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Compound Detail

CHEMBL3188597

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O=C(O)CCNc1cc(N2CCc3ccccc3CC2)nc(-c2ccccn2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3188597
Phase Preclinical
Structure Type MOL
InChI Key AVZCPICCWKMZDT-UHFFFAOYSA-N
19
Targets
43
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

389.5
MW (Da)
3.03
ALogP
6
HBA
2
HBD
91.2
PSA (Ų)
0.67
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C22H23N5O2
MW 389.46
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -1.39

Activity Summary

IC50 42 meas. best 7.8
Kd 1 meas. best 4.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Lysine-specific demethylase 6B
CHEMBL1938211
 IC50 7.8 6.7183 16.0 12
Lysine-specific demethylase 6A
CHEMBL2069164
 IC50 7.28 5.23 53.0 3
Histone-lysine N-methyltransferase EZH2
CHEMBL2189110
 IC50 7.22 7.22 60.0 1
Lysine-specific demethylase 5B
CHEMBL3774295
 IC50 6.77 6.37 170.0 5
Lysine-specific demethylase 5C
CHEMBL2163176
 IC50 6.26 6.26 550.0 1
Lysine-specific demethylase 5A
CHEMBL2424504
 IC50 5.17 5.17 6800.0 2
Lysine-specific demethylase 5A
CHEMBL2424504
 Kd 4.92 4.92 12000.0 1
Prolyl 4-hydroxylase
CHEMBL4523368
 IC50 4.8 4.8 15900.0 1
Lysine-specific demethylase 4E
CHEMBL1293226
 IC50 4.71 4.5367 19600.0 3
PC-3
CHEMBL390
 IC50 4.69 4.69 20330.0 1
Lysine-specific demethylase 2B
CHEMBL3779760
 IC50 4.68 4.68 21000.0 1
Histone lysine demethylase PHF8
CHEMBL1938212
 IC50 4.55 4.55 28000.0 1
MGC-803
CHEMBL3706566
 IC50 4.53 4.53 29310.0 1
Lysine-specific demethylase 4C
CHEMBL6175
 IC50 4.47 4.47 34000.0 1
MCF7
CHEMBL387
 IC50 4.47 4.47 33670.0 1
HepG2
CHEMBL395
 IC50 4.4 4.4 39750.0 1
Lysine-specific demethylase 3A
CHEMBL1938209
 IC50 4.4 4.395 39810.7 2
Lysine-specific demethylase 4A
CHEMBL5896
 IC50 4.35 4.35 44300.0 1
Lysine-specific demethylase 4B
CHEMBL3313832
 IC50 4.14 4.14 73000.0 1
Lysine-specific demethylase 4D
CHEMBL6138
 IC50 4.1 4.1 79000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 3.0 mL.min-1.g-1 Homo sapiens
T1/2 8.25 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Lysine-specific demethylase 6B IC50 = 16.0 nM 7.8 Inhibition of C-terminal FLAG-tagged human KDM6B expressed in expressed in Sf9 c... 30928196
Lysine-specific demethylase 6B IC50 = 28.0 nM 7.55 Inhibition of KDM6B (unknown origin ) by TR-FRET assay 34555614
Lysine-specific demethylase 6B IC50 = 28.0 nM 7.55 Inhibition of KDM6B (1043 to 1643 residues)(unknown origin) by Alphalisa assay 25279926
Lysine-specific demethylase 6A IC50 = 53.0 nM 7.28 Inhibition of KDM6A (919 to 1401 residues)(unknown origin) by Alphalisa assay 25279926
Lysine-specific demethylase 6B IC50 = 60.0 nM 7.22 Inhibition of KDM6B (unknown origin) 32883639
Lysine-specific demethylase 6B IC50 = 60.0 nM 7.22 Inhibition of JMJD3 (unknown origin) by Alphascreen assay 37660833
Histone-lysine N-methyltransferase EZH2 IC50 = 60.0 nM 7.22 Inhibition of EZH2 Y641F mutant (unknown origin) 38214982
Lysine-specific demethylase 6B IC50 = 60.0 nM 7.22 Competitive inhibition of KDM6B (unknown origin) using biotinylated H3K27me3 pep... 25279926
Lysine-specific demethylase 6B IC50 = 60.0 nM 7.22 Inhibition of recombinant human N-terminal His6/Flag-tagged TEV-protease cleavag... 22842901
Lysine-specific demethylase 6B IC50 = 63.1 nM 7.2 Inhibition of KDM6B (unknown origin) 26682034
Lysine-specific demethylase 6B IC50 = 150.0 nM 6.82 Inhibition of JMJD3 (unknown origin) using biotinylated H3K27me3 peptide as subs... 26776360
Lysine-specific demethylase 5B IC50 = 170.0 nM 6.77 Inhibition of KDM5B (unknown origin ) by TR-FRET assay 34555614
Lysine-specific demethylase 5B IC50 = 170.0 nM 6.77 Inhibition of KDM5B (1 to 809 residues)(unknown origin) by Alphalisa assay 25279926
Lysine-specific demethylase 5B IC50 = 170.0 nM 6.77 Inhibition of KDM5B (1 to 809 residues) (unknown origin) AlphaLISA assay 38749268
Lysine-specific demethylase 5C IC50 = 550.0 nM 6.26 Inhibition of KDM5C (2 to 1560 residues)(unknown origin) by Alphalisa assay 25279926
Lysine-specific demethylase 5B IC50 = 1700.0 nM 5.77 Inhibition of KDM5B (unknown origin) 32883639
Lysine-specific demethylase 5B IC50 = 1700.0 nM 5.77 Inhibition of KDM5B (unknown origin) 36931124
Lysine-specific demethylase 6B IC50 = 5000.0 nM 5.3 Inhibition of recombinant human N-terminal His6/Flag-tagged TEV-protease cleavag... 22842901
Lysine-specific demethylase 5A IC50 = 6800.0 nM 5.17 Inhibition of KDM5A (unknown origin ) by TR-FRET assay 34555614
Lysine-specific demethylase 5A IC50 = 6800.0 nM 5.17 Inhibition of KDM5A (1 to 1090 residues)(unknown origin) by Alphalisa assay 25279926

Literature References

PubMed DOI Target Context # Activities
22842901 10.1038/nature11262 Lysine-specific demethylase 6B 7
33691794 10.1186/s13148-021-01037-1 A549 4
22842901 10.1038/nature11262 Unchecked 4
25279926 10.1038/nature13688 Lysine-specific demethylase 6B 3
26682034 10.1039/c4md00291a No relevant target 3
30392349 10.1021/acs.jmedchem.8b01219 Lysine-specific demethylase 5A 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
34843649 10.1021/acs.jmedchem.1c00605 Unchecked 2
38294854 10.1021/acs.jmedchem.3c01820 Methylcytosine dioxygenase TET1 2
38294854 10.1021/acs.jmedchem.3c01820 Methylcytosine dioxygenase TET2 2
30392349 10.1021/acs.jmedchem.8b01219 Unchecked 2
25279926 10.1038/nature13688 Lysine-specific demethylase 4C 2
22842901 10.1038/nature11262 5-hydroxytryptamine receptor 1B 2
38294854 10.1021/acs.jmedchem.3c01820 Methylcytosine dioxygenase TET3 2
22842901 10.1038/nature11262 Lysine-specific demethylase 4A 2
22842901 10.1038/nature11262 5-hydroxytryptamine receptor 2A 2
38294854 10.1021/acs.jmedchem.3c01820 Unchecked 2
26776360 10.1016/j.bmcl.2016.01.006 Liver microsome 2
22842901 10.1038/nature11262 5-hydroxytryptamine receptor 2C 2

Data from ChEMBL 36 via Core Engine