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Showing Compound Rotenone (FDB012837)

Record Information
Version1.0
Creation date2010-04-08 22:10:23 UTC
Update date2019-11-26 03:07:41 UTC
Primary IDFDB012837
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRotenone
DescriptionWidely distrib. 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. Rotenone is found in jicama and pulses.
CAS Number83-79-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-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
[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, 9CIdb_source
5'beta-rotenoneChEBI
Derris, JMAFdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP2.3ALOGPS
logP3.32ChemAxon
logS-4.5ALOGPS
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
Chemical FormulaC23H22O6
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight394.4172
Monoisotopic Molecular Weight394.141638436
Classification
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

Route of exposure:

Biological location:

Source:

Role

Indirect biological role:

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.04%; H 5.62%; O 24.34%DFC
Melting PointMp 163°DFC
Boiling PointNot Available
Experimental Water Solubility0.0002 mg/mL at 20 oCAUGUSTIJN-BECKERS,PWM et al. (1994)
Experimental logP4.10HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -225 (C6H6)DFC
Spectroscopic UV Data295 (e 16980) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-3901000000-c340e02baee25cf6196b2014-09-20View Spectrum
Predicted GC-MSRotenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zi3-2549000000-930d18ff5e2d26d23e39Spectrum
Predicted GC-MSRotenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRotenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0009000000-358453a180ad1eac44bb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0129000000-cc8a296246aa7e1b7fec2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03dm-0795000000-228bd7c35bed240b45ad2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ow-0698000000-a9e4b41be932783b0afd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ow-0698000000-8f6994cc1cf72104baf02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dm-0696000000-cbec904cb2f70ad2fab02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dl-0693000000-fb2d60cf107761a6c44d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dl-0693000000-5718e6cf640e3d7157572017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dl-0693000000-0e5df9ae944ec77aec312017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03dl-4669000000-0fb03940864d95c2078a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-03dl-0693000000-33cf33e1c5d6e621df3a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-03dl-0693000000-209ca7e024f911e3b7d92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-1449000000-3bc2601b53c203b7fa832021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-01oy-0964000000-acfb0099b12ab168b4a82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0007-0910000000-7b2d8dce16788bdf77472021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0002-0129000000-64fb6c845a91bd3fb4b72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-9e8d4cec92e24203cdbd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03dm-0695000000-e9e1241f5910716f0c922021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03dm-0695000000-4af2f040a67e164c63252021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0129000000-36a830cd40ad8fbcdeee2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004s-1359000000-7b6f697fe59d525d48f92017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r0-4931000000-2d664b8d3fd4ebfd86ce2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-fbc08106b7ba4d66b9442017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0019000000-ac9b3c7e9dbdabbc94042017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbj-0924000000-7060b1a64eec50bf9c962017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
ChemSpider ID6500
ChEMBL IDCHEMBL429023
KEGG Compound IDC07593
Pubchem Compound ID6758
Pubchem Substance IDNot Available
ChEBI ID28201
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34436
CRC / DFC (Dictionary of Food Compounds) IDHMJ07-C:HMJ07-C
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002568
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDRotenone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.