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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:48:53 UTC
Update Date2022-03-07 02:53:57 UTC
HMDB IDHMDB0034039
Secondary Accession Numbers
  • HMDB34039
Metabolite Identification
Common NameDolineone
DescriptionDolineone 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. Dolineone has been detected, but not quantified in, jicamas (Pachyrhizus erosus) and pulses. This could make dolineone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dolineone.
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point233 - 235 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.37531661259
DarkChem[M-H]-175.55731661259
DeepCCS[M-2H]-209.16130932474
DeepCCS[M+Na]+184.38830932474
AllCCS[M+H]+178.732859911
AllCCS[M+H-H2O]+175.332859911
AllCCS[M+NH4]+181.832859911
AllCCS[M+Na]+182.732859911
AllCCS[M-H]-181.732859911
AllCCS[M+Na-2H]-180.532859911
AllCCS[M+HCOO]-179.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DolineoneO=C1C2C(COC3=CC4=C(OCO4)C=C23)OC2=C1C=C1C=COC1=C24690.0Standard polar33892256
DolineoneO=C1C2C(COC3=CC4=C(OCO4)C=C23)OC2=C1C=C1C=COC1=C22937.3Standard non polar33892256
DolineoneO=C1C2C(COC3=CC4=C(OCO4)C=C23)OC2=C1C=C1C=COC1=C23090.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dolineone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-2819000000-edb336889e511cfef0352017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dolineone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dolineone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 10V, Positive-QTOFsplash10-000i-0009000000-8b33061978fbf6a446002016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 20V, Positive-QTOFsplash10-00kr-0329000000-bf271617ade8e362283b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 40V, Positive-QTOFsplash10-03di-0921000000-be65b7425e7f76a39b642016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 10V, Negative-QTOFsplash10-000i-0009000000-2557d6ca9a6e4c5b8bfd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 20V, Negative-QTOFsplash10-000i-0019000000-964f57b779ee0766ead52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 40V, Negative-QTOFsplash10-0a4j-0911000000-33c608b6d67401bdab982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 10V, Positive-QTOFsplash10-000i-0009000000-a487dc1a344a663536352021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 20V, Positive-QTOFsplash10-000i-0009000000-a487dc1a344a663536352021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 40V, Positive-QTOFsplash10-0kbk-0915000000-462d3f76132742d329412021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 10V, Negative-QTOFsplash10-000i-0009000000-cf75db3fcf76086bc0a22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 20V, Negative-QTOFsplash10-000i-0009000000-25a65af29ec4c92f77412021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dolineone 40V, Negative-QTOFsplash10-052r-0209000000-5209610c956607dbb4562021-09-25Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1840001
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.. .