CHEBI:28201 - rotenone

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ChEBI Name rotenone
ChEBI ID CHEBI:28201
Definition A 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).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:8897, CHEBI:26583
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Formula C23H22O6
Net Charge 0
Average Mass 394.41720
Monoisotopic Mass 394.142
InChI 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
InChIKey JUVIOZPCNVVQFO-HBGVWJBISA-N
SMILES [H][C@@]1(Cc2c(O1)ccc1C(=O)[C@@]3([H])c4cc(OC)c(OC)cc4OC[C@@]3([H])Oc21)C(C)=C
Metabolite of Species Details
Mundulea chapelieri (IPNI:20004737-1) Found in flower (BTO:0000469). See: PubMed
Mundulea chapelieri (IPNI:20004737-1) Found in leaf (BTO:0000713). See: PubMed
Mundulea chapelieri (IPNI:20004737-1) Found in bark (BTO:0001301). See: PubMed
Erycibe expansa (IPNI:267866-1) Found in stem (BTO:0001300). See: PubMed
Antheroporum pierrei (IPNI:474590-1) Found in twig (BTO:0001411). Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1) See: PubMed
Antheroporum pierrei (IPNI:474590-1) Found in leaf (BTO:0000713). Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1) See: PubMed
Derris elliptica (NCBI:56063) See: DOI
Roles Classification
Biological Role(s): toxin
Poisonous substance produced by a biological organism such as a microbe, animal or plant.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
mitochondrial NADH:ubiquinone reductase inhibitor

Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
phytogenic insecticide
An insecticide compound naturally occurring in plants.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
(−)-cis-rotenone ChemIDplus
(−)-rotenone ChemIDplus
(12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano[3,4-b]furano [2,3-h]chroman-6-one ChEBI
5'β-rotenone NIST Chemistry WebBook
[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)-one NIST Chemistry WebBook
barbasco ChemIDplus
canex ChemIDplus
dactinol ChemIDplus
Derris ChEBI
noxfire ChemIDplus
paraderil ChemIDplus
Rotenone KEGG COMPOUND
tubatoxin ChemIDplus
Database Links Databases
C00002568 KNApSAcK
C07593 KEGG COMPOUND
CN102007944 Patent
CN102090406 Patent
LMPK12060007 LIPID MAPS
LSM-5260 LINCS
Rotenone Wikipedia
View more database links
Registry Numbers Types Sources
83-79-4 CAS Registry Number ChemIDplus
83-79-4 CAS Registry Number NIST Chemistry WebBook
99070 Beilstein Registry Number Beilstein
99070 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
14976342 PubMed citation Europe PMC
15043430 PubMed citation Europe PMC
15790535 PubMed citation Europe PMC
17077549 PubMed citation Europe PMC
19013527 PubMed citation Europe PMC
Last Modified
25 February 2016