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Compound Detail

CHEMBL447183

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N#Cc1ccc(C(=O)N2CCC3(CC2)N=C(N)c2c(F)ccc(F)c2N3)cn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL447183
Phase Preclinical
Structure Type MOL
InChI Key GIZYIOOBBUHOBS-UHFFFAOYSA-N
4
Targets
16
Activities
1
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

382.4
MW (Da)
1.99
ALogP
6
HBA
2
HBD
107.4
PSA (Ų)
0.78
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H16F2N6O
MW 382.37
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -1.34

Activity Summary

IC50 16 meas. best 7.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Nitric oxide synthase, inducible
CHEMBL4481
 IC50 7.46 6.96 35.0 9
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 7.0 7.0 100.0 1
Nitric oxide synthase 1
CHEMBL3568
 IC50 6.13 6.088 740.0 5
DLD-1
CHEMBL614285
 IC50 6.05 6.05 900.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 57.0 mL.min-1.kg-1 Rattus norvegicus
F 75.0 % Rattus norvegicus
T1/2 1.1 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Nitric oxide synthase, inducible IC50 = 35.0 nM 7.46 Inhibition of human iNOS 18849972
Nitric oxide synthase, inducible IC50 = 37.0 nM 7.43 In vitro inhibition of human Inducible nitric oxide synthase. 15163211
Nitric oxide synthase, inducible IC50 = 37.0 nM 7.43 Inhibitory activity of compound against human inducible nitric oxide synthase 12620067
Nitric oxide synthase, inducible IC50 = 37.15 nM 7.43 Inhibition of human iNOS assessed as inhibition of [3H]L-arginine to [3H]L-citru... 21684157
Nitric oxide synthase, inducible IC50 = 41.0 nM 7.39 Inhibition of human recombinant iNOS 21398123
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 100.0 nM 7.0 Inhibition of human ERG 21398123
Nitric oxide synthase, inducible IC50 = 170.0 nM 6.77 Inhibition of human iNOS expressed in human DLD1 cells after 1 hr 18024030
Nitric oxide synthase, inducible IC50 = 210.0 nM 6.68 Inhibition of cytokine-induced iNOS activity in human DLD1 cells after 24 hrs 18024030
Nitric oxide synthase 1 IC50 = 740.0 nM 6.13 In vitro inhibition of human neuronal nitric oxide synthase. 15163211
Nitric oxide synthase 1 IC50 = 741.31 nM 6.13 Inhibition of human nNOS assessed as inhibition of [3H]L-arginine to [3H]L-citru... 21684157
Nitric oxide synthase 1 IC50 = 790.0 nM 6.1 Inhibition of human nNOS 18849972
Nitric oxide synthase 1 IC50 = 840.0 nM 6.08 Inhibition of human nNOS expressed in insect SF9 cells after 1 hr 18024030
DLD-1 IC50 = 900.0 nM 6.05 Inhibitory activity against synthesis of inducible nitric oxide synthase by DLD-... 12620067
Nitric oxide synthase, inducible IC50 = 900.0 nM 6.05 Inhibition of human iNOS by whole cell assay 18849972
Nitric oxide synthase 1 IC50 = 1000.0 nM 6.0 Inhibitory activity against human neuronal nitric oxide synthase 12620067
Nitric oxide synthase, inducible IC50 = 1000.0 nM 6.0 Inhibition of iNOS in intact human DLD1 cells assessed as nitric oxide productio... 21398123

Literature References

PubMed DOI Target Context # Activities
21398123 10.1016/j.bmcl.2011.02.061 Rattus norvegicus 4
15163211 10.1021/jm031035n Nitric oxide synthase 3 2
21398123 10.1016/j.bmcl.2011.02.061 Hepatocyte 2
18849972 10.1038/nchembio.115 Unchecked 2
18849972 10.1038/nchembio.115 Nitric oxide synthase, inducible 2
21398123 10.1016/j.bmcl.2011.02.061 Nitric oxide synthase, inducible 2
- 10.6019/CHEMBL3301361 No relevant target 2
18024030 10.1016/j.bmcl.2007.10.073 Nitric oxide synthase, inducible 2
12620067 10.1021/jm0255926 Rattus norvegicus 2
12620067 10.1021/jm0255926 DLD-1 1
18024030 10.1016/j.bmcl.2007.10.073 Unchecked 1
18024030 10.1016/j.bmcl.2007.10.073 Nitric oxide sythases; iNOS & nNOS 1
18024030 10.1016/j.bmcl.2007.10.073 Nitric oxide synthase 3 1
18849972 10.1038/nchembio.115 Nitric oxide synthase 1 1
12620067 10.1021/jm0255926 Nitric oxide synthase 1 1
12620067 10.1021/jm0255926 Nitric oxide synthase 3 1
12620067 10.1021/jm0255926 Nitric oxide synthase, inducible 1
18849972 10.1038/nchembio.115 Nitric oxide sythases; iNOS & nNOS 1
18849972 10.1038/nchembio.115 Rattus norvegicus 1
15163211 10.1021/jm031035n Nitric oxide synthase 1 1

Data from ChEMBL 36 via Core Engine