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Compound Detail

CHEMBL484928

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Cc1ccc([N+](=O)[O-])cc1S(=O)(=O)N(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL484928
Phase Preclinical
Structure Type MOL
InChI Key IFIUFCJFLGCQPH-UHFFFAOYSA-N
10
Targets
23
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

244.3
MW (Da)
1.15
ALogP
4
HBA
0
HBD
80.5
PSA (Ų)
0.59
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 C9H12N2O4S
MW 244.27
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness -2.35

Activity Summary

IC50 23 meas. best 7.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A
CHEMBL3012
 IC50 7.05 6.378 90.0 10
3',5'-cyclic-AMP phosphodiesterase 7B
CHEMBL4716
 IC50 6.21 5.565 620.0 2
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 5.89 5.89 1280.0 1
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 5.75 5.75 1800.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.0 4.95 10000.0 2
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 IC50 4.21 4.21 62000.0 1
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 4.21 4.21 62000.0 1
cGMP-dependent 3',5'-cyclic phosphodiesterase
CHEMBL2652
 IC50 4.21 4.21 62000.0 1
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B
CHEMBL4425
 IC50 4.21 4.21 62000.0 1
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C
CHEMBL4619
 IC50 4.21 4.21 62000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A IC50 = 90.0 nM 7.05 Inhibition of human recombinant PDE7A1 assessed as inhibition of hydrolysis of [... 25264825
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A IC50 = 90.0 nM 7.05 Displacement of [3H]-cAMP from recombinant human PDE7A1 incubated for 20 mins by... 35144038
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A IC50 = 90.0 nM 7.05 Inhibition of human recombinant PDE7A1-mediated [3H]cAMP hydrolysis after 20 min... 22385507
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A IC50 = 150.0 nM 6.82 Inhibition of PDE7A (unknown origin) 38614063
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A IC50 = 260.0 nM 6.58 Inhibition of human PDE7A1 34042442
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A IC50 = 260.0 nM 6.58 Inhibition of recombinant PDE7A1 (130 to 482 residues) (unknown origin) expresse... 36796299
3',5'-cyclic-AMP phosphodiesterase 7B IC50 = 620.0 nM 6.21 Inhibition of PDE7B (unknown origin) by 3H-cAMP scintillation proximity assay 36796299
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 1280.0 nM 5.89 Inhibition of human recombinant PDE4D3 assessed after 60 mins by IMAP fluorescen... 25264825
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 1800.0 nM 5.75 Inhibition of human recombinant PDE4B2 assessed after 60 mins by IMAP fluorescen... 25264825
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A IC50 = 2100.0 nM 5.68 Inhibition of recombinant human PDE7A using cAMP as substrate after 10 mins by P... 30245393
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A IC50 = 2100.0 nM 5.68 Inhibition of human GST-tagged PDE7A expressed in baculovirus infected Sf9 insec... 29407965
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A IC50 = 2200.0 nM 5.66 Inhibition of human recombinant PDE7A1 expressed in baculovirus-infected insect ... 19303290
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A IC50 = 2320.0 nM 5.63 Inhibition of human recombinant PDE7A using cAMP as substrate incubated for 20 m... 33022582
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
3',5'-cyclic-AMP phosphodiesterase 7B IC50 = 12100.0 nM 4.92 Inhibition of PDE7B (unknown origin) 38614063
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B IC50 = 62000.0 nM 4.21 Inhibition of human PDE1B 34042442
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C IC50 = 62000.0 nM 4.21 Inhibition of human PDE1C 34042442
cGMP-dependent 3',5'-cyclic phosphodiesterase IC50 = 62000.0 nM 4.21 Inhibition of human PDE2 34042442
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 62000.0 nM 4.21 Inhibition of human PDE5 34042442

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
31035240 10.1016/j.ejmech.2019.04.020 High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 3
19734910 10.1038/nchembio.215 Plasmodium falciparum 2
22385507 10.1021/jm201720d High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 2
22385507 10.1021/jm201720d NON-PROTEIN TARGET 2
25264825 10.1021/jm501090m High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
19303290 10.1016/j.bmcl.2009.03.007 High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 1
34042442 10.1021/acs.jmedchem.1c00115 High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 1
35144038 10.1016/j.ejmech.2022.114170 High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 1
33022582 10.1016/j.ejmech.2020.112854 High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
30245393 10.1016/j.ejmech.2018.09.021 3',5'-cyclic-AMP phosphodiesterase 4B 1
30245393 10.1016/j.ejmech.2018.09.021 High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 1
29407965 10.1016/j.ejmech.2018.01.068 High affinity 3',5'-cyclic-AMP phosphodiesterase 7A 1
29407965 10.1016/j.ejmech.2018.01.068 3',5'-cyclic-AMP phosphodiesterase 4B 1
25264825 10.1021/jm501090m 3',5'-cyclic-AMP phosphodiesterase 4B 1
25264825 10.1021/jm501090m 3',5'-cyclic-AMP phosphodiesterase 4D 1

Data from ChEMBL 36 via Core Engine