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Compound Detail

CHEMBL1650951

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CC(C)(O)C(=O)N1CCN(c2ccc(C(F)(F)F)c(C3=C(c4c[nH]c5ccccc45)C(=O)NC3=O)c2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1650951
Phase Preclinical
Structure Type MOL
InChI Key CLGRAWDGLMENOD-UHFFFAOYSA-N
9
Targets
23
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

526.5
MW (Da)
3.17
ALogP
5
HBA
3
HBD
105.7
PSA (Ų)
0.45
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H25F3N4O4
MW 526.52
Aromatic Rings 3
Heavy Atoms 38
NP-Likeness -0.52

Activity Summary

IC50 21 meas. best 9.3
EC50 2 meas. best 5.98

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 9.3 8.04 0.5 8
Glycogen synthase kinase-3 beta
CHEMBL262
 IC50 8.52 8.52 3.0 1
Protein kinase C alpha type
CHEMBL299
 IC50 7.89 7.89 13.0 1
Protein kinase C theta type
CHEMBL3920
 IC50 7.17 7.17 68.0 1
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 6.51 6.32 311.0 3
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 6.24 5.915 578.0 2
Jurkat
CHEMBL397
 IC50 6.16 6.16 689.0 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 EC50 5.98 5.84 1042.0 2
Tyrosine-protein kinase JAK3
CHEMBL5250
 IC50 5.89 5.89 1294.0 1
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 IC50 5.77 5.5133 1691.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase JAK3 IC50 = 0.5 nM 9.3 Inhibition of JAK3 (unknown origin) 24461299
Tyrosine-protein kinase JAK3 IC50 = 1.0 nM 9.0 Inhibition of human JAK3 using GEEEEYFELVKKKK as substrate in presence of 10 uM ... 29852068
Tyrosine-protein kinase JAK3 IC50 = 1.5 nM 8.82 Inhibition of JAK3 (unknown origin) in presence of ATP by radiometric assay 27840070
Tyrosine-protein kinase JAK3 IC50 = 2.0 nM 8.7 Inhibition of human N-terminal His-tagged JAK3 (795 to 1124 residues) expressed ... 30615446
Glycogen synthase kinase-3 beta IC50 = 3.0 nM 8.52 Inhibition of GSK3-beta 21155605
Tyrosine-protein kinase JAK3 IC50 = 8.0 nM 8.1 Inhibition of GST-tagged Jak3 expressed in insect cells using 18 uM ATP 21155605
Tyrosine-protein kinase JAK3 IC50 = 11.0 nM 7.96 Inhibition of recombinant human JAK3 (781 to 1124 residues) expressed in baculov... 29852068
Protein kinase C alpha type IC50 = 13.0 nM 7.89 Inhibition of PKCalpha 21155605
Protein kinase C theta type IC50 = 68.0 nM 7.17 Inhibition of PKCtheta 21155605
Tyrosine-protein kinase JAK1 IC50 = 311.0 nM 6.51 Inhibition of JAK1 (unknown origin) 24461299
Tyrosine-protein kinase JAK1 IC50 = 344.0 nM 6.46 Inhibition of human JAK1 using poly[Glu:Tyr] (4:1) as substrate in presence of 1... 29852068
Tyrosine-protein kinase JAK3 IC50 = 525.0 nM 6.28 Inhibition of Jak3-mediated IL15-induced Stat5 phosphorylation in human MO7 cell... 21155605
Tyrosine-protein kinase JAK2 IC50 = 578.0 nM 6.24 Inhibition of human JAK2 using poly[Glu:Tyr] (4:1) as substrate in presence of 1... 29852068
Tyrosine-protein kinase JAK3 IC50 = 685.0 nM 6.16 Inhibition of human N-terminal His-tagged JAK3 (795 to 1124 residues) expressed ... 30615446
Jurkat IC50 = 689.0 nM 6.16 Inhibition of antiTCR/antiCD28-stimulated IL2 production in human Jurkat cells b... 21155605
Tyrosine-protein kinase JAK1 IC50 = 1017.0 nM 5.99 Inhibition of GST-tagged Jak1 expressed in insect cells using 70 uM ATP 21155605
Tyrosine-protein kinase JAK3 EC50 = 1042.0 nM 5.98 Inhibition of JAK3 in human CTLL2 cells assessed as reduction in IL15-induced ST... 30615446
Tyrosine-protein kinase JAK3 IC50 = 1294.0 nM 5.89 Inhibition of Jak3-mediated IL2-induced Stat5 phosphorylation in mouse CTLL cell... 21155605
Non-receptor tyrosine-protein kinase TYK2 IC50 = 1691.0 nM 5.77 Inhibition of TYK2 (unknown origin) 24461299
Tyrosine-protein kinase JAK3 EC50 = 1999.0 nM 5.7 Inhibition of JAK3 in human CTLL2 cells assessed as reduction in IL2-induced STA... 30615446

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 Fibroblast 304
- 10.6019/CHEMBL5058577 U2OS 304
- 10.6019/CHEMBL5058577 Fibroblast 304
- 10.6019/CHEMBL5058577 HEK-293T 304
- 10.6019/CHEMBL5724801 U2OS 304
- 10.6019/CHEMBL5724801 HEK-293T 304
- 10.6019/CHEMBL5058564 Fibroblast 10
- 10.6019/CHEMBL5058564 U2OS 10
- 10.6019/CHEMBL5058564 HEK-293T 9
30615446 10.1021/acs.jmedchem.8b01823 Tyrosine-protein kinase JAK3 8
- 10.6019/CHEMBL5303304 HEK-293T 8
- 10.6019/CHEMBL5303304 U2OS 6
- 10.6019/CHEMBL5303304 Fibroblast 5
21155605 10.1021/jm101157q Jurkat 5
21155605 10.1021/jm101157q CTLL 4
27840070 10.1016/j.chembiol.2016.10.008 Unchecked 3
21155605 10.1021/jm101157q Tyrosine-protein kinase JAK3 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
29852068 10.1021/acs.jmedchem.8b00571 Tyrosine-protein kinase JAK3 2

Data from ChEMBL 36 via Core Engine