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Compound Detail

CHEMBL429023

ROTENONE
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C=C(C)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(OC)c(OC)cc4[C@@H]2C3=O)O1

Basic Information

ChEMBL ID CHEMBL429023
Name ROTENONE
Phase Preclinical
Structure Type MOL
InChI Key JUVIOZPCNVVQFO-HBGVWJBISA-N
20
Targets
54
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

394.4
MW (Da)
3.70
ALogP
6
HBA
0
HBD
63.2
PSA (Ų)
0.74
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C23H22O6
MW 394.42
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness 1.84

Activity Summary

IC50 49 meas. best 9.77
EC50 4 meas. best 6.3
Ki 1 meas. best 6.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome b-245 light chain
CHEMBL2366457
IC50 9.77 9.77 0.2 1
Unchecked
CHEMBL612545
IC50 8.7 7.0862 2.0 21
NADH-ubiquinone oxidoreductase chain 4
CHEMBL4499
IC50 8.46 8.46 3.5 1
NADH-ubiquinone oxidoreductase chain 1
CHEMBL4497
IC50 8.36 7.975 4.4 2
Mitochondrial complex I; NADH oxidoreductase
CHEMBL614865
IC50 8.29 8.29 5.1 1
L929
CHEMBL612267
IC50 7.79 7.79 16.1 1
U-937
CHEMBL612794
IC50 7.16 6.25 70.0 3
HT-29
CHEMBL384
IC50 6.52 6.52 300.0 1
L5178Y
CHEMBL614720
IC50 6.52 6.52 300.0 1
697
CHEMBL2366253
IC50 6.52 6.52 300.0 2
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 6.39 6.39 404.0 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 6.3 6.3 500.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 6.16 5.145 700.0 2
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 6.06 6.06 870.0 1
Raji
CHEMBL614628
IC50 5.96 5.67 1100.0 2
HepG2
CHEMBL395
IC50 5.82 5.82 1520.0 1
Caenorhabditis elegans
CHEMBL613135
EC50 5.7 5.7 2000.0 2
Cytochrome P450 2C19
CHEMBL3622
IC50 5.44 5.44 3648.6 1
Bile salt export pump
CHEMBL6020
IC50 5.1 5.1 8000.0 1
Drosophila
CHEMBL612724
EC50 5.0 5.0 10000.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.0 4.9667 10000.0 6
HeLa
CHEMBL399
IC50 4.11 4.11 78000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome b-245 light chain IC50 = 0.17 nM 9.77 Inhibition of Bos taurus (bovine) heart mitochondrial NADPH oxidase activity ass... -
Unchecked IC50 = 1.995 nM 8.7 Tested for the ability to block NADH dehydrogenase in a preparation of submitoch... -
NADH-ubiquinone oxidoreductase chain 4 IC50 = 3.5 nM 8.46 The compound was evaluated for the inhibition of NADH dehydrogenase -
Unchecked IC50 = 4.36 nM 8.36 Inhibition of NADH oxidase from beef heart submitochondrial particles by spectro... 20456960
NADH-ubiquinone oxidoreductase chain 1 IC50 = 4.4 nM 8.36 Inhibition of Bos taurus (beef) heart NAD1 16218678
Mitochondrial complex I; NADH oxidoreductase IC50 = 5.1 nM 8.29 Inhibitory activity against NADH oxidase in beef heart mitochondrial complex I. 14592516
Unchecked IC50 = 5.1 nM 8.29 Inhibition of NADH-ubiquinone oxidoreductase assessed by NADH oxidase activity i... 17482824
Unchecked IC50 = 5.1 nM 8.29 Inhibition of NADH oxidase in beef heart submitochondrial particles by end-windo... 19719247
Unchecked IC50 = 5.1 nM 8.29 Inhibition of NADH oxidase in beef heart sub-mitochondrial particles by UV-spect... 24012711
Unchecked IC50 = 6.9 nM 8.16 Inhibition of complex 1 in bovine heart mitochondrial membranes in presence of N... 32459967
Unchecked IC50 = 16.0 nM 7.8 Inhibition of mitochondrial complex 1 in bovine heart mitochondria assessed as e... 18422306
Unchecked IC50 = 16.0 nM 7.8 Inhibition of bovine mitochondrial MC1 17696417
L929 IC50 = 16.1 nM 7.79 Antiproliferative activity against mouse L929 cells assessed as inhibition of ce... 36893622
Unchecked IC50 = 19.3 nM 7.71 Inhibition of mitochondrial respiration in Sprague-Dawley rat liver 36893622
NADH-ubiquinone oxidoreductase chain 1 IC50 = 25.7 nM 7.59 Inhibition of Bos taurus (bovine) heart submitochondrial particle NDH1 assessed ... 8573592
Unchecked IC50 = 25.7 nM 7.59 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Unchecked IC50 = 28.8 nM 7.54 Inhibitory activity against NADH/DH oxidoreductase in beef heart mitochondrial c... 14592516
U-937 IC50 = 70.0 nM 7.16 Antiproliferative activity against human U937 cells after 72 hrs by WST-8 assay 17158054
Unchecked IC50 = 100.0 nM 7.0 Inhibition of mitochondrial complex1 (unknown origin) 33103432
Unchecked IC50 = 153.2 nM 6.82 PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmator... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1282
17158054 10.1016/j.bmc.2006.09.024 HT-1080 30
- 10.1584/jpestics.G10-52 Brontispa longissima 14
17726098 10.1073/pnas.0704482104 Unchecked 12
21875114 10.1021/np200370z Serine/threonine-protein kinase mTOR 10
17726098 10.1073/pnas.0704482104 NON-PROTEIN TARGET 7
20409720 10.1016/j.bmc.2010.03.075 Unchecked 6
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
22970736 10.1021/jf3032217 Callosobruchus maculatus 6
21875114 10.1021/np200370z T47D 5
6106061 10.1021/jm00183a011 Cavia porcellus 5
23245650 10.1021/np300711e MDA-MB-231 5
21370392 10.1002/ps.2125 Diaprepes abbreviatus 5
23434131 10.1016/j.bmc.2013.01.048 Unchecked 5
10869199 10.1021/np990328+ Myzus persicae 5
8573592 10.1016/0005-2728(95)00131-x Unchecked 4
15998112 10.1021/jf050110v Drosophila melanogaster 4
21875114 10.1021/np200370z MDA-MB-231 3
17158054 10.1016/j.bmc.2006.09.024 U-937 3
10869199 10.1021/np990328+ Spodoptera littoralis 3

Data from ChEMBL 36 via Core Engine