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Compound Detail

CHEMBL3134377

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Cc1ccc(-c2ncc(OC[C@@H]3CCNC3)cc2-c2ccc(C#N)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3134377
Phase Preclinical
Structure Type MOL
InChI Key IQVDLEXWAPYWDT-LJQANCHMSA-N
8
Targets
19
Activities
4
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

369.5
MW (Da)
4.58
ALogP
4
HBA
1
HBD
57.9
PSA (Ų)
0.71
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 C24H23N3O
MW 369.47
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.85

Activity Summary

IC50 15 meas. best 8.0
Kd 2 meas. best 8.1
EC50 1 meas. best 7.21
Ki 1 meas. best 7.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Lysine-specific histone demethylase 1A
CHEMBL6136
 Kd 8.1 8.1 8.0 1
Lysine-specific histone demethylase 1A
CHEMBL6136
 IC50 8.0 7.13 10.0 5
LSD1/CoREST complex
CHEMBL3137262
 Kd 7.85 7.85 14.0 1
LSD1/CoREST complex
CHEMBL3137262
 Ki 7.46 7.46 35.0 1
Lysine-specific histone demethylase 1A
CHEMBL6136
 EC50 7.21 7.21 62.0 1
MV4-11
CHEMBL613835
 IC50 6.91 6.91 122.0 1
NCI-H1417
CHEMBL2366149
 IC50 6.67 6.67 213.0 1
MOLM-13
CHEMBL3706572
 IC50 6.21 6.21 613.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.5 5.5 3200.0 1
SJRH30
CHEMBL1075575
 IC50 5.0 4.9867 9930.0 3
RD
CHEMBL614144
 IC50 4.99 4.9467 10200.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Lysine-specific histone demethylase 1A Kd = 8.0 nM 8.1 Binding affinity to LSD1 (unknown origin) by SPR analysis 28927796
Lysine-specific histone demethylase 1A IC50 = 10.0 nM 8.0 Inhibition of LSD1 (unknown origin) 30409536
LSD1/CoREST complex Kd = 14.0 nM 7.85 Binding affinity to human LSD1/CoREST assessed as dissociation constant by compe... 35525212
Lysine-specific histone demethylase 1A IC50 = 30.0 nM 7.52 Inhibition of LSD1 (unknown origin) using histone H3 (1 to 21) K4(Me1)-biotin pe... -
LSD1/CoREST complex Ki = 35.0 nM 7.46 Inhibition of human LSD1/CoREST using histone H3 peptide as substrate by fluores... 35525212
Lysine-specific histone demethylase 1A IC50 = 41.0 nM 7.39 Inhibition of recombinant human N-terminal truncated LSD1 (151 to 852 residues) ... 28927796
Lysine-specific histone demethylase 1A EC50 = 62.0 nM 7.21 Inhibition of LSD1 in human THP1 cells assessed as induction of CD11b expression... 30409536
MV4-11 IC50 = 122.0 nM 6.91 Antiproliferative activity against human MV4-11 cells assessed as cell growth in... 37849536
Lysine-specific histone demethylase 1A IC50 = 130.0 nM 6.89 Inhibition of human recombinant LSD1 expressed in Escherichia coli using H3K4me2... 37849536
NCI-H1417 IC50 = 213.0 nM 6.67 Antiproliferative activity against human NCI-H1417 cells assessed as cell growth... 37849536
MOLM-13 IC50 = 613.0 nM 6.21 Antiproliferative activity against human MOLM-13 cells assessed as cell growth i... 37849536
Lysine-specific histone demethylase 1A IC50 = 1400.0 nM 5.85 Inhibition of LSD1 in human THP1 cells assessed as CD86 level after 24 hrs by EL... -
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3200.0 nM 5.5 Inhibition of human ERG expressed in CHO cells by Ionworks electrophysiology met... 28927796
SJRH30 IC50 = 9930.0 nM 5.0 Antiproliferative activity against human Rh30 cells assessed as inhibition of ce... 35525212
RD IC50 = 10200.0 nM 4.99 Antiproliferative activity against human RD cells assessed as inhibition of cell... 35525212
SJRH30 IC50 = 10300.0 nM 4.99 Antiproliferative activity against human Rh30 cells assessed as inhibition of ce... 35525212
SJRH30 IC50 = 10700.0 nM 4.97 Antiproliferative activity against human Rh30 cells assessed as inhibition of ce... 35525212
RD IC50 = 11430.0 nM 4.94 Antiproliferative activity against human RD cells assessed as inhibition of cell... 35525212
RD IC50 = 12350.0 nM 4.91 Antiproliferative activity against human RD cells assessed as inhibition of cell... 35525212

Literature References

PubMed DOI Target Context # Activities
35525212 10.1016/j.ejmech.2022.114410 SJRH30 5
35525212 10.1016/j.ejmech.2022.114410 RD 4
- 10.1039/C3MD00226H Lysine-specific histone demethylase 1A 3
28927796 10.1016/j.bmcl.2017.08.052 Lysine-specific histone demethylase 1A 3
30409536 10.1016/j.bmcl.2018.11.001 Lysine-specific histone demethylase 1A 2
35525212 10.1016/j.ejmech.2022.114410 LSD1/CoREST complex 2
35525212 10.1016/j.ejmech.2022.114410 Lysine-specific histone demethylase 1A 2
- 10.1039/C3MD00226H THP-1 1
- 10.1039/C3MD00226H Amine oxidase [flavin-containing] A 1
28927796 10.1016/j.bmcl.2017.08.052 Voltage-gated inwardly rectifying potassium channel KCNH2 1
30409536 10.1016/j.bmcl.2018.11.001 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37849536 10.1021/acsmedchemlett.3c00292 Lysine-specific histone demethylase 1A 1
37849536 10.1021/acsmedchemlett.3c00292 MOLM-13 1
37849536 10.1021/acsmedchemlett.3c00292 MV4-11 1
37849536 10.1021/acsmedchemlett.3c00292 NCI-H1417 1

Data from ChEMBL 36 via Core Engine