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Compound Detail

CHEMBL397686

DIPHENYLENEIODONIUM CHLORIDE
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[Cl-].c1ccc2c(c1)[I+]c1ccccc1-2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL397686
Name DIPHENYLENEIODONIUM CHLORIDE
Phase Preclinical
Structure Type MOL
InChI Key FCFZKAVCDNTYID-UHFFFAOYSA-M
Parent Compound CHEMBL365739
Active Moiety CHEMBL365739
8
Targets
28
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

279.1
MW (Da)
-0.20
ALogP
0
HBA
0
HBD
0.0
PSA (Ų)
0.50
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C12H8ClI
MW 314.55
Aromatic Rings 2
Heavy Atoms 13
NP-Likeness -0.10

Activity Summary

IC50 26 meas. best 10.22
EC50 2 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 10.22 8.1081 0.1 16
NADPH oxidase 5
CHEMBL1926497
 IC50 7.7 7.7 20.0 1
NADPH oxidase 4
CHEMBL1250375
 IC50 7.05 7.05 90.0 1
Cytochrome b-245 heavy chain
CHEMBL1287627
 IC50 7.0 7.0 100.0 1
NADPH oxidase 1
CHEMBL1287628
 IC50 6.62 6.62 240.0 1
G-protein coupled receptor 3
CHEMBL4523856
 EC50 6.0 5.645 1000.0 2
Neutrophil
CHEMBL613710
 IC50 5.75 5.464 1800.0 5
Rattus norvegicus
CHEMBL376
 IC50 5.37 5.37 4300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.06 nM 10.22 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.06 nM 10.22 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.07 nM 10.15 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.08 nM 10.1 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 0.09 nM 10.05 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.1 nM 10.0 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1.0 nM 9.0 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
NADPH oxidase 5 IC50 = 20.0 nM 7.7 Inhibition of human NOX5 expressed in HEK293 cells assessed as inhibition of ion... 37650225
Plasmodium falciparum IC50 = 50.12 nM 7.3 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 63.1 nM 7.2 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 63.1 nM 7.2 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 79.43 nM 7.1 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 79.43 nM 7.1 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
NADPH oxidase 4 IC50 = 90.0 nM 7.05 Inhibition of human NOX4 expressed in HEK293T cells assessed as inhibition of te... 37650225
Plasmodium falciparum IC50 = 100.0 nM 7.0 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Cytochrome b-245 heavy chain IC50 = 100.0 nM 7.0 Inhibition of NOX2 in human PLB-985 cells assessed as inhibition of PMA-induced ... 37650225
NADPH oxidase 1 IC50 = 240.0 nM 6.62 Inhibition of human NOX1 expressed in CHO cells assessed as inhibition of PMA-in... 37650225
Plasmodium falciparum IC50 = 1000.0 nM 6.0 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
G-protein coupled receptor 3 EC50 = 1000.0 nM 6.0 Agonist activity at FLAG/GFP-tagged GPR3 (unknown origin)-mediated cAMP signalin... 37907069
Neutrophil IC50 = 1800.0 nM 5.75 Inhibition of PMA-stimulated super oxide anion generation in Sprague-Dawley rat ... 19278854

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 14
19278854 10.1016/j.bmc.2009.02.025 Neutrophil 4
37541631 10.1016/j.bmcl.2023.129427 G-protein coupled receptor 3 3
17320246 10.1016/j.ejmech.2006.12.009 Neutrophil 2
19097788 10.1016/j.bmcl.2008.11.071 Plasmodium falciparum 2
37541631 10.1016/j.bmcl.2023.129427 G-protein coupled receptor 6 2
37907069 10.1021/acs.jmedchem.3c01707 G-protein coupled receptor 3 1
37650225 10.1021/acs.jmedchem.3c00770 NADPH oxidase 4 1
37650225 10.1021/acs.jmedchem.3c00770 Cytochrome b-245 heavy chain 1
37650225 10.1021/acs.jmedchem.3c00770 NADPH oxidase 1 1
37541631 10.1016/j.bmcl.2023.129427 Unchecked 1
37541631 10.1016/j.bmcl.2023.129427 G-protein coupled receptor 12 1
- 10.6019/EOS300108 HepG2 1
28384544 10.1016/j.ejmech.2017.03.049 RAW264.7 1
24466406 10.1039/c3md00061c Xanthine dehydrogenase/oxidase 1
17417631 10.1038/nchembio873 Unchecked 1
19699097 10.1016/j.bmc.2009.07.054 Rattus norvegicus 1
19699097 10.1016/j.bmc.2009.07.054 Neutrophil 1
19097788 10.1016/j.bmcl.2008.11.071 Dihydroorotate dehydrogenase (fumarate) 1
19097788 10.1016/j.bmcl.2008.11.071 Dihydroorotate dehydrogenase 1

Data from ChEMBL 36 via Core Engine