Canmetcon
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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:16:54 UTC
Update Date2019-01-11 19:48:28 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. (Wikipedia
Structure
Data?1547236108
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
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[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-12-one
Traditional Namecube root
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
DescriptionThis compound belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct Parent8-prenylated isoflavanones
Alternative Parents
Substituents
  • 8-prenylated isoflavanone
  • Rotenone or derivatives
  • Chromeno-3,4b-chromene
  • Rotenoid
  • Isoflavanol
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Benzofuran
  • Aryl alkyl ketone
  • Aryl ketone
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point163 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0002 mg/mL at 20 °CNot Available
LogP4.10Not Available
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
Polarizability42.06 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi3-2549000000-930d18ff5e2d26d23e39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0009000000-358453a180ad1eac44bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0129000000-cc8a296246aa7e1b7fecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03dm-0795000000-228bd7c35bed240b45adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ow-0698000000-a9e4b41be932783b0afdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ow-0698000000-8f6994cc1cf72104baf0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dm-0696000000-cbec904cb2f70ad2fab0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dl-0693000000-fb2d60cf107761a6c44dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dl-0693000000-5718e6cf640e3d715757View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dl-0693000000-0e5df9ae944ec77aec31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0129000000-36a830cd40ad8fbcdeeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004s-1359000000-7b6f697fe59d525d48f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r0-4931000000-2d664b8d3fd4ebfd86ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-fbc08106b7ba4d66b944View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0019000000-ac9b3c7e9dbdabbc9404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbj-0924000000-7060b1a64eec50bf9c96View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-3901000000-c340e02baee25cf6196bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012837
KNApSAcK IDC00002568
Chemspider ID6500
KEGG Compound IDC07593
BioCyc IDCPD-5741
BiGG IDNot Available
Wikipedia LinkCube root
METLIN IDNot Available
PubChem Compound6758
PDB IDNot Available
ChEBI ID28201
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.. .