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Compound Detail

CHEMBL372575

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Cc1noc(/C(=C/c2cccc(-c3cc(C(C)(C)S(C)(=O)=O)cc4cccnc34)c2)c2ccc(S(C)(=O)=O)cc2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL372575
Phase Preclinical
Structure Type MOL
InChI Key YYGZHVJDHMMABU-OGLMXYFKSA-N
12
Targets
33
Activities
2
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

587.7
MW (Da)
5.87
ALogP
8
HBA
0
HBD
120.1
PSA (Ų)
0.22
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C31H29N3O5S2
MW 587.72
Aromatic Rings 5
Heavy Atoms 41
NP-Likeness -0.93

Activity Summary

IC50 32 meas. best 9.8
EC50 1 meas. best 4.97

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Phosphodiesterase 4
CHEMBL2093863
 IC50 9.8 8.92 0.2 3
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 9.3 9.2 0.5 3
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 9.0 8.8875 1.0 4
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 9.0 8.9467 1.0 3
Unchecked
CHEMBL612545
 IC50 8.52 7.03 3.0 5
3',5'-cyclic-AMP phosphodiesterase 4C
CHEMBL291
 IC50 8.04 8.04 9.1 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.0 8.0 10.0 1
Blood
CHEMBL613397
 IC50 7.96 7.96 11.0 2
Blood
CHEMBL613416
 IC50 6.8 6.775 160.0 4
Cytochrome P450 2C9
CHEMBL3397
 IC50 6.7 6.7 200.0 3
Trypanosoma brucei brucei
CHEMBL612851
 EC50 4.97 4.97 10800.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.3 4.3 49900.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 7.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 5100.0 nM Rattus norvegicus
Cmax 3800.0 nM Saimiri sciureus
Cmax 3000.0 nM Saimiri sciureus
Cmax 3800.0 nM Saimiri
F 100.0 % Rattus norvegicus
F 95.0 % Rattus norvegicus
F 55.0 % Canis lupus familiaris
F 33.0 % Saimiri sciureus
F 100.0 % Rattus norvegicus
T1/2 4.0 hr Rattus norvegicus
T1/2 5.0 hr Canis lupus familiaris
T1/2 4.0 hr Saimiri sciureus
Tmax 6.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Phosphodiesterase 4 IC50 = 0.16 nM 9.8 Inhibition of LPS-induced TNFalpha production in human whole blood 16168647
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.5 nM 9.3 Inhibitory activity against PDE4B 16168647
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.5 nM 9.3 Inhibition of human PDE4B 20709547
Phosphodiesterase 4 IC50 = 1.0 nM 9.0 Inhibition of human PDE4 19640717
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 1.0 nM 9.0 Inhibition of PDE4A 20933411
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 1.0 nM 9.0 Inhibition of PDE4B 20933411
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1.0 nM 9.0 Inhibition of PDE4D 20933411
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1.2 nM 8.92 Inhibitory activity against PDE4D 16168647
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1.2 nM 8.92 Inhibition of human PDE4D 20709547
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 1.4 nM 8.85 Inhibitory activity against PDE4A 16168647
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 1.4 nM 8.85 Intrinsic inhibition of GST-fused human PDE4A expressed in SF9 cells 18835163
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 1.4 nM 8.85 Inhibition of human PDE4A 20709547
Unchecked IC50 = 3.0 nM 8.52 Inhibition of PDE4 expressed in SF9 cells 18207397
Unchecked IC50 = 3.0 nM 8.52 Inhibition of PDE4 18686943
3',5'-cyclic-AMP phosphodiesterase 4C IC50 = 9.1 nM 8.04 Inhibition of human PDE4C 20709547
3',5'-cyclic-AMP phosphodiesterase 4C IC50 = 9.1 nM 8.04 Inhibitory activity against PDE4C 16168647
NON-PROTEIN TARGET IC50 = 10.0 nM 8.0 Antiinflammatory activity in squirrel monkey whole blood assessed as inhibition ... 19640717
Phosphodiesterase 4 IC50 = 11.0 nM 7.96 Inhibition of LPS-induced TNFalpha production in squirrel monkey whole blood 16168647
Blood IC50 = 11.0 nM 7.96 Inhibition of LPS-stimulated TNFalpha release in squirrel monkey whole blood 18207397
Blood IC50 = 11.0 nM 7.96 Inhibition of LPS-induced TNFalpha production in Squirrel monkey whole blood 18835163

Literature References

PubMed DOI Target Context # Activities
18835163 10.1016/j.bmcl.2008.09.009 Squirrel monkey 3
16168647 10.1016/j.bmcl.2005.08.036 Phosphodiesterase 4 3
20933411 10.1016/j.bmcl.2010.09.087 Nucleic Acid 3
22023548 10.1021/jm201148s Unchecked 3
16168647 10.1016/j.bmcl.2005.08.036 Rattus norvegicus 3
20933411 10.1016/j.bmcl.2010.09.087 Rattus norvegicus 3
19640717 10.1016/j.bmcl.2009.03.105 Rattus norvegicus 2
20933411 10.1016/j.bmcl.2010.09.087 Unchecked 2
20933411 10.1016/j.bmcl.2010.09.087 Plasma 2
20933411 10.1016/j.bmcl.2010.09.087 Brain 2
18835163 10.1016/j.bmcl.2008.09.009 Canis familiaris 2
18207397 10.1016/j.bmcl.2008.01.004 Blood 2
16168647 10.1016/j.bmcl.2005.08.036 Ovis aries 2
18835163 10.1016/j.bmcl.2008.09.009 Blood 2
19640717 10.1016/j.bmcl.2009.03.105 Saimiri 2
18835163 10.1016/j.bmcl.2008.09.009 Rattus norvegicus 2
22023548 10.1021/jm201148s Trypanosoma brucei brucei 1
18207397 10.1016/j.bmcl.2008.01.004 Squirrel monkey 1
18207397 10.1016/j.bmcl.2008.01.004 Unchecked 1
16168647 10.1016/j.bmcl.2005.08.036 3',5'-cyclic-AMP phosphodiesterase 4D 1

Data from ChEMBL 36 via Core Engine