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Compound Detail

CHEMBL4744689

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Nc1ncc(-c2nc(N3CCOCC3)c3ccn(CCCCCCC(=O)NO)c3n2)cn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4744689
Phase Preclinical
Structure Type MOL
InChI Key YLDAIYDYJXZDGW-UHFFFAOYSA-N
31
Targets
38
Activities
3
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

440.5
MW (Da)
1.76
ALogP
10
HBA
3
HBD
144.3
PSA (Ų)
0.26
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H28N8O3
MW 440.51
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.25

Activity Summary

IC50 31 meas. best 9.18
Kd 5 meas. best 7.92
EC50 2 meas. best 6.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 9.18 9.18 0.7 1
Histone deacetylase 1
CHEMBL325
 IC50 8.82 8.82 1.5 2
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 8.64 8.64 2.3 1
Histone deacetylase 2
CHEMBL1937
 IC50 8.39 8.39 4.1 1
Histone deacetylase 6
CHEMBL1865
 IC50 8.18 8.18 6.6 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
CHEMBL4005
 IC50 7.96 7.96 11.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
CHEMBL4005
 Kd 7.92 7.92 12.0 1
PI3-kinase p110-alpha/p85-alpha
CHEMBL2111367
 IC50 7.6 7.6 25.0 1
MV4-11
CHEMBL613835
 IC50 7.36 7.36 44.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
CHEMBL3130
 IC50 7.2 7.2 63.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform
CHEMBL3145
 IC50 7.06 7.06 87.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
CHEMBL3267
 IC50 7.04 7.04 92.0 1
Serine/threonine-protein kinase mTOR
CHEMBL2842
 IC50 7.0 7.0 101.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
CHEMBL3267
 Kd 7.0 7.0 100.0 1
Unchecked
CHEMBL612545
 EC50 6.89 6.89 130.0 1
MOLT-4
CHEMBL614177
 IC50 6.82 6.82 150.0 1
Histone deacetylase 6
CHEMBL1865
 EC50 6.66 6.66 220.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
CHEMBL3130
 Kd 6.62 6.62 240.0 2
SU-DHL-6
CHEMBL4296496
 IC50 6.6 6.6 250.0 1
Phosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit beta
CHEMBL5554
 Kd 6.58 6.58 260.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.57 6.57 270.0 1
Raji
CHEMBL614628
 IC50 6.55 6.55 280.0 1
K562
CHEMBL385
 IC50 6.36 6.36 440.0 1
Ramos
CHEMBL614629
 IC50 6.31 6.31 490.0 1
DNA-dependent protein kinase catalytic subunit
CHEMBL3142
 IC50 6.23 6.23 594.0 1
Huh-7
CHEMBL614039
 IC50 6.19 6.19 650.0 1
HepG2
CHEMBL395
 IC50 5.98 5.98 1050.0 1
Phosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit beta
CHEMBL5554
 IC50 5.98 5.98 1046.0 1
SK-HEP1
CHEMBL614912
 IC50 5.84 5.84 1460.0 1
PC-3
CHEMBL390
 IC50 5.8 5.8 1570.0 1
SNU-398
CHEMBL614454
 IC50 5.78 5.78 1660.0 1
Hep 3B2
CHEMBL4296437
 IC50 5.54 5.54 2870.0 1
PLC-PRF-5
CHEMBL1075561
 IC50 5.52 5.52 3050.0 1
SNU-387
CHEMBL1075583
 IC50 5.41 5.41 3900.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 5.2 5.2 6300.0 1
Phosphatidylinositol 3-kinase catalytic subunit type 3
CHEMBL1075165
 IC50 5.2 5.2 6295.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.0 hr Homo sapiens
T1/2 0.65 hr Mus musculus
t1/2 - - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 0.66 nM 9.18 Inhibition of recombinant human C-terminal His-tagged HDAC3 (1 to 428 end residu... 29360358
Histone deacetylase 1 IC50 = 1.5 nM 8.82 Inhibition of HDAC1 in human HeLa nuclear extract using Boc-Lys(Ac)-AMC as subst... 29360358
Histone deacetylase 1 IC50 = 1.5 nM 8.82 Inhibition of full length recombinant human C-terminal FLAG/His-tagged HDAC1 (1 ... 29360358
Polyamine deacetylase HDAC10 IC50 = 2.3 nM 8.64 Inhibition of N-terminal FLAG-tagged human HDAC10 (2 to 631 residues) expressed ... 29360358
Histone deacetylase 2 IC50 = 4.1 nM 8.39 Inhibition of HDAC2 (unknown origin) using fluorogenic HDAC substrate 3 incubate... 29360358
Histone deacetylase 6 IC50 = 6.6 nM 8.18 Inhibition of recombinant human N-terminal GST-tagged HDAC6 expressed in baculov... 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 11.0 nM 7.96 Inhibition of human PI3Kalpha incubated for 1 hr by ADP-Glo kinase assay 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Kd = 12.0 nM 7.92 Inhibition of human wild type partial length PI3Kalpha (R108 to N1068 residues) ... 29360358
PI3-kinase p110-alpha/p85-alpha IC50 = 25.0 nM 7.6 Inhibition of human full-length recombinant p110alpha/p85alpha co-expressed in b... 29360358
MV4-11 IC50 = 44.0 nM 7.36 Antiproliferative activity against human MV4-11 cells assessed as reduction in c... 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 63.0 nM 7.2 Inhibition of human PI3Kdelta incubated for 1 hr by ADP-Glo kinase assay 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform IC50 = 87.0 nM 7.06 Inhibition of human PI3Kbeta incubated for 1 hr by ADP-Glo kinase assay 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform IC50 = 92.0 nM 7.04 Inhibition of human PI3Kgamma incubated for 1 hr by ADP-Glo kinase assay 29360358
Serine/threonine-protein kinase mTOR IC50 = 101.0 nM 7.0 Inhibition of human mTOR 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform Kd = 100.0 nM 7.0 Inhibition of human wild type partial length PI3Kgamma (S144 to A1102 residues) ... 29360358
Unchecked EC50 = 130.0 nM 6.89 Inhibition of PI3K/AKT/mTOR signaling in human HepG2 cells assessed as reduction... 29360358
MOLT-4 IC50 = 150.0 nM 6.82 Antiproliferative activity against human MOLT-4 cells assessed as reduction in c... 29360358
Histone deacetylase 6 EC50 = 220.0 nM 6.66 Inhibition of HDAC6 in human MCF7 cells assessed as increase in acetylated alpha... 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform Kd = 240.0 nM 6.62 Inhibition of human wild type partial length PI3Kdelta (R108 to Q1044 residues) ... 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform Kd = 240.0 nM 6.62 Inhibition of human PI3Kdelta incubated for 1 hr by ADP-Glo kinase assay 29360358

Literature References

PubMed DOI Target Context # Activities
29360358 10.1021/acs.jmedchem.7b01465 Unchecked 20
29360358 10.1021/acs.jmedchem.7b01465 ADMET 6
29360358 10.1021/acs.jmedchem.7b01465 Histone deacetylase 6 6
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform 3
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform 2
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 2
29360358 10.1021/acs.jmedchem.7b01465 Histone deacetylase 1 2
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit beta 2
29360358 10.1021/acs.jmedchem.7b01465 Histone deacetylase 2
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit alpha 2
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 3-kinase catalytic subunit type 3 2
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform 2
29360358 10.1021/acs.jmedchem.7b01465 Serine/threonine-protein kinase mTOR 2
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4-kinase beta 2
29360358 10.1021/acs.jmedchem.7b01465 DNA-dependent protein kinase catalytic subunit 2
29360358 10.1021/acs.jmedchem.7b01465 Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) 1
29360358 10.1021/acs.jmedchem.7b01465 Histone deacetylase 5 1
29360358 10.1021/acs.jmedchem.7b01465 Histone deacetylase 4 1
29360358 10.1021/acs.jmedchem.7b01465 Voltage-gated inwardly rectifying potassium channel KCNH2 1
29360358 10.1021/acs.jmedchem.7b01465 Huh-7 1

Data from ChEMBL 36 via Core Engine