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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:29:41 UTC
Update Date2019-07-23 06:14:12 UTC
HMDB IDHMDB0033735
Secondary Accession Numbers
  • HMDB33735
Metabolite Identification
Common NameGraveolone
DescriptionGraveolone belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Graveolone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Graveolone has been detected, but not quantified in, a few different foods, such as dills, herbs and spices, and parsley. This could make graveolone a potential biomarker for the consumption of these foods.
Structure
Data?1563862452
Synonyms
ValueSource
6,7-Dihydro-8,8-dimethyl-2H,8H-benzo-(1,2b:5,4')-dipyran-2,6-dioneHMDB
6,7-Dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2,6-dioneHMDB
8,8-Dimethyl-7,8-dihydro-pyrano[3,2-g]chromene-2,6-dioneHMDB
Chemical FormulaC14H12O4
Average Molecular Weight244.2427
Monoisotopic Molecular Weight244.073558872
IUPAC Name13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),6,9-tetraene-5,11-dione
Traditional Name13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0³,⁸]tetradeca-1,3(8),6,9-tetraene-5,11-dione
CAS Registry Number16499-05-1
SMILES
CC1(C)CC(=O)C2=CC3=C(OC(=O)C=C3)C=C2O1
InChI Identifier
InChI=1S/C14H12O4/c1-14(2)7-10(15)9-5-8-3-4-13(16)17-11(8)6-12(9)18-14/h3-6H,7H2,1-2H3
InChI KeyWEDGVCZUPFZNDE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassPyranocoumarins
Direct ParentLinear pyranocoumarins
Alternative Parents
Substituents
  • Linear pyranocoumarin
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Ketone
  • Lactone
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point177.5 - 178 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.082 g/LALOGPS
logP2.37ALOGPS
logP1.82ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)15.01ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.61 m³·mol⁻¹ChemAxon
Polarizability24.87 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-0v04-1490000000-7a6369d0bc5de809c822Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-f8c8fdb3c697796b2901Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-2490000000-0a2c1ec23384a04b14d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052s-5900000000-c5eda937cca4cc3ed621Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-99d4fe5456bf67dcebe3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0490000000-8381a207dd70772c1cfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-4910000000-a9e396f685ac07b07483Spectrum
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 IDFDB011859
KNApSAcK IDNot Available
Chemspider ID154741
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound177751
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.. .
  2. (). Ashok S. Mujumdar and Ramesh N. Usgaonkar, “Benzodipyrans. Part V. Synthesis of a linear dihydrobenzodipyrandione isolated from dill and of other similar benzodipyrandiones,” Journal of the Chemical Society, Perkin Transactions 1 (1974): 2236-2239. [Structure]. .