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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:53:40 UTC
Update Date2018-03-12 21:58:37 UTC
HMDB IDHMDB0034960
Secondary Accession Numbers
  • HMDB34960
Metabolite Identification
Common NameEdulone A
DescriptionEdulone a belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Edulone a exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, edulone a is primarily located in the membrane (predicted from logP). Outside of the human body, edulone a can be found in root vegetables. This makes edulone a a potential biomarker for the consumption of this food product.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H22O8
Average Molecular Weight414.4053
Monoisotopic Molecular Weight414.13146768
IUPAC Name2-{3,4,6-trihydroxy-1,12-dimethyl-8,11-dioxo-10-oxatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-2(7),3,5,9(16),12-pentaen-5-yl}propyl acetate
Traditional Name2-{3,4,6-trihydroxy-1,12-dimethyl-8,11-dioxo-10-oxatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-2(7),3,5,9(16),12-pentaen-5-yl}propyl acetate
CAS Registry Number68421-12-5
SMILES
CC(COC(C)=O)C1=C(O)C2=C(C(O)=C1O)C1(C)CCC3=C(C)C(=O)OC(=C13)C2=O
InChI Identifier
InChI=1S/C22H22O8/c1-8(7-29-10(3)23)12-16(24)13-15(19(27)17(12)25)22(4)6-5-11-9(2)21(28)30-20(14(11)22)18(13)26/h8,24-25,27H,5-7H2,1-4H3
InChI KeyMLTCCXPBXYMUMQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNaphthopyranones
Direct ParentNaphthopyranones
Alternative Parents
Substituents
  • Naphthopyranone
  • Naphthalene
  • Aryl ketone
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Polyol
  • Oxacycle
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point153 - 159 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.057 g/LALOGPS
logP2.67ALOGPS
logP2.81ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.62ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area130.36 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.14 m³·mol⁻¹ChemAxon
Polarizability41.99 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4309000000-4277e29849e83d4ae962View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-4110069000-36b937fdf4881724df66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066r-0109500000-ef6f1fa669050360a6a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2209000000-7f4db93aa75e4e143051View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2249000000-d82e1f73b55757d8dd82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-5006900000-c87aff0f61869a5b5241View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-9017200000-2e19826287799d7fb356View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-cc6cbafc484fe192bfccView in MoNA
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
FoodDB IDFDB013555
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI 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.. .