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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:56:45 UTC
Update Date2019-07-23 06:15:19 UTC
HMDB IDHMDB0034150
Secondary Accession Numbers
  • HMDB34150
Metabolite Identification
Common NameCernuine
DescriptionCernuine, also known as aureusidin, belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus). Cernuine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cernuine has been detected, but not quantified in, citrus and lemons. This could make cernuine a potential biomarker for the consumption of these foods.
Structure
Data?1563862519
Synonyms
ValueSource
4,6-Dihydroxy-2-[(3,4-dihydroxyphenyl)methylene]-3(2H)-benzofuranone, 9ciHMDB
AureusidinHMDB
Chemical FormulaC15H10O6
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
IUPAC Name(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-2,3-dihydro-1-benzofuran-3-one
Traditional Name(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3-one
CAS Registry Number480-70-6
SMILES
OC1=CC(O)=C2C(=O)\C(OC2=C1)=C/C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C15H10O6/c16-8-5-11(19)14-12(6-8)21-13(15(14)20)4-7-1-2-9(17)10(18)3-7/h1-6,16-19H/b13-4+
InChI KeyWBEFUVAYFSOUEA-YIXHJXPBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassAurone flavonoids
Sub ClassNot Available
Direct ParentAurone flavonoids
Alternative Parents
Substituents
  • Aurone
  • Benzofuran
  • Coumaran
  • Catechol
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • 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 Point295 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.68ALOGPS
logP2.64ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.67ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.97 m³·mol⁻¹ChemAxon
Polarizability28.03 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, Positivesplash10-0abi-0590000000-60fdd1319931a92de30eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0nt9-3340190000-3606f26744a113b986b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-3224cb2e84a595e2b340Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0890000000-c05de1376c18f593bf58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9i-3910000000-e8808b7a3e9006b5469cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-fdb1d3719d99503795dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-610762391e234975806cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-4980000000-43383fa8b2882e1be447Spectrum
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 IDFDB012432
KNApSAcK IDC00008027
Chemspider ID11284214
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6123196
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.. .