EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:28201 - rotenone

Default Structure
ChEBI IDCHEBI:28201
ChEBI Namerotenone
Stars
DefinitionA member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica).
Secondary ChEBI IDsCHEBI:8897, CHEBI:26583
Last Modified28 May 2021
DownloadsMolfile
FormulaC23H22O6
Net Charge0
Average Mass394.423
Monoisotopic Mass394.14164
SMILES[H][C@]1(C(=C)C)Cc2c(ccc3c2O[C@]2([H])COc4cc(OC)c(OC)cc4[C@]2([H])C3=O)O1
InChIInChI=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
InChIKeyJUVIOZPCNVVQFO-HBGVWJBISA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Antheroporum pierrei (IPNI:474590-1)
twig (BTO:0001411) PubMed (21452840) Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1)
leaf (BTO:0000713) PubMed (21452840) Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1)
Derris elliptica (ncbitaxon:56063) - DOI (10.1016/S0040-4020(01)93394-0)
Erycibe expansa (IPNI:267866-1) stem (BTO:0001300) PubMed (17077549)
Mundulea chapelieri (IPNI:20004737-1)
bark (BTO:0001301) PubMed (15043430)
leaf (BTO:0000713) PubMed (15043430)
flower (BTO:0000469) PubMed (15043430)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
piscicide  A substance which is poisonous to fish and is primarily used to eliminate dominant species of fish in water.
phytogenic insecticide  An insecticide compound naturally occurring in plants.
ChEBI Ontology
Outgoing Relation(s)
rotenone (CHEBI:28201) has role antineoplastic agent (CHEBI:35610)
rotenone (CHEBI:28201) has role metabolite (CHEBI:25212)
rotenone (CHEBI:28201) has role mitochondrial NADH:ubiquinone reductase inhibitor (CHEBI:38498)
rotenone (CHEBI:28201) has role phytogenic insecticide (CHEBI:22917)
rotenone (CHEBI:28201) has role piscicide (CHEBI:167183)
rotenone (CHEBI:28201) has role toxin (CHEBI:27026)
rotenone (CHEBI:28201) is a organic heteropentacyclic compound (CHEBI:38164)
rotenone (CHEBI:28201) is a rotenones (CHEBI:72581)
IUPAC Name 
(2R,6aS,12aS)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
Synonyms  Source
(12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano[3,4-b]furano [2,3-h]chroman-6-oneChEBI
[2R-(2α,6aα,12aα)]-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6aH)-oneNIST Chemistry WebBook
5'β-rotenoneNIST Chemistry WebBook
barbascoChemIDplus
canexChemIDplus
dactinolChemIDplus
Manual XrefsDatabases
587VSDB
587BPDB
970PDBeChem
C00002568KNApSAcK
C07593KEGG COMPOUND
CN102007944Patent
CN102090406Patent
DB11457DrugBank
FDB012837FooDB
HMDB0034436HMDB
LMPK12060007LIPID MAPS
LSM-5260LINCS
RotenoneWikipedia
Registry NumbersSources
Reaxys:99070Reaxys
CAS:83-79-4ChemIDplus
CAS:83-79-4KEGG COMPOUND
CAS:83-79-4NIST Chemistry WebBook
Citations