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Compound Detail

CHEMBL5633837

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COc1cc(-c2n[nH]c3ncc(-c4ccc(C)c(NCCO)c4)cc23)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5633837
Phase Preclinical
Structure Type MOL
InChI Key OATHVDKMFZZHHN-UHFFFAOYSA-N
22
Targets
28
Activities
2
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

434.5
MW (Da)
4.03
ALogP
7
HBA
3
HBD
101.5
PSA (Ų)
0.38
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H26N4O4
MW 434.50
Aromatic Rings 4
Heavy Atoms 32
NP-Likeness -0.81

Activity Summary

IC50 17 meas. best 10.27
Kd 11 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 10.27 10.27 0.1 1
MV4-11
CHEMBL613835
 IC50 9.84 9.84 0.1 2
A549
CHEMBL392
 IC50 9.77 9.77 0.2 1
Bone morphogenetic protein receptor type-1B
CHEMBL5476
 Kd 9.52 9.52 0.3 1
Mitogen-activated protein kinase 10
CHEMBL2637
 Kd 8.59 8.59 2.6 1
Dual specificity mitogen-activated protein kinase kinase 5
CHEMBL4948
 Kd 8.17 8.17 6.7 1
MOLT-4
CHEMBL614177
 IC50 8.17 8.17 6.8 1
HT-29
CHEMBL384
 IC50 8.1 8.1 8.0 1
Serine/threonine-protein kinase 16
CHEMBL3938
 Kd 7.96 7.96 11.0 1
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 7.94 7.94 11.6 1
Tyrosine-protein kinase ABL1
CHEMBL1862
 Kd 7.85 7.85 14.0 1
Mitogen-activated protein kinase 9
CHEMBL4179
 Kd 7.85 7.85 14.0 1
PLC-PRF-5
CHEMBL1075561
 IC50 7.67 7.67 21.6 1
MDA-MB-231
CHEMBL400
 IC50 7.6 7.6 25.1 1
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 Kd 7.58 7.51 26.0 3
Myotonin-protein kinase
CHEMBL5320
 Kd 7.52 7.52 30.0 1
Mitogen-activated protein kinase 8
CHEMBL2276
 Kd 7.44 7.44 36.0 1
THP-1
CHEMBL614245
 IC50 7.11 7.11 78.0 1
Tyrosine-protein kinase ABL1
CHEMBL1862
 IC50 7.05 7.05 88.1 1
MCF7
CHEMBL387
 IC50 6.91 6.91 123.8 1
A549/TR
CHEMBL4483226
 IC50 6.78 6.78 168.0 1
PANC-1
CHEMBL614139
 IC50 6.65 6.65 224.9 1
K562/Adr
CHEMBL4296449
 IC50 6.16 6.16 693.0 1
Unchecked
CHEMBL612545
 IC50 5.71 5.71 1940.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1147.8 ng.hr.mL-1 Mus musculus
AUC 110.0 ng.hr.mL-1 Mus musculus
CL 73.33 mL.min-1.kg-1 Mus musculus
Cmax 3.845 ug.mL-1 Mus musculus
Cmax 0.115 ug.mL-1 Mus musculus
F 3.2 % Mus musculus
T1/2 1.3 hr Mus musculus
T1/2 1.2 hr Mus musculus
Tmax 0.1 hr Mus musculus
Tmax 0.3 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 IC50 = 0.054 nM 10.27 Antiproliferative activity against human HCT-116 cells assessed as inhibition of... 37544183
MV4-11 IC50 = 0.144 nM 9.84 Antiproliferative activity against human MV4-11 cells assessed as inhibition of ... 37544183
MV4-11 IC50 = 0.144 nM 9.84 Antiproliferative activity against human MV4-11 cells transfected with FLT3-ITD ... 37544183
A549 IC50 = 0.169 nM 9.77 Antiproliferative activity against human A549 cells assessed as inhibition of ce... 37544183
Bone morphogenetic protein receptor type-1B Kd = 0.3 nM 9.52 Binding affinity to human BMPR1B assessed as dissociation constant by Adp-glo as... 37544183
Mitogen-activated protein kinase 10 Kd = 2.6 nM 8.59 Binding affinity to human JNK3 assessed as dissociation constant by Adp-glo assa... 37544183
MOLT-4 IC50 = 6.794 nM 8.17 Antiproliferative activity against human MOLT-4 cells assessed as inhibition of ... 37544183
Dual specificity mitogen-activated protein kinase kinase 5 Kd = 6.7 nM 8.17 Binding affinity to human MEK5 assessed as dissociation constant by Adp-glo assa... 37544183
HT-29 IC50 = 7.985 nM 8.1 Antiproliferative activity against human HT-29 cells assessed as inhibition of c... 37544183
Serine/threonine-protein kinase 16 Kd = 11.0 nM 7.96 Binding affinity to human STK16 assessed as dissociation constant by Adp-glo ass... 37544183
Receptor-type tyrosine-protein kinase FLT3 IC50 = 11.6 nM 7.94 Inhibition of human FLT3 using MBP as substrate in presence of ATP by microplate... 37544183
Mitogen-activated protein kinase 9 Kd = 14.0 nM 7.85 Binding affinity to human JNK2 assessed as dissociation constant by Adp-glo assa... 37544183
Tyrosine-protein kinase ABL1 Kd = 14.0 nM 7.85 Binding affinity to human ABL1 assessed as dissociation constant by Adp-glo assa... 37544183
PLC-PRF-5 IC50 = 21.55 nM 7.67 Antiproliferative activity against human PLC-PRF-5 cells assessed as inhibition ... 37544183
MDA-MB-231 IC50 = 25.14 nM 7.6 Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition... 37544183
Receptor-type tyrosine-protein kinase FLT3 Kd = 26.0 nM 7.58 Binding affinity to human FLT3 assessed as dissociation constant by Adp-glo assa... 37544183
Myotonin-protein kinase Kd = 30.0 nM 7.52 Binding affinity to human DMPK assessed as dissociation constant by Adp-glo assa... 37544183
Receptor-type tyrosine-protein kinase FLT3 Kd = 33.0 nM 7.48 Binding affinity to human FLT3 ITD/D835V double mutant assessed as dissociation ... 37544183
Receptor-type tyrosine-protein kinase FLT3 Kd = 34.0 nM 7.47 Binding affinity to human FLT3 ITD mutant assessed as dissociation constant by A... 37544183
Mitogen-activated protein kinase 8 Kd = 36.0 nM 7.44 Binding affinity to human JNK1 assessed as dissociation constant by Adp-glo assa... 37544183

Literature References

PubMed DOI Target Context # Activities
37544183 10.1016/j.ejmech.2023.115687 ADMET 12
37544183 10.1016/j.ejmech.2023.115687 Receptor-type tyrosine-protein kinase FLT3 8
37544183 10.1016/j.ejmech.2023.115687 MV4-11 6
37544183 10.1016/j.ejmech.2023.115687 HCT-116 5
37544183 10.1016/j.ejmech.2023.115687 Unchecked 5
37544183 10.1016/j.ejmech.2023.115687 K562 3
37544183 10.1016/j.ejmech.2023.115687 Tyrosine-protein kinase ABL1 3
37544183 10.1016/j.ejmech.2023.115687 Mitogen-activated protein kinase 10 2
37544183 10.1016/j.ejmech.2023.115687 Mitogen-activated protein kinase 9 2
37544183 10.1016/j.ejmech.2023.115687 Mitogen-activated protein kinase 8 2
37544183 10.1016/j.ejmech.2023.115687 Myotonin-protein kinase 2
37544183 10.1016/j.ejmech.2023.115687 Bone morphogenetic protein receptor type-1B 2
37544183 10.1016/j.ejmech.2023.115687 Dual specificity mitogen-activated protein kinase kinase 5 2
37544183 10.1016/j.ejmech.2023.115687 Serine/threonine-protein kinase 16 2
37544183 10.1016/j.ejmech.2023.115687 A549/TR 1
37544183 10.1016/j.ejmech.2023.115687 PANC-1 1
37544183 10.1016/j.ejmech.2023.115687 PLC-PRF-5 1
37544183 10.1016/j.ejmech.2023.115687 MCF7 1
37544183 10.1016/j.ejmech.2023.115687 A549 1
37544183 10.1016/j.ejmech.2023.115687 HT-29 1

Data from ChEMBL 36 via Core Engine