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Compound Detail

CHEMBL253083

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CC(C)(c1cc(-c2cccc(-c3ccc(C4CC4C(=O)O)cc3)c2)c2ncccc2c1)S(C)(=O)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL253083
Phase Preclinical
Structure Type MOL
InChI Key LWGNZANWYDVSLC-UHFFFAOYSA-N
8
Targets
17
Activities
1
Assay Types
5
PK Parameters
13
Publications
0
Known Names

Molecular Properties

485.6
MW (Da)
6.04
ALogP
4
HBA
1
HBD
84.3
PSA (Ų)
0.36
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H27NO4S
MW 485.61
Aromatic Rings 4
Heavy Atoms 35
NP-Likeness -0.33

Activity Summary

IC50 17 meas. best 9.49

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 9.49 9.38 0.3 2
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 9.49 9.38 0.3 2
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 9.49 9.38 0.3 2
Unchecked
CHEMBL612545
 IC50 9.1 8.975 0.8 2
Blood
CHEMBL613397
 IC50 7.47 7.47 34.0 1
Phosphodiesterase 4
CHEMBL2093863
 IC50 6.22 6.035 600.0 2
Blood
CHEMBL613416
 IC50 6.22 6.035 600.0 2
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.77 5.635 1700.0 4

Pharmacokinetic Data

Parameter Value Units Species
Cmax 65000.0 nM Saimiri sciureus
F 100.0 % Rattus norvegicus
F 100.0 % Rattus norvegicus
T1/2 2.0 hr Rattus norvegicus
T1/2 2.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.32 nM 9.49 Inhibition of PDE4B 20933411
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.32 nM 9.49 Inhibition of PDE4D 20933411
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 0.32 nM 9.49 Inhibition of PDE4A 20933411
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 0.54 nM 9.27 Inhibition of PDE4A 20933411
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.54 nM 9.27 Inhibition of PDE4B 20933411
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.54 nM 9.27 Inhibition of PDE4D 20933411
Unchecked IC50 = 0.8 nM 9.1 Inhibition of PDE4 expressed in SF9 cells 18207397
Unchecked IC50 = 1.4 nM 8.85 Inhibition of PDE4 expressed in SF9 cells 18207397
Blood IC50 = 34.0 nM 7.47 Inhibition of LPS-stimulated TNFalpha release in squirrel monkey whole blood 18207397
Blood IC50 = 600.0 nM 6.22 Inhibition of LPS-stimulated TNFalpha release in human whole blood 18207397
Phosphodiesterase 4 IC50 = 600.0 nM 6.22 Inhibition of PDE4 activity in human whole blood assessed as inhibition of LPS-i... 20933411
Blood IC50 = 1400.0 nM 5.85 Inhibition of LPS-stimulated TNFalpha release in human whole blood 18207397
Phosphodiesterase 4 IC50 = 1400.0 nM 5.85 Inhibition of PDE4 activity in human whole blood assessed as inhibition of LPS-i... 20933411
Cytochrome P450 2C9 IC50 = 1700.0 nM 5.77 Inhibition of CYP2C9 18207397
Cytochrome P450 2C9 IC50 = 1700.0 nM 5.77 Competitive inhibition of CYP2C9 20933411
Cytochrome P450 2C9 IC50 = 3200.0 nM 5.5 Inhibition of CYP2C9 18207397
Cytochrome P450 2C9 IC50 = 3200.0 nM 5.5 Competitive inhibition of CYP2C9 20933411

Literature References

PubMed DOI Target Context # Activities
18207397 10.1016/j.bmcl.2008.01.004 Rattus norvegicus 4
18207397 10.1016/j.bmcl.2008.01.004 Blood 3
18207397 10.1016/j.bmcl.2008.01.004 Unchecked 2
18207397 10.1016/j.bmcl.2008.01.004 Cytochrome P450 2C9 2
20933411 10.1016/j.bmcl.2010.09.087 3',5'-cyclic-AMP phosphodiesterase 4A 2
20933411 10.1016/j.bmcl.2010.09.087 3',5'-cyclic-AMP phosphodiesterase 4B 2
20933411 10.1016/j.bmcl.2010.09.087 3',5'-cyclic-AMP phosphodiesterase 4D 2
20933411 10.1016/j.bmcl.2010.09.087 Phosphodiesterase 4 2
20933411 10.1016/j.bmcl.2010.09.087 Cytochrome P450 2C9 2
20933411 10.1016/j.bmcl.2010.09.087 Unchecked 2
18207397 10.1016/j.bmcl.2008.01.004 Squirrel monkey 1
18207397 10.1016/j.bmcl.2008.01.004 Cavia porcellus 1
18207397 10.1016/j.bmcl.2008.01.004 ADMET 1

Data from ChEMBL 36 via Core Engine