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Compound Detail

CHEMBL2386653

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C[C@@H](O)c1nc2cnc3[nH]ccc3c2n1[C@H]1CCCOC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2386653
Phase Preclinical
Structure Type MOL
InChI Key VSKQOMHTMYZRLK-ZJUUUORDSA-N
4
Targets
7
Activities
3
Assay Types
20
PK Parameters
20
Publications
0
Known Names

Molecular Properties

286.3
MW (Da)
2.32
ALogP
5
HBA
2
HBD
76.0
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 C15H18N4O2
MW 286.33
Aromatic Rings 3
Heavy Atoms 21
NP-Likeness -0.51

Activity Summary

Ki 4 meas. best 8.55
EC50 2 meas. best 6.96
IC50 1 meas. best 6.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase JAK1
CHEMBL2835
 Ki 8.55 8.545 2.8 2
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 Ki 7.51 7.51 31.0 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 Ki 6.96 6.96 110.0 1
Tyrosine-protein kinase JAK1
CHEMBL2835
 EC50 6.96 6.855 110.0 2
Janus Kinase (JAK)
CHEMBL2363062
 IC50 6.68 6.68 210.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1231.22 ng.hr.mL-1 Macaca fascicularis
AUC 18811.88 ng.hr.mL-1 Canis lupus familiaris
AUC 3063.73 ng.hr.mL-1 Rattus norvegicus
CL 19.0 mL.min-1.kg-1 Macaca fascicularis
CL 2.1 mL.min-1.kg-1 Canis lupus familiaris
CL 22.0 mL.min-1.kg-1 Rattus norvegicus
CL 21.0 mL.min-1.kg-1 Macaca mulatta
CL 4.9 mL.min-1.kg-1 Canis lupus familiaris
CL 2.3 mL.min-1.kg-1 Rattus norvegicus
CL 1.9 mL.min-1.kg-1 Homo sapiens
CL 2.0 mL.min-1.kg-1 Homo sapiens
Cmax 1800.0 nM Macaca fascicularis
Cmax 9800.0 nM Canis lupus familiaris
Cmax 5200.0 nM Rattus norvegicus
F 70.0 % Macaca fascicularis
F 111.0 % Canis lupus familiaris
F 197.0 % Rattus norvegicus
T1/2 1.1 hr Macaca fascicularis
T1/2 5.7 hr Canis lupus familiaris
T1/2 1.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase JAK1 Ki = 2.8 nM 8.55 Inhibition of recombinant JAK1 (unknown origin) using Val-Ala-Leu-Val-Asp-Gly-Ty... 23659214
Tyrosine-protein kinase JAK1 Ki = 2.9 nM 8.54 Inhibition of recombinant human JAK1 (854 to 1154 residues) expressed in insect ... 30981576
Non-receptor tyrosine-protein kinase TYK2 Ki = 31.0 nM 7.51 Inhibition of recombinant TYK2 (unknown origin) using Val-Ala-Leu-Val-Asp-Gly-Ty... 23659214
Tyrosine-protein kinase JAK1 EC50 = 110.0 nM 6.96 Inhibition of JAK1 in human TF1 cells assessed as inhibition of IL6-induced STAT... 23659214
Tyrosine-protein kinase JAK3 Ki = 110.0 nM 6.96 Inhibition of JAK3 (unknown origin) using Leu-Pro-Leu-Asp-Lys-Asp-Tyr-Tyr-Val-Va... 23659214
Tyrosine-protein kinase JAK1 EC50 = 180.0 nM 6.75 Inhibition of JAK1 in human TF1 cells assessed as inhibition of IL6-induced STAT... 23659214
Janus Kinase (JAK) IC50 = 210.0 nM 6.68 Inhibition of JAK in human BEAS-2B cells assessed as reduction in IL13-induced S... 30981576

Literature References

PubMed DOI Target Context # Activities
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 Rattus norvegicus 5
30981576 10.1016/j.bmcl.2019.04.008 Unchecked 4
23659214 10.1021/jm4004895 Cytochrome P450 3A4 3
23659214 10.1021/jm4004895 Plasma 3
30981576 10.1016/j.bmcl.2019.04.008 ADMET 2
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

Data from ChEMBL 36 via Core Engine