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Compound Detail

CHEMBL2325895

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CC(C)(C)[C@@H](NC(=O)c1c[nH]c2ncc(C3CC3)nc12)C(=O)N1CC(C#N)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2325895
Phase Preclinical
Structure Type MOL
InChI Key SIEMFXMJGAMFQR-INIZCTEOSA-N
11
Targets
24
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

380.4
MW (Da)
1.96
ALogP
5
HBA
2
HBD
114.8
PSA (Ų)
0.84
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H24N6O2
MW 380.45
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.60

Activity Summary

IC50 20 meas. best 9.59
Kd 4 meas. best 9.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase JAK3
CHEMBL2148
 Kd 9.92 9.92 0.1 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 Kd 9.74 9.74 0.2 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 9.59 9.5433 0.3 3
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 9.1 7.9125 0.8 4
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 8.49 8.49 3.2 2
Tyrosine-protein kinase JAK1
CHEMBL2835
 Kd 7.92 7.92 12.0 1
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 Kd 7.8 7.8 16.0 1
JAK3/JAK1
CHEMBL3038491
 IC50 7.51 7.0067 31.0 3
Tyrosine-protein kinase JAK1/JAK2
CHEMBL3885649
 IC50 6.77 6.77 170.0 1
Tyrosine-protein kinase JAK1/JAK3
CHEMBL3885650
 IC50 6.75 6.75 180.0 1
JAK2/JAK1
CHEMBL3038492
 IC50 6.54 6.54 290.0 2
JAK1/JAK2/TYK2
CHEMBL3301390
 IC50 6.06 5.99 864.0 2
Tyrosine-protein kinase JAK2
CHEMBL1649049
 IC50 5.96 5.96 1100.0 1
TYK2/JAK1/JAK2
CHEMBL3885642
 IC50 5.0 5.0 9900.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1195.0 ng.hr.mL-1 Rattus norvegicus
CL 14.6 ml/kg.min Rattus norvegicus
Cmax 1046.13 nM Rattus norvegicus
F 25.0 % Rattus norvegicus
Fu 0.034 - Homo sapiens
T1/2 3.8 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase JAK3 Kd = 0.12 nM 9.92 Binding affinity to JAK3 (unknown origin) 23214979
Tyrosine-protein kinase JAK2 Kd = 0.18 nM 9.74 Binding affinity to JAK2 (unknown origin) 23214979
Tyrosine-protein kinase JAK3 IC50 = 0.26 nM 9.59 Inhibition of JAK3 (unknown origin)-mediated phosphorylation of Biotin-KAIETDKEY... 23214979
Tyrosine-protein kinase JAK3 IC50 = 0.3 nM 9.52 Inhibition of JAK3 (unknown origin) using [33gammaP]ATP and Biotin-KAIETDKEYYTVK... 23540648
Tyrosine-protein kinase JAK3 IC50 = 0.3 nM 9.52 Inhibition of JAK3 (unknown origin) in presence of ATP by radiometric assay 27840070
Tyrosine-protein kinase JAK2 IC50 = 0.8 nM 9.1 Inhibition of JAK2 (unknown origin)-mediated phosphorylation of Biotin-KAIETDKEY... 23214979
Tyrosine-protein kinase JAK2 IC50 = 0.8 nM 9.1 Inhibition of JAK2 (unknown origin) using [33gammaP]ATP and Biotin-KAIETDKEYYTVK... 23540648
Tyrosine-protein kinase JAK1 IC50 = 3.2 nM 8.49 Inhibition of JAK1 (unknown origin)-mediated phosphorylation of Biotin-KAIETDKEY... 23214979
Tyrosine-protein kinase JAK1 IC50 = 3.2 nM 8.49 Inhibition of JAK1 (unknown origin) using [33gammaP]ATP and Biotin-KAIETDKEYYTVK... 23540648
Tyrosine-protein kinase JAK1 Kd = 12.0 nM 7.92 Binding affinity to JAK1 (unknown origin) 23214979
Non-receptor tyrosine-protein kinase TYK2 Kd = 16.0 nM 7.8 Binding affinity to TYK2 (unknown origin) 23214979
JAK3/JAK1 IC50 = 31.0 nM 7.51 Inhibition of JAK3/1 in human T cells expressing CD3 assessed as inhibition of I... 23540648
JAK3/JAK1 IC50 = 31.0 nM 7.51 Inhibition of JAK3/JAK1 in human PBMC expressing CD3 assessed as inhibition of I... 23214979
Tyrosine-protein kinase JAK1/JAK2 IC50 = 170.0 nM 6.77 Inhibition of JAK2/JAK1 in C57BL/6 mouse whole blood assessed as inhibition of I... 23214979
Tyrosine-protein kinase JAK1/JAK3 IC50 = 180.0 nM 6.75 Inhibition of JAK3/JAK1 in C57BL/6 mouse whole blood assessed as inhibition of I... 23214979
Tyrosine-protein kinase JAK2 IC50 = 188.0 nM 6.73 Inhibition of JAK2 in human PBMC expressing CD14 assessed as inhibition of GM-CS... 23214979
Tyrosine-protein kinase JAK2 IC50 = 190.0 nM 6.72 Inhibition of JAK2 in human monocytes expressing CD14 assessed as inhibition of ... 23540648
JAK2/JAK1 IC50 = 291.0 nM 6.54 Inhibition of JAK2/JAK1 in human PBMC expressing CD14 assessed as inhibition of ... 23214979
JAK2/JAK1 IC50 = 290.0 nM 6.54 Inhibition of JAK2/1 in human T cells expressing CD3 assessed as inhibition of I... 23540648
JAK1/JAK2/TYK2 IC50 = 864.0 nM 6.06 Inhibition of JAK1/JAK2/TYK2 in human PBMC expressing CD14 assessed as inhibitio... 23214979

Literature References

PubMed DOI Target Context # Activities
23214979 10.1021/jm301646k Unchecked 7
23214979 10.1021/jm301646k Rattus norvegicus 6
23214979 10.1021/jm301646k Mus musculus 5
23540648 10.1016/j.bmcl.2013.02.012 Unchecked 4
23214979 10.1021/jm301646k Tyrosine-protein kinase JAK2 4
27840070 10.1016/j.chembiol.2016.10.008 Unchecked 3
23214979 10.1021/jm301646k NON-PROTEIN TARGET 2
23540648 10.1016/j.bmcl.2013.02.012 Tyrosine-protein kinase JAK2 2
23214979 10.1021/jm301646k Tyrosine-protein kinase JAK1 2
23214979 10.1021/jm301646k Tyrosine-protein kinase JAK3 2
23214979 10.1021/jm301646k JAK1/JAK2/TYK2 2
23214979 10.1021/jm301646k Liver microsomes 2
23214979 10.1021/jm301646k Caco-2 2
23214979 10.1021/jm301646k JAK3/JAK1 2
27840070 10.1016/j.chembiol.2016.10.008 Serine/threonine-protein kinase MARK1 1
23214979 10.1021/jm301646k Tyrosine-protein kinase SYK 1
23214979 10.1021/jm301646k JAK2/JAK1 1
23214979 10.1021/jm301646k Plasma 1
23214979 10.1021/jm301646k Tyrosine-protein kinase JAK1/JAK2 1
23214979 10.1021/jm301646k Non-receptor tyrosine-protein kinase TYK2 1

Data from ChEMBL 36 via Core Engine