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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:16:54 UTC
Update Date2021-09-14 15:37:04 UTC
HMDB IDHMDB0034436
Secondary Accession Numbers
  • HMDB34436
Metabolite Identification
Common NameRotenone
DescriptionRotenone is found in jicama. Rotenone is widely distributed in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean).Rotenone is an odorless chemical that is used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the roots and stems of several plants such as the jicama vine plant. In mammals, including humans, it is linked to the development of Parkinson's disease.
Structure
Data?1563862563
Synonyms
ValueSource
(-)-cis-RotenoneChEBI
(-)-RotenoneChEBI
5'beta-RotenoneChEBI
[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)-oneChEBI
BarbascoChEBI
CanexChEBI
DactinolChEBI
DerrisChEBI
NoxfireChEBI
ParaderilChEBI
TubatoxinChEBI
5'b-RotenoneGenerator
5'Β-rotenoneGenerator
[2R-(2a,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)-oneGenerator
[2R-(2Α,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)-oneGenerator
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, 9ciHMDB
DerrinHMDB
Derris, jmafHMDB
Dri-kilHMDB
NicoulineHMDB
NoxfishHMDB
TubotoxinHMDB
Chemical FormulaC23H22O6
Average Molecular Weight394.4172
Monoisotopic Molecular Weight394.141638436
IUPAC Name(1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one
Traditional Name(1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one
CAS Registry Number83-79-4
SMILES
[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C
InChI Identifier
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
InChI KeyJUVIOZPCNVVQFO-HBGVWJBISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassRotenoids
Direct ParentRotenones
Alternative Parents
Substituents
  • Rotenone or derivatives
  • 8-prenylated isoflavanone
  • Isoflavanone
  • Isoflavan
  • Chromone
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Coumaran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Benzenoid
  • Ketone
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point163 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0002 mg/mL at 20 °CNot Available
LogP4.10Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker202.51630932474
[M+H]+Baker199.63430932474
[M-H]-Not Available202.516http://allccs.zhulab.cn/database/detail?ID=AllCCS00001451
[M+H]+Not Available196.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00001451
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP10(2.3) g/LALOGPS
logP10(3.32) g/LChemAxon
logS10(-4.5) g/LALOGPS
pKa (Strongest Acidic)11.8ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area63.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.71 m³·mol⁻¹ChemAxon
Polarizability42.07 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+194.19731661259
DarkChem[M-H]-193.80931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Rotenone[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C4737.8Standard polar33892256
Rotenone[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C3252.3Standard non polar33892256
Rotenone[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1([H])C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C3284.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rotenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi3-2549000000-930d18ff5e2d26d23e392017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rotenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rotenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-3901000000-c340e02baee25cf6196b2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone LC-ESI-QTOF , positive-QTOFsplash10-0002-0009000000-358453a180ad1eac44bb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone LC-ESI-QTOF , positive-QTOFsplash10-0002-0129000000-cc8a296246aa7e1b7fec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone LC-ESI-QTOF , positive-QTOFsplash10-03dm-0795000000-228bd7c35bed240b45ad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOFsplash10-01ow-0698000000-a9e4b41be932783b0afd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOFsplash10-01ow-0698000000-8f6994cc1cf72104baf02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOFsplash10-03dm-0696000000-cbec904cb2f70ad2fab02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOFsplash10-03dl-0693000000-fb2d60cf107761a6c44d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOFsplash10-03dl-0693000000-5718e6cf640e3d7157572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone LC-ESI-ITFT , positive-QTOFsplash10-03dl-0693000000-0e5df9ae944ec77aec312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone 20V, Negative-QTOFsplash10-03dl-4669000000-0fb03940864d95c2078a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone 55V, Positive-QTOFsplash10-03dl-0693000000-33cf33e1c5d6e621df3a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone 45V, Positive-QTOFsplash10-03dl-0693000000-209ca7e024f911e3b7d92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone 10V, Negative-QTOFsplash10-0006-1449000000-3bc2601b53c203b7fa832021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone 20V, Positive-QTOFsplash10-01oy-0964000000-acfb0099b12ab168b4a82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone 40V, Positive-QTOFsplash10-0007-0910000000-7b2d8dce16788bdf77472021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone 15V, Positive-QTOFsplash10-0002-0129000000-64fb6c845a91bd3fb4b72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone 10V, Positive-QTOFsplash10-0002-0009000000-9e8d4cec92e24203cdbd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone 20V, Positive-QTOFsplash10-03dm-0695000000-e9e1241f5910716f0c922021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rotenone 20V, Positive-QTOFsplash10-03dm-0695000000-4af2f040a67e164c63252021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotenone 10V, Positive-QTOFsplash10-0002-0129000000-36a830cd40ad8fbcdeee2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotenone 20V, Positive-QTOFsplash10-004s-1359000000-7b6f697fe59d525d48f92017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotenone 40V, Positive-QTOFsplash10-05r0-4931000000-2d664b8d3fd4ebfd86ce2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotenone 10V, Negative-QTOFsplash10-0006-0009000000-fbc08106b7ba4d66b9442017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotenone 20V, Negative-QTOFsplash10-0006-0019000000-ac9b3c7e9dbdabbc94042017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rotenone 40V, Negative-QTOFsplash10-0pbj-0924000000-7060b1a64eec50bf9c962017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11457
Phenol Explorer Compound IDNot Available
FooDB IDFDB012837
KNApSAcK IDC00002568
Chemspider ID6500
KEGG Compound IDC07593
BioCyc IDCPD-5741
BiGG IDNot Available
Wikipedia LinkRotenone
METLIN IDNot Available
PubChem Compound6758
PDB IDNot Available
ChEBI ID28201
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1280741
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Khar A, Ali AM, Begum Z, Pardhasaradhi BV, Varalakshmi C: Induction of apoptosis in AK-5 cells by rotenone involves participation of caspases. Indian J Biochem Biophys. 1999 Apr;36(2):77-81. [PubMed:10549166 ]
  2. Tapias V, Cannon JR, Greenamyre JT: Melatonin treatment potentiates neurodegeneration in a rat rotenone Parkinson's disease model. J Neurosci Res. 2010 Feb 1;88(2):420-7. doi: 10.1002/jnr.22201. [PubMed:19681169 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .