Record Information
Version1.0
Creation date2010-04-08 22:10:09 UTC
Update date2019-11-26 03:06:44 UTC
Primary IDFDB012420
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-cis-Rotenolone
Description(-)-cis-Rotenolone 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 (-)-cis-Rotenolone has been detected, but not quantified in, jicamas (Pachyrhizus erosus) and pulses. This could make (-)-cis-rotenolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (-)-cis-Rotenolone.
CAS Number509-96-6
Structure
Thumb
Synonyms
SynonymSource
(-)-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
[1]Benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-6a-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aR,12aR)-manual
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
12a-Hydroxyrotenonebiospider
6ab,12ab-Rotenolonebiospider
Rotenolone; (-)-cis-formdb_source
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC23H22O7
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
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
Isomeric 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
Average Molecular Weight410.4166
Monoisotopic Molecular Weight410.136553058
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
  • 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.31%; H 5.40%; O 27.29%DFC
Melting PointMp 91-92° (88°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -190.1 (CHCl3) (-145)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(-)-cis-Rotenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udj-2898000000-a911918046b993e78796Spectrum
Predicted GC-MS(-)-cis-Rotenolone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0v4i-9420700000-d42a2e5be951b642755eSpectrum
Predicted GC-MS(-)-cis-Rotenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1223900000-9a1f17cd964abaa81aa8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-2394300000-b8d33d58c295207f77a3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2930000000-7ebdad6df07b04059cf4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0011900000-068963a903131042e2deSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0059600000-b085e22dff915ed213c1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-1933000000-acb18ae95eb8c0f59fb9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-13ca06aa040c9821ae69Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0325900000-33ff0fbbe9523120bd61Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1869100000-793032f9edca87024cfdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-cc474c0f71581fe9b76fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0115900000-866e3635b32607356e9cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-3395000000-409148100e6d88cb50cdSpectrum
NMRNot Available
ChemSpider ID61491
ChEMBL IDCHEMBL240545
KEGG Compound IDC10464
Pubchem Compound ID68184
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34145
CRC / DFC (Dictionary of Food Compounds) IDHGV28-B:HGV16-W
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002537
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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.