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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:29:41 UTC
Update Date2022-03-07 02:53:50 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 has been detected, but not quantified in, a few different foods, such as dills (Anethum graveolens), herbs and spices, and parsleys (Petroselinum crispum). This could make graveolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Graveolone.
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point177.5 - 178 °CNot Available
Boiling Point439.00 to 440.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility467.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.670 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.90331661259
DarkChem[M-H]-154.38931661259
DeepCCS[M+H]+160.57230932474
DeepCCS[M-H]-158.21430932474
DeepCCS[M-2H]-191.130932474
DeepCCS[M+Na]+166.66530932474
AllCCS[M+H]+152.732859911
AllCCS[M+H-H2O]+148.632859911
AllCCS[M+NH4]+156.532859911
AllCCS[M+Na]+157.632859911
AllCCS[M-H]-158.132859911
AllCCS[M+Na-2H]-157.632859911
AllCCS[M+HCOO]-157.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GraveoloneCC1(C)CC(=O)C2=CC3=C(OC(=O)C=C3)C=C2O13074.0Standard polar33892256
GraveoloneCC1(C)CC(=O)C2=CC3=C(OC(=O)C=C3)C=C2O12219.5Standard non polar33892256
GraveoloneCC1(C)CC(=O)C2=CC3=C(OC(=O)C=C3)C=C2O12210.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Graveolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0v04-1490000000-7a6369d0bc5de809c8222017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Graveolone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Graveolone 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 - Graveolone 10V, Positive-QTOFsplash10-0002-0190000000-f8c8fdb3c697796b29012015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveolone 20V, Positive-QTOFsplash10-000b-2490000000-0a2c1ec23384a04b14d52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveolone 40V, Positive-QTOFsplash10-052s-5900000000-c5eda937cca4cc3ed6212015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveolone 10V, Negative-QTOFsplash10-0006-0190000000-99d4fe5456bf67dcebe32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveolone 20V, Negative-QTOFsplash10-0006-0490000000-8381a207dd70772c1cfc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveolone 40V, Negative-QTOFsplash10-0a4u-4910000000-a9e396f685ac07b074832015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveolone 10V, Positive-QTOFsplash10-0002-0090000000-5665d475819ffb7ca28c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveolone 20V, Positive-QTOFsplash10-0002-0190000000-c4ba5da418678027f39d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveolone 40V, Positive-QTOFsplash10-0a70-2930000000-5dbca00f9547c335e2862021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveolone 10V, Negative-QTOFsplash10-0006-0090000000-c3ceff739ebba19f299c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveolone 20V, Negative-QTOFsplash10-0006-0090000000-9acfa2e26a204df2f25a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveolone 40V, Negative-QTOFsplash10-004i-0790000000-15e9b26d19629b4e09472021-09-25Wishart LabView Spectrum
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 IDC00054134
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
MarkerDB IDNot Available
Good Scents IDrw1583871
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]. .