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Compound Detail

CHEMBL5559304

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COc1cc(Nc2nccc(-c3cc(C(=O)N[C@@H](C)CN4CCC4)n(C)n3)n2)cc(OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5559304
Phase Preclinical
Structure Type MOL
InChI Key YLCFOHVAOBLAIK-HNNXBMFYSA-N
18
Targets
21
Activities
1
Assay Types
29
PK Parameters
20
Publications
0
Known Names

Molecular Properties

451.5
MW (Da)
2.46
ALogP
9
HBA
2
HBD
106.4
PSA (Ų)
0.51
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H29N7O3
MW 451.53
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -1.65

Activity Summary

IC50 21 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase SYK
CHEMBL2599
 IC50 8.52 8.335 3.0 2
Syk protein
CHEMBL1932898
 IC50 7.57 6.34 27.0 2
BaF3
CHEMBL614524
 IC50 7.57 6.34 27.0 2
Interferon-induced, double-stranded RNA-activated protein kinase
CHEMBL5785
 IC50 7.1 7.1 79.0 1
Proto-oncogene tyrosine-protein kinase ROS
CHEMBL5568
 IC50 6.96 6.96 110.0 1
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 6.74 6.74 182.0 1
Tyrosine-protein kinase ZAP-70
CHEMBL2803
 IC50 6.72 6.72 191.0 1
Protein kinase C beta type
CHEMBL3045
 IC50 6.62 6.62 239.0 1
Muscle, skeletal receptor tyrosine-protein kinase
CHEMBL5684
 IC50 6.59 6.59 257.0 1
cAMP-dependent protein kinase catalytic subunit alpha
CHEMBL4101
 IC50 6.35 6.35 450.0 1
Platelet-derived growth factor receptor alpha
CHEMBL2007
 IC50 6.25 6.25 567.0 1
Unchecked
CHEMBL612545
 IC50 6.2 6.2 628.0 1
High affinity nerve growth factor receptor
CHEMBL2815
 IC50 6.16 6.16 697.0 1
SU-DHL-6
CHEMBL4296496
 IC50 6.15 6.15 702.4 1
Mitogen-activated protein kinase kinase kinase 3
CHEMBL5970
 IC50 6.13 6.13 738.0 1
Tyrosine-protein kinase Fer
CHEMBL3982
 IC50 6.1 6.1 802.0 1
Homeodomain-interacting protein kinase 1
CHEMBL5427
 IC50 6.1 6.1 798.0 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 6.01 6.01 980.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 7.59 uM.hr Mus musculus
AUC 7.16 uM.hr Mus musculus
AUC 5.08 uM.hr Rattus norvegicus
AUC 5.93 uM.hr Rattus norvegicus
AUC 2.13 uM.hr Canis lupus familiaris
AUC 10.1 uM.hr Canis lupus familiaris
CL 37.0 mL.min-1.kg-1 Rattus norvegicus
CL 0.0096 mL.min-1.kg-1 Homo sapiens
CL 25.18 mL.min-1.kg-1 Mus musculus
CL 36.3 mL.min-1.kg-1 Rattus norvegicus
CL 18.8 mL.min-1.kg-1 Canis lupus familiaris
Cmax 2330.0 nM Mus musculus
Cmax 860.0 nM Mus musculus
Cmax 890.0 nM Rattus norvegicus
Cmax 396.0 nM Rattus norvegicus
Cmax 240.0 nM Canis lupus familiaris
Cmax 477.0 nM Canis lupus familiaris
F 47.2 % Mus musculus
F 58.4 % Rattus norvegicus
F 95.0 % Canis lupus familiaris
T1/2 2.98 hr Mus musculus
T1/2 2.78 hr Mus musculus
T1/2 3.86 hr Rattus norvegicus
T1/2 5.42 hr Rattus norvegicus
T1/2 10.7 hr Canis lupus familiaris
T1/2 13.2 hr Canis lupus familiaris
Tmax 2.33 hr Mus musculus
Tmax 6.0 hr Rattus norvegicus
Tmax 3.0 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase SYK IC50 = 3.0 nM 8.52 Inhibition of recombinant human N-terminal His/GST-tagged SYK (356 to 635 residu... 38604095
Tyrosine-protein kinase SYK IC50 = 7.0 nM 8.15 Inhibition of SYK (unknown origin) 38604095
Syk protein IC50 = 27.0 nM 7.57 Inhibition of SYK in mouse BaF3-TEL/SYK cells in absence of IL-3 stimulation 38604095
BaF3 IC50 = 27.0 nM 7.57 Antiproliferative activity against mouse BaF3 cells harboring TEL/SYK incubated ... 38604095
Interferon-induced, double-stranded RNA-activated protein kinase IC50 = 79.0 nM 7.1 Inhibition of PKR (unknown origin) 38604095
Proto-oncogene tyrosine-protein kinase ROS IC50 = 110.0 nM 6.96 Inhibition of ROS1 (unknown origin) 38604095
Receptor-type tyrosine-protein kinase FLT3 IC50 = 182.0 nM 6.74 Inhibition of FLT3 (unknown origin) 38604095
Tyrosine-protein kinase ZAP-70 IC50 = 191.0 nM 6.72 Inhibition of ZAP70 (unknown origin) 38604095
Protein kinase C beta type IC50 = 239.0 nM 6.62 Inhibition of PKCbeta (unknown origin) 38604095
Muscle, skeletal receptor tyrosine-protein kinase IC50 = 257.0 nM 6.59 Inhibition of MUSK (unknown origin) 38604095
cAMP-dependent protein kinase catalytic subunit alpha IC50 = 450.0 nM 6.35 Inhibition of PKAalpha (unknown origin) 38604095
Platelet-derived growth factor receptor alpha IC50 = 567.0 nM 6.25 Inhibition of PDGFRalpha (unknown origin) 38604095
Unchecked IC50 = 628.0 nM 6.2 Inhibition of KIT V559D/D8167 mutant (unknown origin) 38604095
High affinity nerve growth factor receptor IC50 = 697.0 nM 6.16 Inhibition of TRKA (unknown origin) 38604095
SU-DHL-6 IC50 = 702.4 nM 6.15 Antiproliferative activity against human SU-DHL-6 cells incubated for 72 hrs by ... 38604095
Mitogen-activated protein kinase kinase kinase 3 IC50 = 738.0 nM 6.13 Inhibition of MAP3K3 (unknown origin) 38604095
Homeodomain-interacting protein kinase 1 IC50 = 798.0 nM 6.1 Inhibition of HIPK1 (unknown origin) 38604095
Tyrosine-protein kinase Fer IC50 = 802.0 nM 6.1 Inhibition of FER (unknown origin) 38604095
Tyrosine-protein kinase JAK2 IC50 = 980.0 nM 6.01 Inhibition of JAK2 (unknown origin) 38604095
Syk protein IC50 = 7827.0 nM 5.11 Inhibition of SYK in IL-3 stimulated mouse BaF3-TEL/SYK cells 38604095

Literature References

PubMed DOI Target Context # Activities
38604095 10.1016/j.ejmech.2024.116375 ADMET 39
38604095 10.1016/j.ejmech.2024.116375 Tyrosine-protein kinase SYK 4
38604095 10.1016/j.ejmech.2024.116375 Syk protein 3
38604095 10.1016/j.ejmech.2024.116375 BaF3 2
38604095 10.1016/j.ejmech.2024.116375 Unchecked 2
38604095 10.1016/j.ejmech.2024.116375 Interferon-induced, double-stranded RNA-activated protein kinase 1
38604095 10.1016/j.ejmech.2024.116375 Proto-oncogene tyrosine-protein kinase ROS 1
38604095 10.1016/j.ejmech.2024.116375 Receptor-type tyrosine-protein kinase FLT3 1
38604095 10.1016/j.ejmech.2024.116375 Tyrosine-protein kinase ZAP-70 1
38604095 10.1016/j.ejmech.2024.116375 Protein kinase C beta type 1
38604095 10.1016/j.ejmech.2024.116375 Muscle, skeletal receptor tyrosine-protein kinase 1
38604095 10.1016/j.ejmech.2024.116375 cAMP-dependent protein kinase catalytic subunit alpha 1
38604095 10.1016/j.ejmech.2024.116375 Platelet-derived growth factor receptor alpha 1
38604095 10.1016/j.ejmech.2024.116375 No relevant target 1
38604095 10.1016/j.ejmech.2024.116375 High affinity nerve growth factor receptor 1
38604095 10.1016/j.ejmech.2024.116375 Mitogen-activated protein kinase kinase kinase 3 1
38604095 10.1016/j.ejmech.2024.116375 Homeodomain-interacting protein kinase 1 1
38604095 10.1016/j.ejmech.2024.116375 Tyrosine-protein kinase Fer 1
38604095 10.1016/j.ejmech.2024.116375 Tyrosine-protein kinase JAK2 1
38604095 10.1016/j.ejmech.2024.116375 SU-DHL-6 1

Data from ChEMBL 36 via Core Engine