Rotenone
fo-255d7306b7a59f7f
Identity
- Type
- NeutralMolecule
- CAS
- 83-79-4
- EC
- 201-501-9
- Origin
- EF 3.1 hybrid_name_cas_v1
- Changes
- 59 across every transformer
Structure
This substance carries 2 candidate structures; the diagram is the first one RDKit could parse, not a settled answer.
What it is used for
2
Roles, not types. A substance bears as many as apply — sulfluramid is an
insecticide and an acaricide — and each is a class ChEBI curates, asserted
with ChEBI’s own has role. The narrow ones publish the broad
ones alongside them, so a substance filed as a herbicide is a pesticide
here too. See agricultural
chemicals for what the axis is and which classes are published.
| Role | Definition | Evidence |
|---|---|---|
| insecticide CHEBI:24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | ChEBI |
| pesticide CHEBI:25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | ChEBI |
Alternative labels
50- (-)-cis-rotenone
- (-)-rotenone
- (12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano[3,4-b]furano [2,3-h]chroman-6-one
- (2R,6aS,12aS)-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
- (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
- 5'beta-rotenone
- 5′β-Rotenone
- [1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aS,12aS)-
- [1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, [2R-(2α,6aα,12aα)]-
- [1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aαH)-one, 1,2,12,12aα-tetrahydro-2α-isopropenyl-8,9-dimethoxy-
- [2R-(2alpha,6aalpha,12aalpha)]-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
- barbasco
- canex
- Cenol Garden Dust
- CFT Legumine
- Chem Fish
- Chem-Mite
- Cube-Pulver
- Cuberol
- Curex flea duster
- dactinol
- Deril
- Derrin
- Derris
- Derris (insecticide)
- Dri-kil
- Fish Tox
- Fish Tox 5
- Green cross warble powder
- Liquid Derris
- MeSH ID: D012402
- Nicouline
- noxfire
- Noxfish
- paraderil
- Prenfish Toxicant
- Prentox Prenfish
- Prentox Prenfish Toxicant
- Ronone
- Rotacide
- Rotacide EC
- Rotena
- Rotenon
- Rotenox
- Rotocide
- Sinid
- TIFA Chem Fish
- Tox-R
- tubatoxin
- YuTengTong
Properties
| Property | Value |
|---|---|
| Elemental charge chemrof:elemental_charge | 0 |
| InChI2D key string chemrof:inchi2d_key_string | JUVIOZPCNVVQFO-HBGVWJBISA-N |
| InChI2D string chemrof:inchi2d_string | 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 |
| Isomeric SMILES string chemrof:isomeric_smiles_string | C=C(C)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(OC)c(OC)cc4[C@@H]2C3=O)O1 |
| IUPAC name chemrof: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 |
| Molecular formula chemrof:molecular_formula | C23H22O6 |
| Molecular mass chemrof:molecular_mass | 394.423 |
| Monoisotopic mass chemrof:monoisotopic_mass | 394.141638, 394.14164 |
| SMILES string chemrof:smiles_string | C=C(C)C1Cc2c(ccc3c2OC2COc4cc(OC)c(OC)cc4C2C3=O)O1 |
Known URLs
45Where else this substance is described. Collected while the pipeline resolved it — from ChEBI's cross-references, from PubChem's identifier list, and from the CAS number — so a link here is a record the merge actually read, not a search it suggests.
| Resource | URL | Recorded by |
|---|---|---|
| bpdb | bpdb:587 | enrich_references.chebi_xrefs |
| CAS Common Chemistry | https://commonchemistry.cas.org/detail?cas_rn=83-79-4 | enrich_references.chebi_xrefs |
| cdc.gov | https://www.cdc.gov/niosh-rtecs/DJ2AB980.html | enrich_references.pubchem_identifier_url |
| ChEBI | https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28201 | enrich_references.chebi_id_link |
| chem.echa.europa.eu | https://chem.echa.europa.eu/100.001.365 | enrich_references.pubchem_identifier_url |
| chemicalsafety.ilo.org | https://chemicalsafety.ilo.org/dyn/icsc/showcard.display?p_card_id=0944 | enrich_references.pubchem_identifier_url |
| comptox.epa.gov | https://comptox.epa.gov/dashboard/DTXSID6021248 | enrich_references.pubchem_identifier_url |
| DrugBank | https://go.drugbank.com/drugs/DB11457 | enrich_references.chebi_xrefs |
| drugbank.ca | https://www.drugbank.ca/drugs/DB11457 | enrich_references.pubchem_identifier_url |
| dtp.cancer.gov | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=26258 | enrich_references.pubchem_identifier_url |
| dtp.cancer.gov | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=8505 | enrich_references.pubchem_identifier_url |
| ebi.ac.uk | https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL429023 | enrich_references.pubchem_identifier_url |
| foodb.food | foodb.food:FDB012837 | enrich_references.chebi_xrefs |
| glycosmos.org | https://glycosmos.org/glycans/show/G26488SP | enrich_references.pubchem_identifier_url |
| gsrs.ncats.nih.gov | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/03L9OT429T | enrich_references.pubchem_identifier_url |
| HMDB | https://hmdb.ca/metabolites/HMDB0034436 | enrich_references.chebi_xrefs |
| jglobal.jst.go.jp | http://jglobal.jst.go.jp/en/redirect?Nikkaji_No=J108.000H | enrich_references.pubchem_identifier_url |
| KEGG | https://www.genome.jp/entry/C07593 | enrich_references.chebi_xrefs |
| kegg.jp | https://www.kegg.jp/entry/C07593 | enrich_references.pubchem_identifier_url |
| knapsack | knapsack:C00002568 | enrich_references.chebi_xrefs |
| lincs.smallmolecule | lincs.smallmolecule:LSM-5260 | enrich_references.chebi_xrefs |
| LIPID MAPS | https://www.lipidmaps.org/databases/lmsd/LMPK12060007 | enrich_references.chebi_xrefs |
| lipidmaps.org | https://lipidmaps.org/databases/lmsd/LMPK12060007 | enrich_references.pubchem_identifier_url |
| metabolomicsworkbench.org | https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=22653 | enrich_references.pubchem_identifier_url |
| ncithesaurus.nci.nih.gov | https://ncithesaurus.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=ncit&code=C76087 | enrich_references.pubchem_identifier_url |
| patent | patent:CN102007944 | enrich_references.chebi_xrefs |
| patent | patent:CN102090406 | enrich_references.chebi_xrefs |
| pdb-ccd | pdb-ccd:970 | enrich_references.chebi_xrefs |
| platform.opentargets.org | https://platform.opentargets.org/drug/CHEMBL429023 | enrich_references.pubchem_identifier_url |
| PubChem | https://pubchem.ncbi.nlm.nih.gov/compound/6758 | enrich_references.pubchem_compound |
| PubChem | https://pubchem.ncbi.nlm.nih.gov/erg/#2588 | enrich_references.pubchem_identifier_url |
| PubChem | https://pubchem.ncbi.nlm.nih.gov/substance/?source=niaid&sourceid=002703 | enrich_references.pubchem_identifier_url |
| PubMed | https://pubmed.ncbi.nlm.nih.gov/14976342 | enrich_references.chebi_xrefs |
| PubMed | https://pubmed.ncbi.nlm.nih.gov/15043430 | enrich_references.chebi_xrefs |
| PubMed | https://pubmed.ncbi.nlm.nih.gov/15790535 | enrich_references.chebi_xrefs |
| PubMed | https://pubmed.ncbi.nlm.nih.gov/17077549 | enrich_references.chebi_xrefs |
| PubMed | https://pubmed.ncbi.nlm.nih.gov/19013527 | enrich_references.chebi_xrefs |
| PubMed | https://pubmed.ncbi.nlm.nih.gov/32972993 | enrich_references.chebi_xrefs |
| PubMed | https://pubmed.ncbi.nlm.nih.gov/33402167 | enrich_references.chebi_xrefs |
| PubMed | https://pubmed.ncbi.nlm.nih.gov/33901458 | enrich_references.chebi_xrefs |
| PubMed | https://pubmed.ncbi.nlm.nih.gov/33961406 | enrich_references.chebi_xrefs |
| reaxys | reaxys:99070 | enrich_references.chebi_xrefs |
| vsdb | vsdb:587 | enrich_references.chebi_xrefs |
| wikidata.org | https://www.wikidata.org/wiki/Q412388 | enrich_references.pubchem_identifier_url |
| Wikipedia | https://en.wikipedia.org/wiki/Rotenone | enrich_references.chebi_xrefs |
Elementary flows
14| Flow | Context | Source | Unit | CFs |
|---|---|---|---|---|
| e2fb2bca-6555-11dd-ad8b-0800200c9a66 | Environmental → Air → Aircraft cruise height | EF 3.1 | kg | 4 |
| 4d9a8790-3ddd-11dd-9abc-0050c2490048 | Environmental → Air → Ground level → Urban (>1000 people/square mile) | EF 3.1 | kg | 4 |
| 33155585-907f-43aa-bd00-fde57304e854 | Environmental → Air → Indoor | EF 3.1 | kg | 4 |
| 4d9a8790-3ddd-11dd-9abb-0050c2490048 | Environmental → Air → Long-term | EF 3.1 | kg | 0 |
| fe0acd60-3ddc-11dd-a1da-0050c2490048 | Environmental → Air → Medium stack, <150 meters → Rural (<1000 people/square mile) | EF 3.1 | kg | 4 |
| 4d9a8790-3ddd-11dd-9aba-0050c2490048 | Environmental → Air → Unknown | EF 3.1 | kg | 4 |
| 4d9a8790-3ddd-11dd-9ab8-0050c2490048 | Environmental → Ground → Agricultural | EF 3.1 | kg | 4 |
| fe0acd60-3ddc-11dd-a1af-0050c2490048 | Environmental → Ground → Non-agricultural | EF 3.1 | kg | 4 |
| 63a337c3b7649524767a036090cb75aa2ec34664 | Environmental → Ground → Silvicultural | ecoinvent algorithm addition | kg | 0 |
| 4d9a8790-3ddd-11dd-9ab9-0050c2490048 | Environmental → Ground → Unknown | EF 3.1 | kg | 4 |
| fe0acd60-3ddc-11dd-a1dc-0050c2490048 | Environmental → Water → Long-term | EF 3.1 | kg | 0 |
| fe0acd60-3ddc-11dd-a1b0-0050c2490048 | Environmental → Water → Ocean | EF 3.1 | kg | 4 |
| fe0acd60-3ddc-11dd-a1db-0050c2490048 | Environmental → Water → Surface water | EF 3.1 | kg | 4 |
| fe0acd60-3ddc-11dd-a1dd-0050c2490048 | Environmental → Water → Unknown | EF 3.1 | kg | 4 |
History
Everything that changed this substance (59 changes)
Full record
Flow object JSON
{
"flow_object_id": "fo-255d7306b7a59f7f",
"prefLabel": [
{
"@value": "Rotenone",
"@language": "en",
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}
}
],
"altLabel": [
{
"@value": "(-)-cis-rotenone",
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},
{
"@value": "(-)-rotenone",
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],
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}
},
{
"@value": "(12aS,6aS,2R)-8,9-dimethoxy-2-(1-methylvinyl)-1,2-dihydrochromano[3,4-b]furano [2,3-h]chroman-6-one",
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],
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}
},
{
"@value": "(2R,6aS,12aS)-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",
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},
{
"@value": "(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",
"@language": "en",
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},
{
"@value": "5'beta-rotenone",
"@language": "en",
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}
},
{
"@value": "5′β-Rotenone",
"@language": "en",
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},
{
"@value": "[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aS,12aS)-",
"@language": "en",
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},
{
"@value": "[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, [2R-(2α,6aα,12aα)]-",
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],
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}
},
{
"@value": "[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aαH)-one, 1,2,12,12aα-tetrahydro-2α-isopropenyl-8,9-dimethoxy-",
"@language": "en",
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],
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}
},
{
"@value": "[2R-(2alpha,6aalpha,12aalpha)]-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",
"@language": "en",
"@lang": "en",
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}
},
{
"@value": "barbasco",
"@language": "en",
"@lang": "en",
"provenance": {
"prov:wasGeneratedBy": "chebi_altlabels",
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}
},
{
"@value": "canex",
"@language": "en",
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"provenance": {
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],
"prov:wasDerivedFrom": "chebi synonym match"
}
},
{
"@value": "Cenol Garden Dust",
"@language": "en",
"@lang": "en",
"provenance": {
"prov:wasGeneratedBy": "consensus_match",
"prov:wasAttributedTo": "consensus-flow-list",
"prov:hadPrimarySource": [
"CAS:83-79-4",
"EF 3.1",
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],
"prov:wasDerivedFrom": "common chemistry CAS lookup"
}
},
{
"@value": "CFT Legumine",
"@language": "en",
"@lang": "en",
"provenance": {
"prov:wasGeneratedBy": "consensus_match",
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"CAS:83-79-4",
"EF 3.1",
"https://commonchemistry.cas.org/detail?cas_rn=83-79-4"
],
"prov:wasDerivedFrom": "common chemistry CAS lookup"
}
},
{
"@value": "Chem Fish",
"@language": "en",
"@lang": "en",
"provenance": {
"prov:wasGeneratedBy": "consensus_match",
"prov:wasAttributedTo": "consensus-flow-list",
"prov:hadPrimarySource": [
"CAS:83-79-4",
"EF 3.1",
"https://commonchemistry.cas.org/detail?cas_rn=83-79-4"
],
"prov:wasDerivedFrom": "common chemistry CAS lookup"
}
},
{
"@value": "Chem-Mite",
"@language": "en",
"@lang": "en",
"provenance": {
"prov:wasGeneratedBy": "consensus_match",
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"CAS:83-79-4",
"EF 3.1",
"https://commonchemistry.cas.org/detail?cas_rn=83-79-4"
],
"prov:wasDerivedFrom": "common chemistry CAS lookup"
}
},
{
"@value": "Cube-Pulver",
"@language": "en",
"@lang": "en",
"provenance": {
"prov:wasGeneratedBy": "consensus_match",
"prov:wasAttributedTo": "consensus-flow-list",
"prov:hadPrimarySource": [
"CAS:83-79-4",
"EF 3.1",
"https://commonchemistry.cas.org/detail?cas_rn=83-79-4"
],
"prov:wasDerivedFrom": "common chemistry CAS lookup"
}
},
{
"@value": "Cuberol",
"@language": "en",
"@lang": "en",
"provenance": {
"prov:wasGeneratedBy": "consensus_match",
"prov:wasAttributedTo": "consensus-flow-list",
"prov:hadPrimarySource": [
"CAS:83-79-4",
"EF 3.1",
"https://commonchemistry.cas.org/detail?cas_rn=83-79-4"
],
"prov:wasDerivedFrom": "common chemistry CAS lookup"
}
},
{
"@value": "Curex flea duster",
"@language": "en",
"@lang": "en",
"provenance": {
"prov:wasGeneratedBy": "consensus_match",
"prov:wasAttributedTo": "consensus-flow-list",
"prov:hadPrimarySource": [
"CAS:83-79-4",
"EF 3.1",
"https://commonchemistry.cas.org/detail?cas_rn=83-79-4"
],
"prov:wasDerivedFrom": "common chemistry CAS lookup"
}
},
{
"@value": "dactinol",
"@language": "en",
"@lang": "en",
"provenance": {
"prov:wasGeneratedBy": "chebi_altlabels",
"prov:wasAttributedTo": "consensus-flow-list",
"prov:hadPrimarySource": [
"EF 3.1",
"http://purl.obolibrary.org/obo/CHEBI_28201"
],
"prov:wasDerivedFrom": "chebi synonym match"
}
},
{
"@value": "Deril",
"@language": "en",
"@lang": "en",
"provenance": {
"prov:wasGeneratedBy": "consensus_match",
"prov:wasAttributedTo": "consensus-flow-list",
"prov:hadPrimarySource": [
"CAS:83-79-4",
"EF 3.1",
"https://commonchemistry.cas.org/detail?cas_rn=83-79-4"
],
"prov:wasDerivedFrom": "common chemistry CAS lookup"
}
},
{
"@value": "Derrin",
"@language": "en",
"@lang": "en",
"provenance": {
"prov:wasGeneratedBy": "consensus_match",
"prov:wasAttributedTo": "consensus-flow-list",
"prov:hadPrimarySource": [
"CAS:83-79-4",
"EF 3.1",
"https://commonchemistry.cas.org/detail?cas_rn=83-79-4"
],
"prov:wasDerivedFrom": "common chemistry CAS lookup"
}
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