2
38294854 10.1021/acs.jmedchem.3c01820 Methylcytosine dioxygenase TET2 2
30745098 10.1016/j.bmc.2019.02.006 Lysine-specific demethylase 3A 2
27476424 10.1016/j.bmcl.2016.07.026 Lysine-specific demethylase 5C 2
27476424 10.1016/j.bmcl.2016.07.026 Lysine-specific demethylase 5B 2
30745098 10.1016/j.bmc.2019.02.006 Lysine-specific demethylase 2A 2
38294854 10.1021/acs.jmedchem.3c01820 Methylcytosine dioxygenase TET3 2

Data from ChEMBL 36 via Core Engine