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Compound Detail

CHEMBL2386633

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

Basic Information

ChEMBL ID CHEMBL2386633
Phase Preclinical
Structure Type MOL
InChI Key ANDWOIMHOOWCLK-IJLUTSLNSA-N
4
Targets
7
Activities
3
Assay Types
26
PK Parameters
20
Publications
0
Known Names

Molecular Properties

309.4
MW (Da)
3.22
ALogP
5
HBA
2
HBD
90.5
PSA (Ų)
0.76
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H19N5O
MW 309.37
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -0.79

Activity Summary

EC50 3 meas. best 6.92
Ki 3 meas. best 8.72
IC50 1 meas. best 5.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase JAK1
CHEMBL2835
 Ki 8.72 8.72 1.9 1
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 Ki 7.92 7.92 12.0 1
Tyrosine-protein kinase JAK1
CHEMBL2835
 EC50 6.92 6.905 120.0 2
Tyrosine-protein kinase JAK3
CHEMBL2148
 Ki 6.55 6.55 280.0 1
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 EC50 5.25 5.25 5600.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.1 5.1 7900.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 83220.53 ng.hr.mL-1 Rattus norvegicus
AUC 15499.44 ng.hr.mL-1 Rattus norvegicus
AUC 3279.32 ng.hr.mL-1 Rattus norvegicus
AUC 144475.79 ng.hr.mL-1 Rattus norvegicus
AUC 18438.45 ng.hr.mL-1 Rattus norvegicus
AUC 4640.55 ng.hr.mL-1 Rattus norvegicus
AUC 1206.54 ng.hr.mL-1 Macaca fascicularis
AUC 2567.77 ng.hr.mL-1 Canis lupus familiaris
AUC 290.81 ng.hr.mL-1 Rattus norvegicus
CL 18.0 mL.min-1.kg-1 Macaca fascicularis
CL 16.0 mL.min-1.kg-1 Canis lupus familiaris
CL 60.0 mL.min-1.kg-1 Rattus norvegicus
CL 2.4 mL.min-1.kg-1 Macaca mulatta
CL 3.0 mL.min-1.kg-1 Canis lupus familiaris
CL 3.7 mL.min-1.kg-1 Rattus norvegicus
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 3.3 mL.min-1.kg-1 Homo sapiens
Cmax 630.0 nM Macaca fascicularis
Cmax 2100.0 nM Canis lupus familiaris
Cmax 420.0 nM Rattus norvegicus
F 65.0 % Macaca fascicularis
F 119.0 % Canis lupus familiaris
F 52.0 % Rattus norvegicus
T1/2 1.7 hr Macaca fascicularis
T1/2 2.2 hr Canis lupus familiaris
T1/2 0.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase JAK1 Ki = 1.9 nM 8.72 Inhibition of recombinant JAK1 (unknown origin) using Val-Ala-Leu-Val-Asp-Gly-Ty... 23659214
Non-receptor tyrosine-protein kinase TYK2 Ki = 12.0 nM 7.92 Inhibition of recombinant TYK2 (unknown origin) using Val-Ala-Leu-Val-Asp-Gly-Ty... 23659214
Tyrosine-protein kinase JAK1 EC50 = 120.0 nM 6.92 Inhibition of JAK1 in human TF1 cells assessed as inhibition of IL6-induced STAT... 23659214
Tyrosine-protein kinase JAK1 EC50 = 130.0 nM 6.89 Inhibition of JAK1 in human TF1 cells assessed as inhibition of IL6-induced STAT... 23659214
Tyrosine-protein kinase JAK3 Ki = 280.0 nM 6.55 Inhibition of JAK3 (unknown origin) using Leu-Pro-Leu-Asp-Lys-Asp-Tyr-Tyr-Val-Va... 23659214
Non-receptor tyrosine-protein kinase TYK2 EC50 = 5600.0 nM 5.25 Inhibition of TYK2 in human NK92 cells assessed as inhibition of IL12-induced ST... 23659214
Cytochrome P450 3A4 IC50 = 7900.0 nM 5.1 Reversible inhibition of CYP3A4 in human liver microsomes using midazolam as sub... 23659214

Literature References

PubMed DOI Target Context # Activities
23659214 10.1021/jm4004895 Rattus norvegicus 14
23659214 10.1021/jm4004895 Canis familiaris 5
23659214 10.1021/jm4004895 Cynomolgus monkey 5
23659214 10.1021/jm4004895 Tyrosine-protein kinase JAK1 5
23659214 10.1021/jm4004895 Cytochrome P450 3A4 3
23659214 10.1021/jm4004895 Plasma 3
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 ADMET 2
23659214 10.1021/jm4004895 Hepatocyte 2
23659214 10.1021/jm4004895 Cytochrome P450 1A2 2
23659214 10.1021/jm4004895 MDCK 2
23659214 10.1021/jm4004895 No relevant target 2
23659214 10.1021/jm4004895 Unchecked 2
23659214 10.1021/jm4004895 Voltage-gated inwardly rectifying potassium channel KCNH2 1
23659214 10.1021/jm4004895 Tyrosine-protein kinase JAK3 1
23659214 10.1021/jm4004895 Platelet-derived growth factor receptor alpha 1
23659214 10.1021/jm4004895 Liver microsomes 1

Data from ChEMBL 36 via Core Engine