Structure Database (LMSD)
Common Name
Rotenone
Systematic Name
(2R,6aS,12aS)-1,2,6,6a,12,12a- hexahydro-2-isopropenyl-8,9- dimethoxychromeno[3,4-b] furo(2,3-h)chromen-6-one
Synonyms
- Tubotoxin
3D model of Rotenone
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Rotenone is a classical inhibitor of complex I of the mitochondrial electron transport chain, inhibiting NADH/DB oxidoreductase and NADH oxidase with IC50 values of 28.8 and 5.1 nM, respectively.1 In substantia nigra pars compacta neurons, it activates ATP-sensitive potassium channels and increases the production of reactive oxygen species (ROS) in the mitochondria, effects that are decreased by the antioxidant trolox .2 In rodents, rotenone induces dopaminergic cell death in the substantia nigra, formation of cytoplasmic inclusions similar to Lewy bodies, oxidative damage to proteins, and parkinsonian symptoms of bradykinesia and rigidity.3 In a rat model of Parkinson’s disease, chronic rotenone administration of 1.5 and 2.5 mg/kg per day for two months reduces tyrosine hydroxylase levels in the posterior striatum and prefrontal cortex, induces catalepsy, and decreases spontaneous locomotion and exploration in the open field test.4 Formulations containing rotenone have been used as insecticides and piscicides.5
This information has been provided by Cayman Chemical
References
1. Alam, M., and Schmidt, W.J. Rotenone destroys dopaminergic neurons and induces parkinsonian symptoms in rats. Behav. Brain Res. 136(1), 317-324 (2002).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
JUVIOZPCNVVQFO-HBGVWJBISA-N
InChi (Click to copy)
InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1
SMILES (Click to copy)
C12O[C@@]([H])(C(=C)C)CC1=C1O[C@]3([H])COC4C=C(OC)C(OC)=CC=4[C@]3([H])C(=O)C1=CC=2
Other Databases
KEGG ID
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
29
Rings
5
Aromatic Rings
2
Rotatable Bonds
3
Van der Waals Molecular Volume
354.48
Topological Polar Surface Area
69.43
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
6
logP
4.56
Molar Refractivity
107.42
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Updated at
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