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Compound Detail

CHEMBL3774537

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O=c1[nH]cnc2c(-n3cc(CCN4CCC(c5cccc(Cl)c5)CC4)cn3)nccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3774537
Phase Preclinical
Structure Type MOL
InChI Key LDSDVQOOEYCWQS-UHFFFAOYSA-N
6
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

434.9
MW (Da)
3.58
ALogP
6
HBA
1
HBD
79.7
PSA (Ų)
0.52
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H23ClN6O
MW 434.93
Aromatic Rings 4
Heavy Atoms 31
NP-Likeness -1.44

Activity Summary

IC50 8 meas. best 7.64
EC50 4 meas. best 6.22
Ki 2 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Lysine-specific demethylase 5B
CHEMBL3774295
 Ki 8.7 8.7 2.0 1
Lysine-specific demethylase 4A
CHEMBL5896
 Ki 8.52 8.52 3.0 1
Lysine-specific demethylase 5B
CHEMBL3774295
 IC50 7.64 7.64 23.0 2
Lysine-specific demethylase 4B
CHEMBL3313832
 IC50 7.51 7.51 31.0 2
Lysine-specific demethylase 5C
CHEMBL2163176
 IC50 7.19 7.19 65.0 1
Lysine-specific demethylase 4A
CHEMBL5896
 IC50 6.99 6.99 102.0 1
Lysine-specific demethylase 5B
CHEMBL3774295
 EC50 6.22 5.42 600.0 2
Lysine-specific demethylase 4B
CHEMBL3313832
 EC50 6.0 6.0 1000.0 1
Lysine-specific demethylase 3A
CHEMBL1938209
 IC50 5.28 5.28 5300.0 1
Lysine-specific demethylase 4A
CHEMBL5896
 EC50 5.07 5.07 8500.0 1
Lysine-specific demethylase 2A
CHEMBL1938210
 IC50 4.89 4.89 12900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Lysine-specific demethylase 5B Ki = 2.0 nM 8.7 Binding affinity to KDM5B (unknown origin) 31158747
Lysine-specific demethylase 4A Ki = 3.0 nM 8.52 Binding affinity to KDM4A (unknown origin) 31158747
Lysine-specific demethylase 5B IC50 = 23.0 nM 7.64 Inhibition of KDM5B (unknown origin) using biotin-H3K4me3 as substrate preincuba... 26741168
Lysine-specific demethylase 5B IC50 = 23.0 nM 7.64 Inhibition of human KDM5B using H3(1-21)K4-Me3-GGK Biotin as substrate and measu... 35838529
Lysine-specific demethylase 4B IC50 = 31.0 nM 7.51 Inhibition of recombinant human N-terminal GST-tagged KDM4B (1 to 500 residues) ... 26741168
Lysine-specific demethylase 4B IC50 = 31.0 nM 7.51 Inhibition of N-terminal GST-tagged recombinant human KDM4B (1 to 500 residues) ... 35838529
Lysine-specific demethylase 5C IC50 = 65.0 nM 7.19 Inhibition of KDM5C (unknown origin) using biotin-H3K4me3 as substrate preincuba... 26741168
Lysine-specific demethylase 4A IC50 = 102.0 nM 6.99 Inhibition of human N-terminal His-tagged KDM4A (1 to 359 residues) expressed in... 26741168
Lysine-specific demethylase 5B EC50 = 600.0 nM 6.22 Binding affinity to recombinant human N-terminal KDM5B (26 to 772 residues) fuse... 31158747
Lysine-specific demethylase 4B EC50 = 1000.0 nM 6.0 Binding affinity to recombinant human N-terminal KDM4B (1 to 348 residues) fused... 31158747
Lysine-specific demethylase 3A IC50 = 5300.0 nM 5.28 Inhibition of KDM3A (unknown origin) using biotin-H3K9me2 (1 to 21 residues) as ... 26741168
Lysine-specific demethylase 4A EC50 = 8500.0 nM 5.07 Inhibition of FLAG tagged full length wild type human KDM4A transfected in HeLa ... 31158747
Lysine-specific demethylase 2A IC50 = 12900.0 nM 4.89 Inhibition of KDM2A (unknown origin) using biotin-H3K36me2 (28 to 48 residues) a... 26741168
Lysine-specific demethylase 5B EC50 = 24200.0 nM 4.62 Inhibition of full length human wild type KDM5B transfected in HeLa cells assess... 31158747

Literature References

PubMed DOI Target Context # Activities
26741168 10.1021/acs.jmedchem.5b01635 ADMET 4
26741168 10.1021/acs.jmedchem.5b01635 Lysine-specific demethylase 4A 3
31158747 10.1016/j.ejmech.2019.05.041 Lysine-specific demethylase 5B 3
26741168 10.1021/acs.jmedchem.5b01635 Lysine-specific demethylase 5B 3
31158747 10.1016/j.ejmech.2019.05.041 Lysine-specific demethylase 4A 2
26741168 10.1021/acs.jmedchem.5b01635 Lysine-specific demethylase 5C 1
26741168 10.1021/acs.jmedchem.5b01635 Lysine-specific demethylase 2A 1
26741168 10.1021/acs.jmedchem.5b01635 Lysine-specific demethylase 3A 1
26741168 10.1021/acs.jmedchem.5b01635 Lysine-specific demethylase 6B 1
26741168 10.1021/acs.jmedchem.5b01635 AMP-activated protein kinase, AMPK 1
26741168 10.1021/acs.jmedchem.5b01635 Aurora kinase B 1
26741168 10.1021/acs.jmedchem.5b01635 Calcium/calmodulin-dependent protein kinase kinase 2 1
26741168 10.1021/acs.jmedchem.5b01635 Calcium/calmodulin-dependent protein kinase type 1 1
26741168 10.1021/acs.jmedchem.5b01635 Serine/threonine-protein kinase Chk2 1
26741168 10.1021/acs.jmedchem.5b01635 Dual specificity mitogen-activated protein kinase kinase 1 1
26741168 10.1021/acs.jmedchem.5b01635 Mitogen-activated protein kinase 8 1
35838529 10.1021/acs.jmedchem.2c00680 ADMET 1
26741168 10.1021/acs.jmedchem.5b01635 Ribosomal protein S6 kinase alpha-1 1
26741168 10.1021/acs.jmedchem.5b01635 3-phosphoinositide-dependent protein kinase 1 1
26741168 10.1021/acs.jmedchem.5b01635 Lysine-specific demethylase 4B 1

Data from ChEMBL 36 via Core Engine