Record Information
Version1.0
Creation date2010-04-08 22:10:10 UTC
Update date2019-11-26 03:06:45 UTC
Primary IDFDB012432
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). Cernuine has been detected, but not quantified in, citrus and lemons. This could make cernuine a potential biomarker for the consumption of these foods.
CAS Number480-70-6
Structure
Thumb
Synonyms
SynonymSource
4,6-Dihydroxy-2-[(3,4-dihydroxyphenyl)methylene]-3(2H)-benzofuranone, 9ciHMDB
AureusidinHMDB
4,6-Dihydroxy-2-[(3,4-dihydroxyphenyl)methylene]-3(2H)-benzofuranone, 9CIdb_source
Cernuinedb_source
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H10O6
IUPAC name(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-2,3-dihydro-1-benzofuran-3-one
InChI IdentifierInChI=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
Isomeric SMILESOC1=CC(O)=C2C(=O)\C(OC2=C1)=C/C1=CC(O)=C(O)C=C1
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.94%; H 3.52%; O 33.54%DFC
Melting PointMp 295 dec. (double Mp)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abi-0590000000-60fdd1319931a92de30eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0nt9-3340190000-3606f26744a113b986b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-3224cb2e84a595e2b340JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0890000000-c05de1376c18f593bf58JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9i-3910000000-e8808b7a3e9006b5469cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-fdb1d3719d99503795dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-610762391e234975806cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-4980000000-43383fa8b2882e1be447JSpectraViewer
ChemSpider ID11284214
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6123196
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34150
CRC / DFC (Dictionary of Food Compounds) IDHGW26-E:HGW26-E
EAFUS IDNot Available
Dr. Duke IDAUREUSIDIN
BIGG IDNot Available
KNApSAcK IDC00008027
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
iodothyronine-deiodinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pigment26130 An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).