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Compound Detail

CHEMBL4088737

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CC(C)c1cc(C(=O)N2CC[C@@H](NC(=O)C3CC3)C2)[nH]n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4088737
Phase Preclinical
Structure Type MOL
InChI Key CXEXTVGTDZRKJS-LLVKDONJSA-N
6
Targets
16
Activities
3
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

290.4
MW (Da)
1.27
ALogP
3
HBA
2
HBD
78.1
PSA (Ų)
0.88
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H22N4O2
MW 290.37
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness -2.19

Activity Summary

IC50 12 meas. best 10.31
EC50 3 meas. best 6.02
Kd 1 meas. best 5.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Lysine-specific demethylase 5A
CHEMBL2424504
 IC50 10.31 6.9217 0.0 6
Lysine-specific demethylase 5C
CHEMBL2163176
 IC50 7.26 7.225 55.0 2
Lysine-specific demethylase 5B
CHEMBL3774295
 IC50 7.25 7.24 56.0 3
Lysine-specific demethylase 5A
CHEMBL2424504
 EC50 6.02 6.02 960.0 1
PC-9
CHEMBL614102
 EC50 5.8 5.8 1600.0 1
Lysine-specific demethylase 5A
CHEMBL2424504
 Kd 5.62 5.62 2400.0 1
Lysine-specific demethylase 4C
CHEMBL6175
 IC50 5.39 5.39 4100.0 1
BT-474
CHEMBL614529
 EC50 5.33 5.33 4700.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 28.0 mL.min-1.kg-1 Mus musculus
CL 4.2 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
CL 12.0 mL.min-1.kg-1 Mus musculus
CL 1.2 mL.min-1.kg-1 Homo sapiens
CL 6.3 mL.min-1.kg-1 Rattus norvegicus
CL 0.6 mL.min-1.kg-1 Mus musculus
F 34.0 % Mus musculus
T1/2 0.4 hr Mus musculus
Vd 0.7 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Lysine-specific demethylase 5A IC50 = 0.049 nM 10.31 KDM5 Enzyme Assay: Full length KDM5A enzyme was expressed and purified inhouse. ... -
Lysine-specific demethylase 5A IC50 = 45.0 nM 7.35 Inhibition of recombinant human N-terminal FLAG-tagged KDM5A expressed in baculo... 28512031
Lysine-specific demethylase 5A IC50 = 45.0 nM 7.35 Inhibition of KDM5A (unknown origin ) by Alphascreen assay 34555614
Lysine-specific demethylase 5C IC50 = 55.0 nM 7.26 Inhibition of recombinant human N-terminal FLAG-tagged KDM5C expressed in baculo... 28512031
Lysine-specific demethylase 5B IC50 = 56.0 nM 7.25 Inhibition of recombinant human N-terminal FLAG-tagged KDM5B expressed in baculo... 28512031
Lysine-specific demethylase 5B IC50 = 56.0 nM 7.25 Inhibition of KDM5B (unknown origin ) by TR-FRET assay 34555614
Lysine-specific demethylase 5B IC50 = 60.0 nM 7.22 Inhibition of KDM5B (unknown origin) incubated for 30 mins by HRTF assay 36112701
Lysine-specific demethylase 5C IC50 = 65.0 nM 7.19 Inhibition of KDM5C (unknown origin ) by TR-FRET assay 34555614
Lysine-specific demethylase 5A IC50 = 570.0 nM 6.24 Inhibition of recombinant human C-terminal FLAG-tagged KDM5A (1 to 1090 residues... 29537847
Lysine-specific demethylase 5A EC50 = 960.0 nM 6.02 Inhibition of KDM5A in human PC9 cells assessed as increase in H3K4me3 level aft... 28512031
PC-9 EC50 = 1600.0 nM 5.8 Antiproliferative activity against human PC-9 cells assessed as reduction in cel... 34555614
Lysine-specific demethylase 5A IC50 = 2400.0 nM 5.62 Inhibition of ARID/PHD1 domain truncated human N-terminal His-SUMO-tagged KDM5A ... 29537847
Lysine-specific demethylase 5A Kd = 2400.0 nM 5.62 Binding affinity to ARID/PHD1/Zn binding domain truncated human N-terminal His-S... 29537847
Lysine-specific demethylase 4C IC50 = 4100.0 nM 5.39 Inhibition of recombinant human N-terminal FLAG-tagged KDM4C expressed in baculo... 28512031
BT-474 EC50 = 4700.0 nM 5.33 Growth inhibition of human BT474 cells measured every 4 hrs for 288 hrs by live ... 29537847
Lysine-specific demethylase 5A IC50 = 22000.0 nM 4.66 Inhibition of ARID/PHD1 domain truncated human N-terminal His-SUMO-tagged KDM5A ... 29537847

Literature References

PubMed DOI Target Context # Activities
29537847 10.1021/acs.jmedchem.8b00261 Lysine-specific demethylase 5A 9
29537847 10.1021/acs.jmedchem.8b00261 Unchecked 7
28512031 10.1016/j.bmcl.2017.05.016 Mus musculus 4
28512031 10.1016/j.bmcl.2017.05.016 ADMET 3
28512031 10.1016/j.bmcl.2017.05.016 Liver 3
28512031 10.1016/j.bmcl.2017.05.016 Plasma 3
36112701 10.1021/acs.jmedchem.2c00797 Lysine-specific demethylase 5B 2
28512031 10.1016/j.bmcl.2017.05.016 Unchecked 2
28512031 10.1016/j.bmcl.2017.05.016 No relevant target 2
28512031 10.1016/j.bmcl.2017.05.016 Lysine-specific demethylase 5A 2
29537847 10.1021/acs.jmedchem.8b00261 MCF7 2
28512031 10.1016/j.bmcl.2017.05.016 Lysine-specific demethylase 3B 1
28512031 10.1016/j.bmcl.2017.05.016 Lysine-specific demethylase 4C 1
28512031 10.1016/j.bmcl.2017.05.016 Lysine-specific demethylase 6A 1
28512031 10.1016/j.bmcl.2017.05.016 Histone lysine demethylase PHF8 1
28512031 10.1016/j.bmcl.2017.05.016 Lysine-specific demethylase 2B 1
28512031 10.1016/j.bmcl.2017.05.016 Lysine-specific histone demethylase 1A 1
29537847 10.1021/acs.jmedchem.8b00261 MDA-MB-231 1
29537847 10.1021/acs.jmedchem.8b00261 SK-BR-3 1
29537847 10.1021/acs.jmedchem.8b00261 BT-474 1

Data from ChEMBL 36 via Core Engine