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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:48:53 UTC
Update Date2019-07-23 06:14:59 UTC
HMDB IDHMDB0034039
Secondary Accession Numbers
  • HMDB34039
Metabolite Identification
Common NameDolineone
DescriptionDolineone, also known as dolichone, 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, dolineone is considered to be a flavonoid lipid molecule. Dolineone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Dolineone has been detected, but not quantified in, jicama and pulses. This could make dolineone a potential biomarker for the consumption of these foods.
Structure
Data?1563862499
Synonyms
ValueSource
(+)-DolineoneHMDB
6a,13a-Dihydro-1,3-dioxolo[6,7][1]benzopyrano[3,4-b]furo[3,2-g][1]benzopyran-13(6H)-one, 9ciHMDB
DolichoneHMDB
Chemical FormulaC19H12O6
Average Molecular Weight336.295
Monoisotopic Molecular Weight336.063388116
IUPAC Name5,7,11,14,18-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
Traditional Namedolineone
CAS Registry Number10065-28-8
SMILES
O=C1C2C(COC3=CC4=C(OCO4)C=C23)OC2=C1C=C1C=COC1=C2
InChI Identifier
InChI=1S/C19H12O6/c20-19-11-3-9-1-2-21-12(9)5-14(11)25-17-7-22-13-6-16-15(23-8-24-16)4-10(13)18(17)19/h1-6,17-18H,7-8H2
InChI KeyRAJDDCCSNZAPCH-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
  • Benzodioxole
  • Benzofuran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Ketone
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point233 - 235 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP3.07ALOGPS
logP2.5ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)10.43ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area67.13 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.51 m³·mol⁻¹ChemAxon
Polarizability33.57 ųChemAxon
Number of Rings6ChemAxon
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, Positivesplash10-0a4l-2819000000-edb336889e511cfef035Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-8b33061978fbf6a44600Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0329000000-bf271617ade8e362283bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0921000000-be65b7425e7f76a39b64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-2557d6ca9a6e4c5b8bfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0019000000-964f57b779ee0766ead5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-0911000000-33c608b6d67401bdab98Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB012281
KNApSAcK IDC00009568
Chemspider ID4475907
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5316959
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.. .