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Compound Detail

CHEMBL4745832

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COc1ccc2c3c([nH]c2c1)[C@@H]1N(CC3)C(=O)c2c(OC)cccc2N1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4745832
Phase Preclinical
Structure Type MOL
InChI Key WNMIZGXEPWFQCU-FQEVSTJZSA-N
9
Targets
9
Activities
1
Assay Types
11
PK Parameters
20
Publications
0
Known Names

Molecular Properties

363.4
MW (Da)
3.33
ALogP
4
HBA
1
HBD
57.8
PSA (Ų)
0.76
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H21N3O3
MW 363.42
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness 0.23

Activity Summary

IC50 9 meas. best 7.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 IC50 7.38 7.38 42.0 1
Unchecked
CHEMBL612545
 IC50 5.61 5.61 2482.0 1
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
CHEMBL4409
 IC50 5.52 5.52 3000.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.0 5.0 10000.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 5.0 5.0 10000.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.0 5.0 10000.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.0 5.0 10000.0 1
Cytochrome P450 2B6
CHEMBL4729
 IC50 5.0 5.0 10000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.7 4.7 20000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 519.0 ng.hr.mL-1 Rattus norvegicus
AUC 520.0 ng.hr.mL-1 Rattus norvegicus
AUC 146.0 ng.hr.mL-1 Rattus norvegicus
AUC 155.0 ng.hr.mL-1 Rattus norvegicus
Cmax 4944.69 nM Rattus norvegicus
Cmax 149.69 nM Rattus norvegicus
F 14.0 % Rattus norvegicus
T1/2 0.22 hr Rattus norvegicus
T1/2 1.43 hr Rattus norvegicus
Tmax 0.083 hr Rattus norvegicus
Tmax 0.83 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 42.0 nM 7.38 Inhibition of human PDE5A1 (535-860 residues) expressed in Escherichia coli BL21... 32794708
Unchecked IC50 = 2482.0 nM 5.61 Inhibition of human PDE5A1 D563A mutant expressed in Escherichia coli BL21 incub... 32794708
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 3000.0 nM 5.52 Inhibition of human PDE10A catalytic domain (449 to 770 residues) using [3H]-cAM... 32794708
Cytochrome P450 1A2 IC50 = 10000.0 nM 5.0 Inhibition of CYP1A2 (unknown origin) 32794708
Cytochrome P450 2B6 IC50 = 10000.0 nM 5.0 Inhibition of CYP2B6 (unknown origin) 32794708
Cytochrome P450 2C9 IC50 = 10000.0 nM 5.0 Inhibition of CYP2C9 (unknown origin) 32794708
Cytochrome P450 2D6 IC50 = 10000.0 nM 5.0 Inhibition of CYP2D6 (unknown origin) 32794708
Cytochrome P450 3A4 IC50 = 10000.0 nM 5.0 Inhibition of CYP3A4 (unknown origin) 32794708
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 20000.0 nM 4.7 Inhibition of human ERG expressed in CHO cells by patch-clamp electrophysiology ... 32794708

Literature References

PubMed DOI Target Context # Activities
32794708 10.1021/acs.jmedchem.0c00983 ADMET 15
32794708 10.1021/acs.jmedchem.0c00983 cGMP-specific 3',5'-cyclic phosphodiesterase 13
32794708 10.1021/acs.jmedchem.0c00983 Unchecked 12
32794708 10.1021/acs.jmedchem.0c00983 Rattus norvegicus 3
32794708 10.1021/acs.jmedchem.0c00983 High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A 1
32794708 10.1021/acs.jmedchem.0c00983 Voltage-gated inwardly rectifying potassium channel KCNH2 1
32794708 10.1021/acs.jmedchem.0c00983 Cytochrome P450 2D6 1
32794708 10.1021/acs.jmedchem.0c00983 Cytochrome P450 2C9 1
32794708 10.1021/acs.jmedchem.0c00983 Cytochrome P450 2B6 1
32794708 10.1021/acs.jmedchem.0c00983 Cytochrome P450 1A2 1
32794708 10.1021/acs.jmedchem.0c00983 Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A 1
32794708 10.1021/acs.jmedchem.0c00983 cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A 1
32794708 10.1021/acs.jmedchem.0c00983 High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A 1
32794708 10.1021/acs.jmedchem.0c00983 High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 1
32794708 10.1021/acs.jmedchem.0c00983 3',5'-cyclic-AMP phosphodiesterase 4D 1
32794708 10.1021/acs.jmedchem.0c00983 cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A 1
32794708 10.1021/acs.jmedchem.0c00983 cGMP-dependent 3',5'-cyclic phosphodiesterase 1
32794708 10.1021/acs.jmedchem.0c00983 Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B 1
32794708 10.1021/acs.jmedchem.0c00983 DNA topoisomerase 1 1
32794708 10.1021/acs.jmedchem.0c00983 DNA topoisomerase 2-alpha 1

Data from ChEMBL 36 via Core Engine