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Compound Detail

CHEMBL2386635

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

Basic Information

ChEMBL ID CHEMBL2386635
Phase Preclinical
Structure Type MOL
InChI Key IKSRDHMMQOCRHN-JHJVBQTASA-N
5
Targets
17
Activities
3
Assay Types
15
PK Parameters
18
Publications
0
Known Names

Molecular Properties

323.4
MW (Da)
3.61
ALogP
5
HBA
2
HBD
90.5
PSA (Ų)
0.77
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H21N5O
MW 323.40
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -0.55

Activity Summary

EC50 7 meas. best 9.47
IC50 7 meas. best 9.7
Ki 3 meas. best 10.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase JAK1
CHEMBL2835
 Ki 10.0 10.0 0.1 1
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 IC50 9.7 9.7 0.2 2
Tyrosine-protein kinase JAK1
CHEMBL2835
 EC50 9.47 8.42 0.3 3
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 Ki 9.4 9.4 0.4 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 9.22 9.22 0.6 2
Tyrosine-protein kinase JAK2
CHEMBL2971
 EC50 8.48 8.48 3.3 1
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 EC50 8.48 7.74 3.3 2
Tyrosine-protein kinase JAK3
CHEMBL2148
 Ki 8.23 8.23 5.9 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 EC50 7.88 7.88 13.1 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 7.3 7.3 49.7 2
Cytochrome P450 3A4
CHEMBL340
 IC50 5.06 5.06 8800.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3622.08 ng.hr.mL-1 Canis lupus familiaris
AUC 420.42 ng.hr.mL-1 Rattus norvegicus
CL 17.0 mL.min-1.kg-1 Canis lupus familiaris
CL 38.0 mL.min-1.kg-1 Rattus norvegicus
CL 25.0 mL.min-1.kg-1 Macaca mulatta
CL 12.0 mL.min-1.kg-1 Canis lupus familiaris
CL 15.0 mL.min-1.kg-1 Rattus norvegicus
CL 6.8 mL.min-1.kg-1 Homo sapiens
CL 5.2 mL.min-1.kg-1 Homo sapiens
Cmax 2500.0 nM Canis lupus familiaris
Cmax 930.0 nM Rattus norvegicus
F 183.0 % Canis lupus familiaris
F 49.0 % Rattus norvegicus
T1/2 1.8 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 = 0.1 nM 10.0 Inhibition of recombinant JAK1 (unknown origin) using Val-Ala-Leu-Val-Asp-Gly-Ty... 23659214
Non-receptor tyrosine-protein kinase TYK2 IC50 = 0.2 nM 9.7 Enzymatic Inhibition Assay: 11-point dosing series were made for each compound b... -
Non-receptor tyrosine-protein kinase TYK2 IC50 = 0.2 nM 9.7 Enzymatic Inhibition Assay: 11-point dosing series were made for each compound b... -
Tyrosine-protein kinase JAK1 EC50 = 0.34 nM 9.47 Kinase Assay: Human baculovirus-expressed Janus kinase (JAK) 1, 2, 3 and tyrosin... -
Non-receptor tyrosine-protein kinase TYK2 Ki = 0.4 nM 9.4 Inhibition of recombinant TYK2 (unknown origin) using Val-Ala-Leu-Val-Asp-Gly-Ty... 23659214
Tyrosine-protein kinase JAK2 IC50 = 0.6 nM 9.22 Enzymatic Inhibition Assay: 11-point dosing series were made for each compound b... -
Tyrosine-protein kinase JAK2 IC50 = 0.6 nM 9.22 Enzymatic Inhibition Assay: 11-point dosing series were made for each compound b... -
Tyrosine-protein kinase JAK2 EC50 = 3.34 nM 8.48 Kinase Assay: Human baculovirus-expressed Janus kinase (JAK) 1, 2, 3 and tyrosin... -
Non-receptor tyrosine-protein kinase TYK2 EC50 = 3.32 nM 8.48 Kinase Assay: Human baculovirus-expressed Janus kinase (JAK) 1, 2, 3 and tyrosin... -
Tyrosine-protein kinase JAK1 EC50 = 5.7 nM 8.24 Inhibition of JAK1 in human TF1 cells assessed as inhibition of IL6-induced STAT... 23659214
Tyrosine-protein kinase JAK3 Ki = 5.9 nM 8.23 Inhibition of JAK3 (unknown origin) using Leu-Pro-Leu-Asp-Lys-Asp-Tyr-Tyr-Val-Va... 23659214
Tyrosine-protein kinase JAK3 EC50 = 13.1 nM 7.88 Kinase Assay: Human baculovirus-expressed Janus kinase (JAK) 1, 2, 3 and tyrosin... -
Tyrosine-protein kinase JAK1 EC50 = 28.0 nM 7.55 Inhibition of JAK1 in human TF1 cells assessed as inhibition of IL6-induced STAT... 23659214
Tyrosine-protein kinase JAK3 IC50 = 49.7 nM 7.3 Enzymatic Inhibition Assay: 11-point dosing series were made for each compound b... -
Tyrosine-protein kinase JAK3 IC50 = 49.7 nM 7.3 Enzymatic Inhibition Assay: 11-point dosing series were made for each compound b... -
Non-receptor tyrosine-protein kinase TYK2 EC50 = 100.0 nM 7.0 Inhibition of TYK2 in human NK92 cells assessed as inhibition of IL12-induced ST... 23659214
Cytochrome P450 3A4 IC50 = 8800.0 nM 5.06 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 5
23659214 10.1021/jm4004895 Tyrosine-protein kinase JAK1 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