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Compound Detail

CHEMBL4099219

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O=c1c2ccccc2oc2c(Cc3ccc4c(c3)OCO4)[nH]c(-c3nccs3)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4099219
Phase Preclinical
Structure Type MOL
InChI Key ZUGQSSCMJHOUMY-UHFFFAOYSA-N
7
Targets
7
Activities
1
Assay Types
18
PK Parameters
20
Publications
0
Known Names

Molecular Properties

402.4
MW (Da)
4.72
ALogP
6
HBA
1
HBD
77.3
PSA (Ų)
0.47
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 C22H14N2O4S
MW 402.43
Aromatic Rings 5
Heavy Atoms 29
NP-Likeness -0.27

Activity Summary

IC50 7 meas. best 8.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 IC50 8.25 8.25 5.6 1
Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha
CHEMBL3878
 IC50 7.24 7.24 58.0 1
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
CHEMBL4409
 IC50 6.82 6.82 153.0 1
cGMP-dependent 3',5'-cyclic phosphodiesterase
CHEMBL2652
 IC50 6.44 6.44 362.0 1
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 5.56 5.56 2769.0 1
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A
CHEMBL4640
 IC50 5.21 5.21 6223.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 5.12 5.12 7600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1732.0 ng.hr.mL-1 Rattus norvegicus
AUC 2031.0 ng.hr.mL-1 Rattus norvegicus
AUC 1703.0 ng.hr.mL-1 Rattus norvegicus
AUC 1997.0 ng.hr.mL-1 Rattus norvegicus
CL 10.89 mL.min-1.kg-1 Homo sapiens
CL 35.61 mL.min-1.kg-1 Rattus norvegicus
CL 23.89 mL.min-1.kg-1 Homo sapiens
CL 101.0 mL.min-1.kg-1 Rattus norvegicus
CL 24.8 mL.min-1.g-1 Homo sapiens
CL 56.1 mL.min-1.g-1 Rattus norvegicus
Cmax 5861.89 nM Rattus norvegicus
Cmax 914.44 nM Rattus norvegicus
F 63.4 % Rattus norvegicus
T1/2 6.02 hr Rattus norvegicus
T1/2 5.17 hr Rattus norvegicus
T1/2 0.9333 hr Homo sapiens
T1/2 0.4117 hr Rattus norvegicus
Tmax 4.0 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 = 5.6 nM 8.25 Inhibition of PDE5A1 catalytic domain (535 to 860 residues) (unknown origin) exp... 28686445
Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha IC50 = 58.0 nM 7.24 Inhibition of PDE6A (484 to 817 residues) (unknown origin) expressed in Escheric... 28686445
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A IC50 = 153.0 nM 6.82 Inhibition of PDE10A (449 to 770 residues) (unknown origin) expressed in Escheri... 28686445
cGMP-dependent 3',5'-cyclic phosphodiesterase IC50 = 362.0 nM 6.44 Inhibition of PDE2A (580 to 919 residues) (unknown origin) expressed in Escheric... 28686445
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 2769.0 nM 5.56 Inhibition of PDE4D2 (86 to 413 residues) (unknown origin) expressed in Escheric... 28686445
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A IC50 = 6223.0 nM 5.21 Inhibition of PDE8A1 (480 to 820 residues) (unknown origin) using [3H]cGMP or [3... 28686445
Cytochrome P450 1A2 IC50 = 7600.0 nM 5.12 Inhibition of CYP1A2 in human microsomes in presence of NADPH 28686445

Literature References

PubMed DOI Target Context # Activities
28686445 10.1021/acs.jmedchem.7b00523 Rattus norvegicus 17
28686445 10.1021/acs.jmedchem.7b00523 Liver 12
28686445 10.1021/acs.jmedchem.7b00523 Unchecked 9
28686445 10.1021/acs.jmedchem.7b00523 Mus musculus 6
28686445 10.1021/acs.jmedchem.7b00523 Cytochrome P450 1A2 1
28686445 10.1021/acs.jmedchem.7b00523 Cytochrome P450 2C8 1
28686445 10.1021/acs.jmedchem.7b00523 Cytochrome P450 2C9 1
28686445 10.1021/acs.jmedchem.7b00523 Cytochrome P450 2C19 1
28686445 10.1021/acs.jmedchem.7b00523 Cytochrome P450 2D6 1
28686445 10.1021/acs.jmedchem.7b00523 Cytochrome P450 3A4 1
28686445 10.1021/acs.jmedchem.7b00523 Voltage-gated inwardly rectifying potassium channel KCNH2 1
28686445 10.1021/acs.jmedchem.7b00523 cGMP-specific 3',5'-cyclic phosphodiesterase 1
28686445 10.1021/acs.jmedchem.7b00523 Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B 1
28686445 10.1021/acs.jmedchem.7b00523 cGMP-dependent 3',5'-cyclic phosphodiesterase 1
28686445 10.1021/acs.jmedchem.7b00523 cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A 1
28686445 10.1021/acs.jmedchem.7b00523 3',5'-cyclic-AMP phosphodiesterase 4D 1
28686445 10.1021/acs.jmedchem.7b00523 Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha 1
28686445 10.1021/acs.jmedchem.7b00523 High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 1
28686445 10.1021/acs.jmedchem.7b00523 High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A 1
28686445 10.1021/acs.jmedchem.7b00523 High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A 1

Data from ChEMBL 36 via Core Engine