You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:56:11 UTC
Update Date2019-07-23 06:15:17 UTC
HMDB IDHMDB0034141
Secondary Accession Numbers
  • HMDB34141
Metabolite Identification
Common Name12alpha-Hydroxyerosone
Description12alpha-Hydroxyerosone 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, 12alpha-hydroxyerosone is considered to be a flavonoid lipid molecule. 12alpha-Hydroxyerosone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 12alpha-hydroxyerosone has been detected, but not quantified in, jicama and pulses. This could make 12alpha-hydroxyerosone a potential biomarker for the consumption of these foods.
Structure
Data?1563862517
Synonyms
ValueSource
12a-HydroxyerosoneGenerator
12Α-hydroxyerosoneGenerator
6a,13a-Dihydro-13a-hydroxy-2,3-dimethoxy[1]benzopyrano[3,4-b]furo[3,2-g][1]benzopyran-13(6H)-one, 9ciHMDB
Chemical FormulaC20H16O7
Average Molecular Weight368.3368
Monoisotopic Molecular Weight368.089602866
IUPAC Name13-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-12-one
Traditional Name13-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-12-one
CAS Registry Number66322-32-5
SMILES
COC1=C(OC)C=C2C(OCC3OC4=C(C=C5C=COC5=C4)C(=O)C23O)=C1
InChI Identifier
InChI=1S/C20H16O7/c1-23-16-6-12-15(8-17(16)24-2)26-9-18-20(12,22)19(21)11-5-10-3-4-25-13(10)7-14(11)27-18/h3-8,18,22H,9H2,1-2H3
InChI KeySXKFYDWIBCRCRI-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
  • Isoflavanone
  • Isoflavan
  • Furanochromone
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Tertiary alcohol
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point282 - 283 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.27ALOGPS
logP1.97ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.04ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area87.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity92.91 m³·mol⁻¹ChemAxon
Polarizability36.96 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ap0-4957000000-b5e0e752cac2bc9cc495Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0hb9-9552600000-2c8a1bda77820e1105a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-2fef031c1b6351ce04a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02t9-0529000000-380c1285be3e36cffd8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0900000000-293b8bb54048daec58c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-c02bcb402d574c02ac18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0219000000-2e8a29ca74752487d58cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1902000000-03a676e8b6424178be53Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FooDB IDFDB012416
KNApSAcK IDC00009584
Chemspider ID24842947
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257408
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .