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Compound Detail

CHEMBL4462192

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CCCOc1ccc(NC(=O)CN2CCN(C)CC2)cc1-c1nc(CC)c(CC)c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4462192
Phase Preclinical
Structure Type MOL
InChI Key PIOIVHHIGWTEJQ-UHFFFAOYSA-N
4
Targets
5
Activities
2
Assay Types
25
PK Parameters
20
Publications
0
Known Names

Molecular Properties

441.6
MW (Da)
2.54
ALogP
6
HBA
2
HBD
90.6
PSA (Ų)
0.62
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H35N5O3
MW 441.58
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness -1.55

Activity Summary

IC50 4 meas. best 9.21
Kd 1 meas. best 7.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 IC50 9.21 9.21 0.6 1
Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'
CHEMBL3977
 IC50 7.7 7.7 19.8 1
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 Kd 7.09 7.09 82.0 1
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A
CHEMBL2717
 IC50 6.0 6.0 998.0 1
Phosphodiesterase 1
CHEMBL2095150
 IC50 5.44 5.44 3640.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 403.0 ng.hr.mL-1 Rattus norvegicus
AUC 268.0 ng.hr.mL-1 Rattus norvegicus
AUC 412.0 ng.hr.mL-1 Rattus norvegicus
AUC 284.0 ng.hr.mL-1 Rattus norvegicus
AUC 752.0 ng.hr.mL-1 Canis lupus familiaris
AUC 495.0 ng.hr.mL-1 Canis lupus familiaris
AUC 773.0 ng.hr.mL-1 Canis lupus familiaris
AUC 514.0 ng.hr.mL-1 Canis lupus familiaris
CL 37.67 mL.min-1.kg-1 Rattus norvegicus
CL 10.8 mL.min-1.kg-1 Canis lupus familiaris
Cmax 99.42 nM Rattus norvegicus
Cmax 150.6 nM Canis lupus familiaris
F 66.4 % Rattus norvegicus
F 67.0 % Canis lupus familiaris
MRT 2.22 hr Rattus norvegicus
MRT 5.56 hr Rattus norvegicus
MRT 6.07 hr Canis lupus familiaris
MRT 7.21 hr Canis lupus familiaris
T1/2 2.4 hr Rattus norvegicus
T1/2 2.82 hr Rattus norvegicus
T1/2 4.5 hr Canis lupus familiaris
T1/2 4.89 hr Canis lupus familiaris
T1/2 10.9 hr Homo sapiens
Tmax 2.8 hr Rattus norvegicus
Tmax 1.9 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 0.62 nM 9.21 Inhibition of N-terminal GST-tagged human PDE5A1 expressed in baculovirus infect... 31021628
Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' IC50 = 19.8 nM 7.7 Inhibition of N-terminal GST-tagged human PDE6C expressed in baculovirus infecte... 31021628
cGMP-specific 3',5'-cyclic phosphodiesterase Kd = 82.0 nM 7.09 Binding affinity to recombinant human PDE5A1 catalytic domain (535 to 860 residu... 31021628
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A IC50 = 998.0 nM 6.0 Inhibition of N-terminal GST-tagged human PDE11A4 expressed in baculovirus infec... 31021628
Phosphodiesterase 1 IC50 = 3640.0 nM 5.44 Inhibition of N-terminal GST-tagged human PDE1 expressed in baculovirus infected... 31021628

Literature References

PubMed DOI Target Context # Activities
31021628 10.1021/acs.jmedchem.9b00123 ADMET 28
31021628 10.1021/acs.jmedchem.9b00123 Unchecked 10
31021628 10.1021/acs.jmedchem.9b00123 Rattus norvegicus 6
31021628 10.1021/acs.jmedchem.9b00123 cGMP-specific 3',5'-cyclic phosphodiesterase 5
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
- 10.6019/CHEMBL5724796 Tyrosine-protein kinase ABL1 1
- 10.6019/CHEMBL5724796 Aurora kinase A 1
- 10.6019/CHEMBL5724796 Mitogen-activated protein kinase 1 1
- 10.6019/CHEMBL5724796 Glycogen synthase kinase-3 beta 1
- 10.6019/CHEMBL5724796 Cyclin-dependent kinase 2 1
- 10.6019/CHEMBL5724796 Casein kinase I isoform delta 1
31021628 10.1021/acs.jmedchem.9b00123 Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A 1
31021628 10.1021/acs.jmedchem.9b00123 cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A 1
31021628 10.1021/acs.jmedchem.9b00123 High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A 1
31021628 10.1021/acs.jmedchem.9b00123 High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A 1
31021628 10.1021/acs.jmedchem.9b00123 Phosphodiesterase 7 1
31021628 10.1021/acs.jmedchem.9b00123 Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' 1
31021628 10.1021/acs.jmedchem.9b00123 Phosphodiesterase 4 1
31021628 10.1021/acs.jmedchem.9b00123 Phosphodiesterase 3 1
31021628 10.1021/acs.jmedchem.9b00123 cGMP-dependent 3',5'-cyclic phosphodiesterase 1

Data from ChEMBL 36 via Core Engine