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Compound Detail

CHEMBL4753549

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Cc1cnc(Nc2ccc3c(c2)CCN(C(=O)/C=C/CN(C)C)C3)nc1-c1cnn(C(C)C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4753549
Phase Preclinical
Structure Type MOL
InChI Key SURRDPSGERGIIM-VOTSOKGWSA-N
9
Targets
18
Activities
1
Assay Types
20
PK Parameters
20
Publications
0
Known Names

Molecular Properties

459.6
MW (Da)
3.98
ALogP
7
HBA
1
HBD
79.2
PSA (Ų)
0.54
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H33N7O
MW 459.60
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -1.46

Activity Summary

IC50 18 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 8.52 7.8225 3.0 4
Tyrosine-protein kinase JAK2
CHEMBL1649049
 IC50 7.39 7.39 41.0 2
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 7.38 7.38 42.0 2
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 7.21 6.8267 62.0 3
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 IC50 7.12 7.12 75.0 2
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 7.03 7.03 94.0 2
Vero
CHEMBL391
 IC50 5.17 5.17 6750.0 1
Unchecked
CHEMBL612545
 IC50 5.16 5.16 6930.0 1
L02
CHEMBL4296457
 IC50 5.14 5.14 7220.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 253.6 ng.hr.mL-1 Rattus norvegicus
AUC 987.9 ng.hr.mL-1 Rattus norvegicus
AUC 253.6 ng.hr.mL-1 Rattus norvegicus
CL 423.33 mL.min-1.kg-1 Rattus norvegicus
CL 480.0 mL.min-1.kg-1 Rattus norvegicus
CL 83.5 mL.min-1.kg-1 Rattus norvegicus
CL 480.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 111.18 nM Rattus norvegicus
Cmax 1042.86 nM Rattus norvegicus
Cmax 111.18 nM Rattus norvegicus
F 25.7 % Rattus norvegicus
F 25.7 % Rattus norvegicus
T1/2 0.91 hr Rattus norvegicus
T1/2 1.8 hr Rattus norvegicus
T1/2 4.0 hr Rattus norvegicus
T1/2 0.91 hr Homo sapiens
T1/2 1.8 hr Rattus norvegicus
Tmax 0.9 hr Rattus norvegicus
Tmax 0.08 hr Rattus norvegicus
Tmax 0.9 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase JAK2 IC50 = 3.0 nM 8.52 Inhibition of JAK2 (unknown origin) in presence of Mg/ATP mixture by [gamma p33]... 37583815
Tyrosine-protein kinase JAK2 IC50 = 3.0 nM 8.52 Inhibition of recombinant human JAK2 (808 to end residues) KTFCGTPEYLAPEVRREPRIL... 33256400
Tyrosine-protein kinase JAK2 IC50 = 11.7 nM 7.93 Inhibition of JAK2 V617F mutant in human SET-2 cells assessed as reduction in ce... 33256400
Tyrosine-protein kinase JAK2 IC50 = 41.0 nM 7.39 Inhibition of JAK2 V617F mutant in mouse BaF3 cells assessed as reduction in cel... 33256400
Tyrosine-protein kinase JAK2 IC50 = 41.0 nM 7.39 Inhibition of JAK2 V617F mutant in mouse BaF3 cells 37583815
Tyrosine-protein kinase JAK1 IC50 = 42.0 nM 7.38 Inhibition of human JAK1 (866 to end residues) using GEEPLYWSFPAKKK as substrate... 33256400
Tyrosine-protein kinase JAK1 IC50 = 42.0 nM 7.38 Inhibition of JAK1 (unknown origin) in presence of Mg/ATP mixture by [gamma p33]... 37583815
Receptor-type tyrosine-protein kinase FLT3 IC50 = 62.0 nM 7.21 Inhibition of recombinant human FLT3 D835Y mutant (564 to end residues) using EA... 33256400
Receptor-type tyrosine-protein kinase FLT3 IC50 = 62.0 nM 7.21 Inhibition of FLT3 (unknown origin) in presence of Mg/ATP mixture by [gamma p33]... 37583815
Non-receptor tyrosine-protein kinase TYK2 IC50 = 75.0 nM 7.12 Inhibition of recombinant human TYK2 (875 to end residues) using GGMEDIYFEFMGGKK... 33256400
Non-receptor tyrosine-protein kinase TYK2 IC50 = 75.0 nM 7.12 Inhibition of TYK2 (unknown origin) in presence of Mg/ATP mixture by [gamma p33]... 37583815
Tyrosine-protein kinase JAK3 IC50 = 94.0 nM 7.03 Inhibition of recombinant human JAK3 (781 to end residues) using GGEEEEYFELVKKKK... 33256400
Tyrosine-protein kinase JAK3 IC50 = 94.0 nM 7.03 Inhibition of JAK3 (unknown origin) in presence of Mg/ATP mixture by [gamma p33]... 37583815
Tyrosine-protein kinase JAK2 IC50 = 475.3 nM 6.32 Inhibition of JAK2 V617F mutant in human SET2 cells 37583815
Receptor-type tyrosine-protein kinase FLT3 IC50 = 880.0 nM 6.06 Inhibition of FLT3 ITD mutant in human MOLM13 cells assessed as reduction in cel... 33256400
Vero IC50 = 6750.0 nM 5.17 Cytotoxicity against African green monkey Vero cells assessed as reduction in ce... 33256400
Unchecked IC50 = 6930.0 nM 5.16 Cytotoxicity against rat H9c2(2-1) cells assessed as reduction in cell viability... 33256400
L02 IC50 = 7220.0 nM 5.14 Cytotoxicity against human L02 cells assessed as reduction in cell viability inc... 33256400

Literature References

PubMed DOI Target Context # Activities
37583815 10.1021/acsmedchemlett.3c00251 BaF3 35
33256400 10.1021/acs.jmedchem.0c01488 SET-2 24
33256400 10.1021/acs.jmedchem.0c01488 ADMET 16
33256400 10.1021/acs.jmedchem.0c01488 Unchecked 7
37583815 10.1021/acsmedchemlett.3c00251 ADMET 7
33256400 10.1021/acs.jmedchem.0c01488 Tyrosine-protein kinase JAK2 6
33256400 10.1021/acs.jmedchem.0c01488 Receptor-type tyrosine-protein kinase FLT3 5
37583815 10.1021/acsmedchemlett.3c00251 Unchecked 4
37583815 10.1021/acsmedchemlett.3c00251 Tyrosine-protein kinase JAK2 4
33256400 10.1021/acs.jmedchem.0c01488 BaF3 4
33256400 10.1021/acs.jmedchem.0c01488 L02 1
33256400 10.1021/acs.jmedchem.0c01488 Signal transducer and activator of transcription 3 1
33256400 10.1021/acs.jmedchem.0c01488 Signal transducer and transcription activator 6 1
33256400 10.1021/acs.jmedchem.0c01488 Signal transducer and activator of transcription 1 1
33256400 10.1021/acs.jmedchem.0c01488 Vero 1
33256400 10.1021/acs.jmedchem.0c01488 Non-receptor tyrosine-protein kinase TYK2 1
37583815 10.1021/acsmedchemlett.3c00251 Tyrosine-protein kinase JAK1 1
37583815 10.1021/acsmedchemlett.3c00251 Tyrosine-protein kinase JAK3 1
37583815 10.1021/acsmedchemlett.3c00251 Non-receptor tyrosine-protein kinase TYK2 1
33256400 10.1021/acs.jmedchem.0c01488 Tyrosine-protein kinase JAK3 1

Data from ChEMBL 36 via Core Engine