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Compound Detail

CHEMBL4749655

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O=C(CCCCCCn1cnc2c(N3CCOCC3)nc(-c3cccc(CO)c3)nc21)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4749655
Phase Preclinical
Structure Type MOL
InChI Key JBFFDSGEOZGWCK-UHFFFAOYSA-N
36
Targets
56
Activities
3
Assay Types
20
PK Parameters
20
Publications
0
Known Names

Molecular Properties

454.5
MW (Da)
2.28
ALogP
9
HBA
3
HBD
125.6
PSA (Ų)
0.24
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H30N6O4
MW 454.53
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -1.10

Activity Summary

IC50 47 meas. best 8.96
Kd 5 meas. best 8.46
EC50 4 meas. best 7.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 8.96 8.96 1.1 1
Histone deacetylase 1
CHEMBL325
 IC50 8.96 8.8625 1.1 4
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 8.6 8.6 2.5 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
CHEMBL4005
 Kd 8.46 8.46 3.5 1
Histone deacetylase 6
CHEMBL1865
 IC50 8.38 8.38 4.2 2
Phosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit beta
CHEMBL5554
 Kd 8.31 8.31 4.9 1
Histone deacetylase 2
CHEMBL1937
 IC50 8.22 8.22 6.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
CHEMBL4005
 IC50 7.55 7.55 28.0 3
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
CHEMBL3130
 IC50 7.43 7.43 37.0 2
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
CHEMBL3130
 Kd 7.39 7.39 41.0 2
MV4-11
CHEMBL613835
 IC50 7.33 7.33 47.0 1
PI3-kinase p110-alpha/p85-alpha
CHEMBL2111367
 IC50 7.3 7.3 50.0 1
MV4-11
CHEMBL613835
 EC50 7.19 6.795 64.0 2
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
CHEMBL3267
 Kd 7.07 7.07 86.0 1
Phosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit beta
CHEMBL5554
 IC50 6.99 6.99 103.0 1
MOLT-4
CHEMBL614177
 IC50 6.85 6.85 140.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
CHEMBL3267
 IC50 6.75 6.75 177.0 1
Histone deacetylase 6
CHEMBL1865
 EC50 6.72 6.72 190.0 1
SU-DHL-6
CHEMBL4296496
 IC50 6.72 6.72 190.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform
CHEMBL3145
 IC50 6.67 6.67 212.0 1
Raji
CHEMBL614628
 IC50 6.62 6.62 240.0 1
NCI-H460
CHEMBL396
 IC50 6.51 6.28 310.0 2
Histone deacetylase 8
CHEMBL3192
 IC50 6.5 6.5 320.0 1
K562
CHEMBL385
 IC50 6.46 6.46 350.0 1
Huh-7
CHEMBL614039
 IC50 6.41 6.365 390.0 2
Ramos
CHEMBL614629
 IC50 6.4 6.4 400.0 1
Unchecked
CHEMBL612545
 EC50 6.24 6.24 580.0 1
HepG2
CHEMBL395
 IC50 6.23 6.23 590.0 1
Hep 3B2
CHEMBL4296437
 IC50 6.21 6.055 610.0 2
SK-HEP1
CHEMBL614912
 IC50 6.1 6.1 790.0 1
Unchecked
CHEMBL612545
 IC50 6.04 5.965 910.0 2
PC-3
CHEMBL390
 IC50 5.97 5.97 1080.0 1
PLC-PRF-5
CHEMBL1075561
 IC50 5.91 5.91 1240.0 1
Histone deacetylase 9
CHEMBL4145
 IC50 5.89 5.89 1282.0 1
SNU-398
CHEMBL614454
 IC50 5.86 5.86 1380.0 1
Serine/threonine-protein kinase mTOR
CHEMBL2842
 IC50 5.71 5.71 1946.0 1
Histone deacetylase 7
CHEMBL2716
 IC50 5.64 5.64 2305.0 1
SNU-387
CHEMBL1075583
 IC50 5.58 5.58 2640.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 5.34 5.34 4591.0 1
Histone deacetylase 5
CHEMBL2563
 IC50 5.32 5.32 4800.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 5.01 5.01 9700.0 1
DNA-dependent protein kinase catalytic subunit
CHEMBL3142
 IC50 5.0 5.0 10000.0 1
Phosphatidylinositol 3-kinase catalytic subunit type 3
CHEMBL1075165
 IC50 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 7581.56 ng.hr.mL-1 Mus musculus
AUC 440.89 ng.hr.mL-1 Mus musculus
AUC 4118.04 ng.hr.mL-1 Mus musculus
CL 0.19 uL/min/pmol Homo sapiens
CL 110.0 mL.min-1.kg-1 Mus musculus
Cmax 3900.0 nM Mus musculus
Cmax 10100.0 nM Mus musculus
F 5.8 % Mus musculus
F 18.1 % Mus musculus
T1/2 6.0 hr Mus musculus
T1/2 1.0 hr Homo sapiens
T1/2 1.0 hr Mus musculus
T1/2 0.9167 hr Rattus norvegicus
T1/2 4.59 hr Mus musculus
T1/2 2.01 hr Mus musculus
T1/2 4.41 hr Mus musculus
T1/2 6.5 hr Mus musculus
T1/2 11.1 hr Mus musculus
Tmax 0.17 hr Mus musculus
Tmax 0.5 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 1 IC50 = 1.1 nM 8.96 Inhibition of full length recombinant human C-terminal FLAG/His-tagged HDAC1 (1 ... 29360358
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 1.1 nM 8.96 Inhibition of recombinant human C-terminal His-tagged HDAC3 (1 to 428 end residu... 29360358
Histone deacetylase 1 IC50 = 1.1 nM 8.96 Inhibition of full-length HDAC1 (unknown origin) by Color-de-Lys assay 34894440
Histone deacetylase 1 IC50 = 1.1 nM 8.96 Inhibition of human recombinant HDAC1 using Boc-Lys(Ac)-AMC as substrate preincu... 38183777
Polyamine deacetylase HDAC10 IC50 = 2.5 nM 8.6 Inhibition of N-terminal FLAG-tagged human HDAC10 (2 to 631 residues) expressed ... 29360358
Histone deacetylase 1 IC50 = 2.7 nM 8.57 Inhibition of HDAC1 in human HeLa nuclear extract using Boc-Lys(Ac)-AMC as subst... 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Kd = 3.5 nM 8.46 Inhibition of human wild type partial length PI3Kalpha (R108 to N1068 residues) ... 29360358
Histone deacetylase 6 IC50 = 4.2 nM 8.38 Inhibition of recombinant human N-terminal GST-tagged HDAC6 expressed in baculov... 29360358
Histone deacetylase 6 IC50 = 4.2 nM 8.38 Inhibition of human HDAC6 using fluorogenic-(RHKKAc) as substrate by fluorescenc... 38183777
Phosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit beta Kd = 4.9 nM 8.31 Inhibition of PI3K2beta (unknown origin) 29360358
Histone deacetylase 2 IC50 = 6.0 nM 8.22 Inhibition of HDAC2 (unknown origin) using fluorogenic HDAC substrate 3 incubate... 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 28.0 nM 7.55 Inhibition of PI3Kalpha (unknown origin) using PIP2 as substrate preincubated fo... 38183777
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 28.0 nM 7.55 Inhibition of human PI3Kalpha incubated for 1 hr by ADP-Glo kinase assay 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 28.0 nM 7.55 Inhibition of PI3Kalpha (unknown origin) expressed in baculovirus expression sys... 34894440
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 37.0 nM 7.43 Inhibition of PI3Kdelta (unknown origin) using PIP2 as substrate preincubated fo... 38183777
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform IC50 = 37.0 nM 7.43 Inhibition of human PI3Kdelta incubated for 1 hr by ADP-Glo kinase assay 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform Kd = 41.0 nM 7.39 Inhibition of human PI3Kdelta incubated for 1 hr by ADP-Glo kinase assay 29360358
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform Kd = 41.0 nM 7.39 Inhibition of human wild type partial length PI3Kdelta (R108 to Q1044 residues) ... 29360358
MV4-11 IC50 = 47.0 nM 7.33 Antiproliferative activity against human MV4-11 cells assessed as reduction in c... 29360358
PI3-kinase p110-alpha/p85-alpha IC50 = 50.0 nM 7.3 Inhibition of human full-length recombinant p110alpha/p85alpha co-expressed in b... 29360358

Literature References

PubMed DOI Target Context # Activities
29360358 10.1021/acs.jmedchem.7b01465 ADMET 37
29360358 10.1021/acs.jmedchem.7b01465 Unchecked 36
29360358 10.1021/acs.jmedchem.7b01465 Histone deacetylase 6 11
29360358 10.1021/acs.jmedchem.7b01465 HepG2 7
29360358 10.1021/acs.jmedchem.7b01465 Histone deacetylase 5
29360358 10.1021/acs.jmedchem.7b01465 Hep 3B2 4
29360358 10.1021/acs.jmedchem.7b01465 Huh-7 3
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform 3
29360358 10.1021/acs.jmedchem.7b01465 MV4-11 3
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 2
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 gamma isoform 2
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 3-kinase catalytic subunit type 3 2
29360358 10.1021/acs.jmedchem.7b01465 Serine/threonine-protein kinase mTOR 2
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit beta 2
29360358 10.1021/acs.jmedchem.7b01465 DNA-dependent protein kinase catalytic subunit 2
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4-kinase beta 2
29360358 10.1021/acs.jmedchem.7b01465 Phosphatidylinositol 4-phosphate 3-kinase C2 domain-containing subunit alpha 2
29360358 10.1021/acs.jmedchem.7b01465 Histone deacetylase 1 2
29360358 10.1021/acs.jmedchem.7b01465 NCI-H460 2

Data from ChEMBL 36 via Core Engine