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Compound Detail

CHEMBL1801160

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O=C(NC1CC1)c1cn(-c2cccc(-c3ccc([C@@H]4C[C@H]4C(=O)O)c(F)c3)c2)c2ncccc2c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1801160
Phase Preclinical
Structure Type MOL
InChI Key PSYPBAHXIIVDCJ-FCHUYYIVSA-N
5
Targets
8
Activities
1
Assay Types
12
PK Parameters
19
Publications
0
Known Names

Molecular Properties

483.5
MW (Da)
4.27
ALogP
5
HBA
2
HBD
101.3
PSA (Ų)
0.43
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H22FN3O4
MW 483.50
Aromatic Rings 4
Heavy Atoms 36
NP-Likeness -1.12

Activity Summary

IC50 8 meas. best 9.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 9.28 9.28 0.5 1
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 9.28 9.28 0.5 1
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 9.28 9.28 0.5 1
Phosphodiesterase 4
CHEMBL2093863
 IC50 9.22 7.74 0.6 2
Unchecked
CHEMBL612545
 IC50 7.28 6.5533 52.0 3

Pharmacokinetic Data

Parameter Value Units Species
CL 1.0 mL.min-1.kg-1 Rattus norvegicus
CL 1.7 mL.min-1.kg-1 Saimiri
CL 1.3 mL.min-1.kg-1 Macaca mulatta
CL 3.7 mL.min-1.kg-1 Canis lupus familiaris
F 38.0 % Rattus norvegicus
F 41.0 % Saimiri
F 77.0 % Macaca mulatta
F 100.0 % Canis lupus familiaris
T1/2 3.5 hr Rattus norvegicus
T1/2 4.3 hr Saimiri
T1/2 6.5 hr Macaca mulatta
T1/2 6.6 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 0.53 nM 9.28 Inhibition of PDE4A 20933411
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.53 nM 9.28 Inhibition of PDE4B 20933411
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.53 nM 9.28 Inhibition of PDE4D 20933411
Phosphodiesterase 4 IC50 = 0.6 nM 9.22 Inhibition of PDE4 (unknown origin) 32255344
Unchecked IC50 = 52.0 nM 7.28 Inhibition of PDE4 activity in squirrel monkey whole blood assessed as inhibitio... 20933411
Unchecked IC50 = 450.0 nM 6.35 Inhibition of PDE4 activity in rat whole blood assessed as inhibition of LPS-ind... 20933411
Phosphodiesterase 4 IC50 = 550.0 nM 6.26 Inhibition of PDE4 activity in human whole blood assessed as inhibition of LPS-i... 20933411
Unchecked IC50 = 940.0 nM 6.03 Inhibition of PDE4 activity in rhesus monkey whole blood assessed as inhibition ... 20933411

Literature References

PubMed DOI Target Context # Activities
20933411 10.1016/j.bmcl.2010.09.087 Rattus norvegicus 8
20933411 10.1016/j.bmcl.2010.09.087 Unchecked 4
20933411 10.1016/j.bmcl.2010.09.087 Hepatocyte 4
20933411 10.1016/j.bmcl.2010.09.087 Nucleic Acid 3
20933411 10.1016/j.bmcl.2010.09.087 Saimiri 3
20933411 10.1016/j.bmcl.2010.09.087 Rhesus monkey 3
20933411 10.1016/j.bmcl.2010.09.087 Canis familiaris 3
20933411 10.1016/j.bmcl.2010.09.087 ADMET 3
20933411 10.1016/j.bmcl.2010.09.087 Brain 2
20933411 10.1016/j.bmcl.2010.09.087 Plasma 2
32255344 10.1021/acs.jmedchem.9b02170 Phosphodiesterase 4 1
20933411 10.1016/j.bmcl.2010.09.087 3',5'-cyclic-AMP phosphodiesterase 4A 1
20933411 10.1016/j.bmcl.2010.09.087 Cytochrome P450 1A2 1
20933411 10.1016/j.bmcl.2010.09.087 Cytochrome P450 2D6 1
20933411 10.1016/j.bmcl.2010.09.087 Cytochrome P450 3A 1
20933411 10.1016/j.bmcl.2010.09.087 Cytochrome P450 2C9 1
20933411 10.1016/j.bmcl.2010.09.087 Phosphodiesterase 4 1
20933411 10.1016/j.bmcl.2010.09.087 3',5'-cyclic-AMP phosphodiesterase 4D 1
20933411 10.1016/j.bmcl.2010.09.087 3',5'-cyclic-AMP phosphodiesterase 4B 1

Data from ChEMBL 36 via Core Engine