rotenone (Q412388)

Gene Ontology release 2019-11-16

has use

insecticide

1 reference

Medical Subject Headings

15 March 2018

Rotenone Structural Formula V.1.svg
718 × 533; 35 KB

1 reference

0 references

1 reference

(1S,6S,13R)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

stereoisomer of

2 references

(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)-, (2S-(2alpha,6aalpha,12aalpha))-

inferred from InChI

2 references

2 references

2 references

inferred from InChI

chemical formula

C₂₃H₂₂O₆

1 reference

rotenone (English)

19 November 2016

CC(=C)C1CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC

1 reference

rotenone (English)

19 November 2016

CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC

1 reference

rotenone (English)

19 November 2016

1.27±0.01 gram per cubic centimetre

temperature

20±1 degree Celsius

1 reference

melting point

330±1 degree Fahrenheit

1 reference

boiling point

215±5 degree Celsius

under pressure

0.5 millimetre of mercury

1 reference

English Wikipedia

vapor pressure

0.00004±0.00001 millimetre of mercury

temperature

68±1 degree Fahrenheit

criterion used

maximum

1 reference

time-weighted average exposure limit

NIOSH Pocket Guide ID

0548

0 references

5±1 milligram per cubic metre

applies to jurisdiction

United States

duration

10±1 hour

1 reference

immediately dangerous to life or health

2,500±100 milligram per cubic metre

1 reference

found in taxon

Pachyrhizus erosus

2 references

Rotenone isolated from Pachyrhizus erosus displays cytotoxicity and genotoxicity in K562 cells.

Constituents of the Insecticidal Resin of the Yam Bean (Pachyrrhizus erosus)1

Tephrosia purpurea

2 references

Flavonoids of Tephrosia polyphylla

A new epoxyflavanone from tephrosia hamiltonii1

Tephrosia vogelii

1 reference

Production of rotenoids by heterotrophic and photomixotrophic cell cultures of tephrosia vogelii

Tephrosia pentaphylla

1 reference

Flavonoids and isoflavonoids from Tephrosia fulvinervis and Tephrosia pentaphylla

Piscidia piscipula

7 references

New Rotenoids from the Root Bark of Jamaican Dogwood (Piscidia erythrina L.)

Some New Constituents of Piscidia erythrina L.

Two isoflavones from Piscidia erythrina

Isoflavonoids from the Root Bark of Piscidia erythrina and a Note on the Structure of Piscidone

Fish Poisons from Ichthyomethia Piscipula. I

Über die Inhaltsstoffe vonPiscidia eryfhrina L

The extractives of piscidia erythrina L.—III

Millettia ferruginea

1 reference

C-prenylated isoflavones from Millettia ferruginea

Tephrosia leiocarpa

1 reference

Flavanones fromTephrosia leiocarpa

Derris trifoliata

5 references

Cancer chemopreventive activity of rotenoids from Derris trifoliata

7a-O-methyldeguelol, a modified rotenoid with an open ring-C, from the roots of Derris trifoliata

Cytotoxic rotenoloids from the stems of Derris trifoliata

Two unusual rotenoid derivatives, 7a-O-methyl-12a-hydroxydeguelol and spiro-13-homo-13-oxaelliptone, from the seeds of Derris trifoliata

Derris malaccensis

2 references

Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents

Millettia

1 reference

Prenylated isoflavonoids from Millettia pervilleana

Mundulea chapelieri

2 references

Cytotoxic compounds from Mundulea chapelieri from the Madagascar Rainforest.

Cytotoxic Compounds from Mundulea chapelieri from the Madagascar Rainforest

Derris elliptica

5 references

Antifeedants in Cyperaceae: coumaran and quinones from Cyperus spp.

NMR investigations of rotenoids

Untersuchung ueber die Wurzel von Derris elliptica Benth. I.

Zur Kenntnis der Bestandteile einiger Derris-Arten

Derris brevipes

1 reference

Chemical investigation of Indian fruits

Millettia rubiginosa

1 reference

Chemical investigation of Indian fruits

Lonchocarpus salvadorensis

2 references

Rotenoids of Lonchocarpus salvadorensis: Their effectiveness in protecting seeds against bruchid predation

Rotenoids of Lonchocarpus salvadorensis: Their effectiveness in protecting seeds against bruchid predation

Tephrosia procumbens

1 reference

Flavonoids of Tephrosia procumbens—revised structure for praecansone A and conformation of praecansone B

Amorpha fruticosa

2 references

Enzymic oxidative modification of prenyl groups. The biosynthetic origins of the E-ring systems of rotenone and amorphigenin

Biosynthesis of rotenone and amorphigenin. Study of the origins of isopropenyl-substituted dihydrofuran E-rings using isotopically labelled late precursors

Neorautanenia mitis

1 reference

Rautandiols A and B, pterocarpans and cytotoxic constituents from Neorautanenia mitis

Antheroporum pierrei

1 reference

Pierreiones A−D, Solid Tumor Selective Pyranoisoflavones and Other Cytotoxic Constituents from Antheroporum pierrei

Erycibe expansa

1 reference

Structures of new flavonoids, erycibenins D, E, and F, and NO production inhibitors from Erycibe expansa originating in Thailand

Millettia pachycarpa

1 reference

Rotenoids from roots of Millettia pachycarpa

Tephrosia interrupta

1 reference

Flavonoids from Tephrosia aequilata

Tephrosia linearis

1 reference

Flavonoids from Tephrosia aequilata

Millettia pachyloba

1 reference

Cytotoxic prenylated isoflavone and bipterocarpan from Millettia pachyloba

Pachyrrhizus erosus

1 reference

Constituents of the Insecticidal Resin of the Yam Bean (Pachyrrhizus erosus)1

Spatholobus parviflorus

1 reference

Rotenone in a Species of Spatholobus

Tephrosia macropoda

1 reference

Occurrence of Rotenone in Tephrosia macropoda Harv

Tephrosia strigosa

1 reference

Occurrence of Rotenoids inTephrosia strigosa

Tephrosia villosa

1 reference

New C-6 oxygenated rotenoids from tephrosia villosa -- villosin, villosone, villol and villinol

Deguelia urucu

1 reference

Deguelia negrensis

1 reference

Estudo químico de Derris negrensis

Tephrosia cinerea

1 reference

Flavonoids of Tephrosia procumbens—revised structure for praecansone A and conformation of praecansone B

Lonchocarpus nicou

1 reference

Lonchocarpene, a Stilbene, and Lonchocarpusone, an Isoflavone: Two New Pyranopolyphenols from Lonchocarpus nicou Roots

Pachyrhizus tuberosus

1 reference

Flavonoids and 3-phenylcoumarins from the seeds of Pachyrhizus tuberosus

Arabidopsis thaliana

1 reference

Functional characterization of the two ferrochelatases in Arabidopsis thaliana.

Valeriana officinalis

1 reference

Valeriana officinalis attenuates the rotenone-induced toxicity in Drosophila melanogaster

Lonchocarpus chiricanus

1 reference

Five new prenylated stilbenes from the root bark of Lonchocarpus chiricanus

Derris montana

2 references

Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents

Lonchocarpus heptaphyllus

1 reference

Lonchocarpene, a Stilbene, and Lonchocarpusone, an Isoflavone: Two New Pyranopolyphenols from Lonchocarpus nicou Roots

Lonchocarpus utilis

3 references

Lonchocarpene, a Stilbene, and Lonchocarpusone, an Isoflavone: Two New Pyranopolyphenols from Lonchocarpus nicou Roots

Cubé resin insecticide: identification and biological activity of 29 rotenoid constituents

Anticancer action of cubé insecticide: Correlation for rotenoid constituents between inhibition of NADH:ubiquinone oxidoreductase and induced ornithine decarboxylase activities

Derris

1 reference

Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents

Tephrosia candida

1 reference

Analysis of Rotenoids by High Temperature High Resolution Gas Chromatography-Mass Spectrometry

Lonchocarpus

1 reference

Cytotoxic flavonoids from the stem bark of Lonchocarpus aff. fluvialis.

mass

394.142 dalton

1 reference

rotenone (English)

5 October 2016

1 reference

subject has role

uncoupling agents

1 reference

Medical Subject Headings

15 March 2018

0 references

Rotenone

0 references

Identifiers

GND ID

4834738-3

Dewey Decimal Classification

Rotenon

0 references

615.952

1 reference

Integrated Authority File

639.977

1 reference

Integrated Authority File

668.651

1 reference

Integrated Authority File

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

1 reference

rotenone (English)

19 November 2016

2 references

rotenone (English)

19 November 2016

ChEBI release 2020-09-01

CAS Registry Number

83-79-4

2 references

rotenone (English)

19 November 2016

https://commonchemistry.cas.org/detail?cas_rn=83-79-4

9 April 2021

1 reference

Rotenone (English)

5 October 2016

2 references

rotenone (English)

19 November 2016

Reaxys registry number

99070

1 reference

rotenone (English)

5 October 2016

mapping relation type

2 references

ROTENONE (English)

19 November 2016

International Chemical Identifier

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

1 reference

ROTENONE (English)

19 November 2016

2 references

MSBNK-MPI_for_Chemical_Ecology-CE000116

1 reference

MassBank accession ID

0 references

MSBNK-MPI_for_Chemical_Ecology-CE000117

0 references

MSBNK-MPI_for_Chemical_Ecology-CE000118

0 references

MSBNK-MPI_for_Chemical_Ecology-CE000119

0 references

MSBNK-MPI_for_Chemical_Ecology-CE000120

0 references

MSBNK-MPI_for_Chemical_Ecology-CE000121

0 references

MSBNK-MPI_for_Chemical_Ecology-CE000122

0 references

MSBNK-IPB_Halle-PB005741

0 references

MSBNK-IPB_Halle-PB005742

0 references

MSBNK-IPB_Halle-PB005743

0 references

SPLASH

splash10-0002-0129000000-cc8a296246aa7e1b7fec

0 references

splash10-03dm-0795000000-228bd7c35bed240b45ad

0 references

splash10-01ow-0698000000-a9e4b41be932783b0afd

0 references

splash10-01ow-0698000000-8f6994cc1cf72104baf0

0 references

splash10-03dm-0696000000-cbec904cb2f70ad2fab0

0 references

splash10-03dl-0693000000-fb2d60cf107761a6c44d

0 references

splash10-03dl-0693000000-5718e6cf640e3d715757

0 references

splash10-03dl-0693000000-0e5df9ae944ec77aec31

0 references

splash10-0002-0009000000-37153913c174d9ad4f88

0 references

splash10-0gvn-0922000000-8d6e8ab5ca8b9e912d53

0 references

splash10-01ow-0932000000-cef337f3927fbf003e5b

0 references

splash10-01ow-0933000000-48bc9bbc819720c342ab

0 references

splash10-014i-0001900000-e6d2ca662fa3540b464f

0 references

splash10-0006-3901000000-c340e02baee25cf6196b

0 references

0 references

0 references

DJ2800000

0 references

0 references

1 reference

Hazardous Substances Data Bank

28 October 2019

ROTENONE (English)

10 May 2021

2 references

Mapping file of InChIStrings, InChIKeys and DTXSIDs for the EPA CompTox Dashboard

DSSTOX compound identifier

0 references

0 references

0 references

1 reference

rotenone (English)

ECHA Substance Infocard ID

19 November 2016

100.001.365

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.001.365

27 December 2018

OSHA Occupational Chemical Database ID

(2R,6aS,12aS)-1,2,6,6a,12,12a-hexahydro-2-isopropenyl-8,9-dimethoxychromeno[3,4-b]furo[2,3-h]chromen-6-one (English)

quotation

CAS no.: 83-79-4 (English)

718

0 references

PesticideInfo chemical ID

0 references

Rotenone

1 reference

D03.383.663.283.266.450.400.843

Medical Subject Headings

14 March 2018

broader concept

isoflavone

0 references

D03.633.100.150.266.450.400.843

0 references

heterocyclic compounds, 4 or more rings

0 references

RxNorm CUI

1366666

1 reference

rotenone (English)

19 November 2016

1 reference

Human Metabolome Database ID

HMDB0034436

2 references

1 reference

rotenone (English)

5 October 2016

2 references

rotenone (English)

19 November 2016

0 references

1 reference

Encyclopædia Britannica Online ID

0 references

0 references

science/rotenone

Encyclopedia of China (Third Edition) old ID (2021)

rotenone

0 references

0 references

1 reference

28 October 2013

Gran Enciclopèdia Catalana ID

rotenona

0 references

Gran Enciclopèdia Catalana ID (former scheme)

0140177

0 references

Great Norwegian Encyclopedia ID

rotenon

0 references

HCIS ID

2385

0 references

Microsoft Academic ID (discontinued)

0 references

1 reference

26 January 2022

https://docs.openalex.org/download-snapshot/snapshot-data-format

PM20 ware ID

232771

Rotenon

0 references

Römpp online ID

RD-18-01852

1 reference

inferred by common MeSH mappings on source and on Wikidata

1 reference

UMLS 2023

24 May 2023

WordNet 3.1 Synset ID

15037045-n

1 reference

Encyclopedia of China (Third Edition) ID (2026)

GF WordNet

1G2I2