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
LM ID
LMPK12060007
Formula
Exact Mass
Calculate m/z
394.14164
Status
Curated




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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