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Compound Detail

CHEMBL77826

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O=C(O)c1ccc(-c2cc3cccnc3c(-c3ccc4nonc4c3)n2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL77826
Phase Preclinical
Structure Type MOL
InChI Key IALXIRPKVRUJQO-UHFFFAOYSA-N
7
Targets
22
Activities
2
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

368.4
MW (Da)
4.20
ALogP
6
HBA
1
HBD
102.0
PSA (Ų)
0.51
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 C21H12N4O3
MW 368.35
Aromatic Rings 5
Heavy Atoms 28
NP-Likeness -1.01

Activity Summary

IC50 20 meas. best 9.0
EC50 2 meas. best 7.17

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Phosphodiesterase 4
CHEMBL2093863
 IC50 9.0 8.085 1.0 2
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 8.82 8.82 1.5 6
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 7.47 7.47 34.0 4
Unchecked
CHEMBL612545
 EC50 7.17 7.17 67.6 1
PBMC
CHEMBL613107
 IC50 7.17 7.17 68.0 1
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 EC50 6.6 6.6 250.0 1
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 6.54 6.284 290.0 5
3',5'-cyclic-AMP phosphodiesterase 4C
CHEMBL291
 IC50 5.91 5.91 1230.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3210.91 ng.hr.mL-1 Rattus norvegicus
AUC 3211.28 ng.hr.mL-1 Rattus norvegicus
CL 2.34 mL.min-1.kg-1 Rattus norvegicus
CL 2.34 mL.min-1.kg-1 Rattus norvegicus
Cmax 2400.0 nM Rattus norvegicus
Cmax 2400.0 nM Rattus norvegicus
F 8.0 % Rattus norvegicus
F 8.0 % Rattus norvegicus
T1/2 12.0 hr Rattus norvegicus
T1/2 0.2 hr Rattus norvegicus
Tmax 3.5 hr Rattus norvegicus
Tmax 3.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Phosphodiesterase 4 IC50 = 1.0 nM 9.0 Inhibition of [3H]rolipram binding in human peripheral blood mononuclear cells 11755362
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1.5 nM 8.82 Inhibition of human Phosphodiesterase 4D from peripheral blood mononuclear cells 11755362
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1.5 nM 8.82 Inhibition of PDE4D 18686943
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1.5 nM 8.82 Inhibition of human PDE4D 22889281
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1.5 nM 8.82 Inhibition of human PDE4D 26288344
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1.5 nM 8.82 Inhibition of PDE4D (unknown origin) 35033884
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1.5 nM 8.82 Inhibition of human recombinant PDE4D 33569941
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 34.0 nM 7.47 Inhibition of human Phosphodiesterase 4B from peripheral blood mononuclear cells 11755362
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 34.0 nM 7.47 Inhibition of human PDE4B 22889281
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 34.0 nM 7.47 Inhibition of PDE4B (unknown origin) 26288344
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 34.0 nM 7.47 Inhibition of human recombinant PDE4B 33569941
Unchecked EC50 = 67.6 nM 7.17 Anti-inflammatory activity against human PBMCs assessed as reduction in LPS-indu... 33569941
PBMC IC50 = 68.0 nM 7.17 Inhibition of TNF-alpha release from human peripheral blood mononuclear cells 11755362
Phosphodiesterase 4 IC50 = 67.6 nM 7.17 Inhibition of PDE4 in human PBMC assessed as inhibition of LPS-induced TNFalpha ... 22889281
3',5'-cyclic-AMP phosphodiesterase 4A EC50 = 250.0 nM 6.6 Induction of SQSTM1-dependent intracellular redistribution of GFP-tagged PDE4A4 ... 21456625
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 290.0 nM 6.54 Inhibition of full-length PDE4A4 using cAMP as substrate by two-step radiochemic... 21456625
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 602.0 nM 6.22 Inhibition of human Phosphodiesterase 4A from peripheral blood mononuclear cells 11755362
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 602.0 nM 6.22 Inhibition of human PDE4A 22889281
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 602.0 nM 6.22 Inhibition of PDE4A (unknown origin) 26288344
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 602.0 nM 6.22 Inhibition of human recombinant PDE4A 33569941

Literature References

PubMed DOI Target Context # Activities
26288344 10.1021/acs.jmedchem.5b00902 Rattus norvegicus 7
22889281 10.1021/jm300459a Rattus norvegicus 7
22889281 10.1021/jm300459a No relevant target 2
21456625 10.1021/jm200070e 3',5'-cyclic-AMP phosphodiesterase 4A 2
18686943 10.1021/jm800582j 3',5'-cyclic-AMP phosphodiesterase 4D 1
33569941 10.1021/acs.jmedchem.0c01901 Rattus norvegicus 1
22889281 10.1021/jm300459a Phosphodiesterase 4 1
22889281 10.1021/jm300459a ADMET 1
22889281 10.1021/jm300459a 3',5'-cyclic-AMP phosphodiesterase 4A 1
22889281 10.1021/jm300459a 3',5'-cyclic-AMP phosphodiesterase 4B 1
22889281 10.1021/jm300459a 3',5'-cyclic-AMP phosphodiesterase 4D 1
11755362 10.1016/s0960-894x(01)00720-x 3',5'-cyclic-AMP phosphodiesterase 4A 1
11755362 10.1016/s0960-894x(01)00720-x PBMC 1
11755362 10.1016/s0960-894x(01)00720-x Phosphodiesterase 4 1
11755362 10.1016/s0960-894x(01)00720-x cGMP-specific 3',5'-cyclic phosphodiesterase 1
11755362 10.1016/s0960-894x(01)00720-x Phosphodiesterase 3 1
11755362 10.1016/s0960-894x(01)00720-x cGMP-dependent 3',5'-cyclic phosphodiesterase 1
11755362 10.1016/s0960-894x(01)00720-x Phosphodiesterase 1 1
11755362 10.1016/s0960-894x(01)00720-x 3',5'-cyclic-AMP phosphodiesterase 4D 1
11755362 10.1016/s0960-894x(01)00720-x 3',5'-cyclic-AMP phosphodiesterase 4C 1

Data from ChEMBL 36 via Core Engine