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Compound Detail

CHEMBL2386636

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C[C@@H](O)c1nc2cnc3[nH]ccc3c2n1[C@H]1CC[C@H](CCC#N)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2386636
Phase Preclinical
Structure Type MOL
InChI Key LLRNGFSFYHDPKW-MGPQQGTHSA-N
5
Targets
8
Activities
3
Assay Types
20
PK Parameters
19
Publications
0
Known Names

Molecular Properties

337.4
MW (Da)
4.00
ALogP
5
HBA
2
HBD
90.5
PSA (Ų)
0.75
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 C19H23N5O
MW 337.43
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -0.61

Activity Summary

EC50 3 meas. best 7.48
Ki 3 meas. best 9.52
IC50 2 meas. best 5.17

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase JAK1
CHEMBL2835
 Ki 9.52 9.52 0.3 1
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 Ki 8.77 8.77 1.7 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 Ki 8.11 8.11 7.8 1
Tyrosine-protein kinase JAK1
CHEMBL2835
 EC50 7.48 7.425 33.0 2
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 EC50 6.01 6.01 980.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.17 5.17 6700.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.7 4.7 20000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 87.73 ng.hr.mL-1 Macaca fascicularis
AUC 1450.95 ng.hr.mL-1 Canis lupus familiaris
AUC 141.72 ng.hr.mL-1 Rattus norvegicus
CL 29.0 mL.min-1.kg-1 Macaca fascicularis
CL 29.0 mL.min-1.kg-1 Canis lupus familiaris
CL 126.0 mL.min-1.kg-1 Rattus norvegicus
CL 36.0 mL.min-1.kg-1 Macaca mulatta
CL 11.0 mL.min-1.kg-1 Canis lupus familiaris
CL 28.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.7 mL.min-1.kg-1 Homo sapiens
CL 5.2 mL.min-1.kg-1 Homo sapiens
Cmax 70.0 nM Macaca fascicularis
Cmax 1300.0 nM Canis lupus familiaris
Cmax 220.0 nM Rattus norvegicus
F 8.0 % Macaca fascicularis
F 125.0 % Canis lupus familiaris
F 50.0 % Rattus norvegicus
T1/2 0.8 hr Macaca fascicularis
T1/2 1.3 hr Canis lupus familiaris
T1/2 0.6 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase JAK1 Ki = 0.3 nM 9.52 Inhibition of recombinant JAK1 (unknown origin) using Val-Ala-Leu-Val-Asp-Gly-Ty... 23659214
Non-receptor tyrosine-protein kinase TYK2 Ki = 1.7 nM 8.77 Inhibition of recombinant TYK2 (unknown origin) using Val-Ala-Leu-Val-Asp-Gly-Ty... 23659214
Tyrosine-protein kinase JAK3 Ki = 7.8 nM 8.11 Inhibition of JAK3 (unknown origin) using Leu-Pro-Leu-Asp-Lys-Asp-Tyr-Tyr-Val-Va... 23659214
Tyrosine-protein kinase JAK1 EC50 = 33.0 nM 7.48 Inhibition of JAK1 in human TF1 cells assessed as inhibition of IL6-induced STAT... 23659214
Tyrosine-protein kinase JAK1 EC50 = 43.0 nM 7.37 Inhibition of JAK1 in human TF1 cells assessed as inhibition of IL6-induced STAT... 23659214
Non-receptor tyrosine-protein kinase TYK2 EC50 = 980.0 nM 6.01 Inhibition of TYK2 in human NK92 cells assessed as inhibition of IL12-induced ST... 23659214
Cytochrome P450 3A4 IC50 = 6700.0 nM 5.17 Reversible inhibition of CYP3A4 in human liver microsomes using midazolam as sub... 23659214
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 20000.0 nM 4.7 Inhibition of human ERG channel expressed in HEK293 cells by patch clamp assay 23659214

Literature References

PubMed DOI Target Context # Activities
23659214 10.1021/jm4004895 Rattus norvegicus 5
23659214 10.1021/jm4004895 Tyrosine-protein kinase JAK1 5
23659214 10.1021/jm4004895 Cynomolgus monkey 5
23659214 10.1021/jm4004895 Canis familiaris 5
23659214 10.1021/jm4004895 Cytochrome P450 3A4 3
23659214 10.1021/jm4004895 Plasma 3
23659214 10.1021/jm4004895 Unchecked 2
23659214 10.1021/jm4004895 No relevant target 2
23659214 10.1021/jm4004895 MDCK 2
23659214 10.1021/jm4004895 Hepatocyte 2
23659214 10.1021/jm4004895 ADMET 2
23659214 10.1021/jm4004895 Non-receptor tyrosine-protein kinase TYK2 2
23659214 10.1021/jm4004895 Cytochrome P450 2C9 2
23659214 10.1021/jm4004895 Cytochrome P450 2D6 2
23659214 10.1021/jm4004895 Cytochrome P450 2C19 2
23659214 10.1021/jm4004895 Cytochrome P450 1A2 2
23659214 10.1021/jm4004895 Tyrosine-protein kinase JAK3 1
23659214 10.1021/jm4004895 Voltage-gated inwardly rectifying potassium channel KCNH2 1
23659214 10.1021/jm4004895 Liver microsomes 1

Data from ChEMBL 36 via Core Engine