Record Information
Version1.0
Creation date2010-04-08 22:05:29 UTC
Update date2020-02-24 19:10:35 UTC
Primary IDFDB002688
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name13alpha-Hydroxydolineone
Description13alpha-Hydroxydolineone 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. Thus, 13alpha-hydroxydolineone is considered to be a flavonoid lipid molecule. 13alpha-Hydroxydolineone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 13alpha-Hydroxydolineone has been detected, but not quantified in, jicama and pulses. This could make 13alpha-hydroxydolineone a potential biomarker for the consumption of these foods.
CAS Number28617-71-2
Structure
Thumb
Synonyms
SynonymSource
13a-HydroxydolineoneGenerator
13Α-hydroxydolineoneGenerator
12a-Hydroxydolineonedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.51 g/LALOGPS
logP2.08ALOGPS
logP1.91ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)11.03ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area87.36 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.75 m³·mol⁻¹ChemAxon
Polarizability34.33 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC19H12O7
IUPAC name1-hydroxy-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one
InChI IdentifierInChI=1S/C19H12O7/c20-18-10-3-9-1-2-22-12(9)5-13(10)26-17-7-23-14-6-16-15(24-8-25-16)4-11(14)19(17,18)21/h1-6,17,21H,7-8H2
InChI KeyHLEAVDSSZUIWQI-UHFFFAOYSA-N
Isomeric SMILESOC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O
Average Molecular Weight352.2944
Monoisotopic Molecular Weight352.058302738
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
  • Isoflavanone
  • Isoflavan
  • Furanochromone
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzodioxole
  • Benzofuran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Tertiary alcohol
  • Ketone
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.78%; H 3.43%; O 31.79%DFC
Melting PointMp 194-195° (180-181°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +137 (CHCl3)DFC
Spectroscopic UV Data338 (sh) (3.64) (EtOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-2913000000-506dee24db7b8cf3a618JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ds-9343200000-96d8036ba9a77c71c661JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-586b0b4a691c1edcb5c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-0619000000-7dcbda7eea674461b590JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1900000000-ebb97846d21913823d47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0109000000-128203575629f8eed5f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0409000000-4a49f6ba37c665e7bd7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1900000000-ba731628889bb1115477JSpectraViewer
ChemSpider ID24842945
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID13885696
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30756
CRC / DFC (Dictionary of Food Compounds) IDHFP50-R:CNC44-G
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00009582
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.