deguelin

Deguelin is a derivative of rotenone. Both are compounds classified as rotenoids of the flavonoid family and are naturally occurring insecticides. They can be produced by extraction from several plant species belonging to three genera of the legume family, Fabaceae: Lonchocarpus, Derris, or Tephrosia.

Chemical data

Formula: C23H22O6
Molecular weight: 394.4 g/mol
IUPAC name: (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one
SMILES: CC1(C=CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC)C
InChIKey: ORDAZKGHSNRHTD-UXHICEINSA-N
XLogP: 3.7
Polar surface area: 63.2 Å²
H-bond donors: 0
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 394.142

Show 5 more facts

found in taxon: Derris
chemical formula: C₂₃H₂₂O₆
canonical SMILES: CC1(C=CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC)C
isomeric SMILES: CC1(C=CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC)C
Commons category: Deguelin

Sources (3)

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Encyclopedic overview

5 sections

Contents

Rat pharmacokinetics
Deguelin and anti-cancer activity
Deguelin and Parkinson's disease
References
External links

Cubé resin, the root extract from cubé (Lonchocarpus utilis) and from barbasco (Lonchocarpus urucu), is used as a commercial insecticide and piscicide (fish poison). The major active ingredients are rotenone and deguelin. Although "organic" (produced by nature) cubé resin is no longer considered environmentally safe.

Excerpted from Wikipedia’s “deguelin” article, available under the CC BY-SA 4.0 licence.