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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:12:46 UTC
Update Date2022-03-07 02:53:43 UTC
HMDB IDHMDB0033480
Secondary Accession Numbers
  • HMDB33480
Metabolite Identification
Common NameGraveoline
DescriptionGraveoline belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Graveoline has been detected, but not quantified in, herbs and spices. This could make graveoline a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Graveoline.
Structure
Data?1563862412
Synonyms
ValueSource
1-Methyl-2-(3,4-methylenedioxyphenyl)-4(1H)-quinolinoneHMDB
2-(1,3-Benzodioxol-5-yl)-1-methyl-4(1H)-quinolinone, 9ciHMDB
Alkaloid from ruta angustifolia plantHMDB
FoliosineHMDB
GraveolinHMDB
RutamineHMDB
Chemical FormulaC17H13NO3
Average Molecular Weight279.29
Monoisotopic Molecular Weight279.089543287
IUPAC Name2-(2H-1,3-benzodioxol-5-yl)-1-methyl-1,4-dihydroquinolin-4-one
Traditional Namegraveoline
CAS Registry Number485-61-0
SMILES
CN1C2=CC=CC=C2C(=O)C=C1C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C17H13NO3/c1-18-13-5-3-2-4-12(13)15(19)9-14(18)11-6-7-16-17(8-11)21-10-20-16/h2-9H,10H2,1H3
InChI KeyCOBBNRKBTCBWQP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinolones and derivatives
Direct ParentHydroquinolones
Alternative Parents
Substituents
  • Dihydroquinolone
  • Dihydroquinoline
  • Benzodioxole
  • Pyridine
  • Benzenoid
  • Vinylogous amide
  • Heteroaromatic compound
  • Azacycle
  • Acetal
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen 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 Point205 - 205.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP2.6ALOGPS
logP2.71ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)16.75ChemAxon
pKa (Strongest Basic)2.04ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity80.7 m³·mol⁻¹ChemAxon
Polarizability29.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.00631661259
DarkChem[M-H]-164.78531661259
DeepCCS[M+H]+160.55630932474
DeepCCS[M-H]-158.19830932474
DeepCCS[M-2H]-191.08430932474
DeepCCS[M+Na]+166.64930932474
AllCCS[M+H]+163.932859911
AllCCS[M+H-H2O]+159.932859911
AllCCS[M+NH4]+167.532859911
AllCCS[M+Na]+168.632859911
AllCCS[M-H]-168.432859911
AllCCS[M+Na-2H]-167.432859911
AllCCS[M+HCOO]-166.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GraveolineCN1C2=CC=CC=C2C(=O)C=C1C1=CC2=C(OCO2)C=C13735.0Standard polar33892256
GraveolineCN1C2=CC=CC=C2C(=O)C=C1C1=CC2=C(OCO2)C=C12464.2Standard non polar33892256
GraveolineCN1C2=CC=CC=C2C(=O)C=C1C1=CC2=C(OCO2)C=C13150.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Graveoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufr-0390000000-352611e506ed20b6463f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Graveoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Graveoline , positive-QTOFsplash10-001i-0490000000-d0db66d5f2efb51cb7592017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 10V, Negative-QTOFsplash10-004i-0090000000-d749d0de30e3c73c84e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 20V, Negative-QTOFsplash10-004i-0090000000-65e3894dfa895a4abaf02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 40V, Negative-QTOFsplash10-0ufr-1190000000-30699925815ed3f7bbe82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 10V, Negative-QTOFsplash10-004i-0090000000-8e1bf2c742825f66dfd02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 20V, Negative-QTOFsplash10-004i-0090000000-33097f6056dfc373eda92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 40V, Negative-QTOFsplash10-0f92-0490000000-69166401556d4a9ca8f92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 10V, Positive-QTOFsplash10-001i-0090000000-42928c32f520d5fe63582016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 20V, Positive-QTOFsplash10-001i-0090000000-0c5a9e551562449a223f2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 40V, Positive-QTOFsplash10-0zfr-1290000000-ae55537f5c75c23e21852016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 10V, Positive-QTOFsplash10-001i-0090000000-830673202d5e6529626e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 20V, Positive-QTOFsplash10-001i-0090000000-a6393bc3b8e399fe9d162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Graveoline 40V, Positive-QTOFsplash10-0ue9-0490000000-2384bbc28e0732353f492021-09-23Wishart 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 IDFDB011523
KNApSAcK IDC00002169
Chemspider ID314099
KEGG Compound IDC10689
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound353825
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .