(-)-cis-Rotenolone (CHEM028251)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:19:24 UTC
Update Date2016-11-09 01:18:39 UTC
Accession NumberCHEM028251
Identification
Common Name(-)-cis-Rotenolone
ClassSmall Molecule
Description(-)-cis-Rotenolone is found in jicama. (-)-cis-Rotenolone is isolated from Pachyrrhizus erosus (yam bean).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-cis-12a-HydroxyrotenoneHMDB
1,2,12,12a-tetrahydro-6a-Hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-(2R,6ar,12ar)-[1]benzopyrano[3,4-b]furo[2,3-H][1]benzopyran-6(6ah)-oneHMDB
12-HydroxyrotenoneHMDB
12alpha-HydroxyrotenoneHMDB
6a-beta,12a-beta-RotenoloneHMDB
6Ab,12ab-rotenoloneHMDB
RotenaloneHMDB
Rotenolon IHMDB
RotenoloneHMDB
Rotenolone IHMDB
6 alpha(beta),12 alpha(beta)-RotenoloneMeSH
Rotenolone, (2R-(2alpha,6aalpha,12aalpha))-isomerMeSH
Rotenolone, (2R-(2alpha,6abeta,12aalpha))-isomerMeSH
Rotenolone, (2R-(2alpha,6aalpha,12abeta))-isomerMeSH
Chemical FormulaC23H22O7
Average Molecular Mass410.417 g/mol
Monoisotopic Mass410.137 g/mol
CAS Registry Number509-96-6
IUPAC Name(1R,6R,13R)-13-hydroxy-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 Namerotenolone
SMILES[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=CC=C3O[C@H](CC3=C1O2)C(C)=C
InChI IdentifierInChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1
InChI KeyJFVKWCYZKMUTLH-AYPBNUJASA-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
  • 1-benzopyran
  • Chromane
  • Benzopyran
  • Coumaran
  • Aryl alkyl ketone
  • Aryl ketone
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Ketone
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Alcohol
  • 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 Solubility0.056 g/LALOGPS
logP2.4ALOGPS
logP2.73ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)11.08ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity106.96 m³·mol⁻¹ChemAxon
Polarizability42.8 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udj-2898000000-a911918046b993e78796Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0v4i-9420700000-d42a2e5be951b642755eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1223900000-9a1f17cd964abaa81aa8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-2394300000-b8d33d58c295207f77a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2930000000-7ebdad6df07b04059cf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0011900000-068963a903131042e2deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0059600000-b085e22dff915ed213c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-1933000000-acb18ae95eb8c0f59fb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-13ca06aa040c9821ae69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0325900000-33ff0fbbe9523120bd61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1869100000-793032f9edca87024cfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-cc474c0f71581fe9b76fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0115900000-866e3635b32607356e9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-3395000000-409148100e6d88cb50cdSpectrum
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 IDNot Available
HMDB IDHMDB0034145
FooDB IDFDB012420
Phenol Explorer IDNot Available
KNApSAcK IDC00002537
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID61491
ChEBI IDNot Available
PubChem Compound ID68184
Kegg Compound IDC10464
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.