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CHEBI:28201 - rotenone
| Formula | C23H22O6 |
| Net Charge | 0 |
| Average Mass | 394.423 |
| Monoisotopic Mass | 394.14164 |
| SMILES | [H][C@]1(C(=C)C)Cc2c(ccc3c2O[C@]2([H])COc4cc(OC)c(OC)cc4[C@]2([H])C3=O)O1 |
| 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 |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Derris elliptica (ncbitaxon:56063) | - | DOI (10.1016/S0040-4020(01)93394-0) | |
| Mundulea chapelieri (IPNI:20004737-1) | |||
| flower (BTO:0000469) | PubMed (15043430) | ||
| leaf (BTO:0000713) | PubMed (15043430) | ||
| bark (BTO:0001301) | PubMed (15043430) | ||
| Erycibe expansa (IPNI:267866-1) | stem (BTO:0001300) | PubMed (17077549) | |
| Antheroporum pierrei (IPNI:474590-1) | |||
| leaf (BTO:0000713) | PubMed (21452840) | Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1) | |
| twig (BTO:0001411) | PubMed (21452840) | Dried leaves and twigs were extracted with CH2Cl2/MeOH (1:1) |
| 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: | phytogenic insecticide An insecticide compound naturally occurring in plants. 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. |
| 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 |
|---|---|
| Rotenone | KEGG COMPOUND |
| (−)-rotenone | ChemIDplus |
| (−)-cis-rotenone | ChemIDplus |
| canex | ChemIDplus |
| 5'β-rotenone | NIST Chemistry WebBook |
| barbasco | ChemIDplus |
| Manual Xrefs | Databases |
|---|---|
| C07593 | KEGG COMPOUND |
| Rotenone | Wikipedia |
| LMPK12060007 | LIPID MAPS |
| CN102090406 | Patent |
| CN102007944 | Patent |
| C00002568 | KNApSAcK |
| LSM-5260 | LINCS |
| 587 | VSDB |
| 587 | BPDB |
| 970 | PDBeChem |
| DB11457 | DrugBank |
| HMDB0034436 | HMDB |
| FDB012837 | FooDB |
| Citations |
|---|