Cycloseychellene (CHEM030457)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:54:20 UTC
Update Date2016-11-09 01:19:04 UTC
Accession NumberCHEM030457
Identification
Common NameCycloseychellene
ClassSmall Molecule
DescriptionA member of the class of rotenones that consists of 1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one substituted at position 2 by a prop-1-en-2-yl group and at positions 8 and 9 by methoxy groups (the 2R,6aS,12aS-isomer). A non-systemic insecticide, it is the principal insecticidal constituent of derris (the dried rhizome and root of Derris elliptica).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 FormulaC15H24
Average Molecular Mass204.351 g/mol
Monoisotopic Mass204.188 g/mol
CAS Registry Number52617-34-2
IUPAC Name4,7,8,11-tetramethyltetracyclo[5.4.0.0³,⁵.0⁴,⁸]undecane
Traditional Name4,7,8,11-tetramethyltetracyclo[5.4.0.0³,⁵.0⁴,⁸]undecane
SMILESCC1CCC2(C)C3(C)C4CC2(C)C1CC34
InChI IdentifierInChI=1S/C15H24/c1-9-5-6-14(3)13(2)8-12-11(7-10(9)13)15(12,14)4/h9-12H,5-8H2,1-4H3
InChI KeyXPWRIXBORAHMCD-UHFFFAOYSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00042 g/LALOGPS
logP4.47ALOGPS
logP3.74ChemAxon
logS-5.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity62.86 m³·mol⁻¹ChemAxon
Polarizability25.36 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-3900000000-2b9c1013929c318bce4aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-98b8e4eab8cd946d233cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1490000000-7a725e3ea16e1b28ba40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06te-3900000000-d72662a16adb4f83c184Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d0fe5ed0bbcfa60c303cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-829ffa2a496cae88f4caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fe0-1920000000-f32b62ce5cffd0ea4d7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-c084f3d998cc56a199d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0590000000-e270a4e16b089b4c94c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-0960000000-75a6df425fb300f2e2b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11457
HMDB IDHMDB0034436
FooDB IDFDB012837
Phenol Explorer IDNot Available
KNApSAcK IDC00002568
BiGG IDNot Available
BioCyc IDCPD-5741
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRotenone
Chemspider ID6500
ChEBI ID28201
PubChem Compound ID6758
Kegg Compound IDC07593
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14976342
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15043430
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15790535
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17077549
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19013527
6. 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.
7. 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.
8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.