Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:04:57 UTC
Update Date2022-03-07 02:54:02 UTC
HMDB IDHMDB0034278
Secondary Accession Numbers
  • HMDB34278
Metabolite Identification
Common NameAuranetin
DescriptionAuranetin belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, auranetin is considered to be a flavonoid. Auranetin has been detected, but not quantified in, citrus. This could make auranetin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Auranetin.
Structure
Data?1563862538
Synonyms
ValueSource
3,4',6,7,8-PentamethoxyflavoneHMDB
AurantinMeSH, HMDB
Chemical FormulaC20H20O7
Average Molecular Weight372.3686
Monoisotopic Molecular Weight372.120902994
IUPAC Name3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Nameauranetin
CAS Registry Number522-16-7
SMILES
COC1=CC=C(C=C1)C1=C(OC)C(=O)C2=CC(OC)=C(OC)C(OC)=C2O1
InChI Identifier
InChI=1S/C20H20O7/c1-22-12-8-6-11(7-9-12)16-19(25-4)15(21)13-10-14(23-2)18(24-3)20(26-5)17(13)27-16/h6-10H,1-5H3
InChI KeyDGNOHOXRWCCDLK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent8-O-methylated flavonoids
Alternative Parents
Substituents
  • 3-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • Flavone
  • 3-methoxychromone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Phenol ether
  • Pyranone
  • Alkyl aryl ether
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Point141 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility41.15 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP2.84ALOGPS
logP2.2ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area72.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.54 m³·mol⁻¹ChemAxon
Polarizability38.76 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.10531661259
DarkChem[M-H]-187.70631661259
DeepCCS[M+H]+185.47130932474
DeepCCS[M-H]-183.11430932474
DeepCCS[M-2H]-217.02530932474
DeepCCS[M+Na]+192.25330932474
AllCCS[M+H]+187.632859911
AllCCS[M+H-H2O]+184.532859911
AllCCS[M+NH4]+190.532859911
AllCCS[M+Na]+191.332859911
AllCCS[M-H]-191.432859911
AllCCS[M+Na-2H]-191.332859911
AllCCS[M+HCOO]-191.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AuranetinCOC1=CC=C(C=C1)C1=C(OC)C(=O)C2=CC(OC)=C(OC)C(OC)=C2O14418.3Standard polar33892256
AuranetinCOC1=CC=C(C=C1)C1=C(OC)C(=O)C2=CC(OC)=C(OC)C(OC)=C2O13157.0Standard non polar33892256
AuranetinCOC1=CC=C(C=C1)C1=C(OC)C(=O)C2=CC(OC)=C(OC)C(OC)=C2O13142.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Auranetin GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-0219000000-9ee686399a197fc968512017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Auranetin 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 - Auranetin 10V, Positive-QTOFsplash10-00di-0009000000-0ecb060eaa87b3d213cf2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auranetin 20V, Positive-QTOFsplash10-00di-0009000000-27aa543cff13cc47b7d62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auranetin 40V, Positive-QTOFsplash10-03fu-0459000000-b6bdd6425964d501daca2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auranetin 10V, Negative-QTOFsplash10-00di-0009000000-55bf8209b4a4b235f6ac2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auranetin 20V, Negative-QTOFsplash10-00di-0009000000-20f0f0f1a0ecb19b36ce2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auranetin 40V, Negative-QTOFsplash10-0a4i-2490000000-b059ea4686056ef866282015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auranetin 10V, Negative-QTOFsplash10-00di-0009000000-c528cfb3e87592b0a62b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auranetin 20V, Negative-QTOFsplash10-00di-0029000000-2382023a76e302e4447a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auranetin 40V, Negative-QTOFsplash10-0ab9-1922000000-53a082c423c2b403768a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auranetin 10V, Positive-QTOFsplash10-00di-0009000000-aa9385dbb205bb238b882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auranetin 20V, Positive-QTOFsplash10-00di-0009000000-9877ae6f6844dab4ca762021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Auranetin 40V, Positive-QTOFsplash10-03k9-2195000000-30e47aeb9d466c8689a52021-09-24Wishart 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 IDFDB012615
KNApSAcK IDC00004657
Chemspider ID10196
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10643
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1841631
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.. .