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Chalconaringenin (FDB000801)

Record Information
Version1.0
Creation date2010-04-08 22:04:43 UTC
Update date2020-09-17 15:40:55 UTC
Primary IDFDB000801
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChalconaringenin
DescriptionChalconaringenin, also known as isosalipurpol or naringenin chalcone, belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, chalconaringenin is considered to be a flavonoid lipid molecule. Naringenin chalcone can spontaneously cyclize to naringenin (a flavanone). Chalconaringenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Chalconaringenin has been detected, but not quantified in, several different foods, such as canola, grapefruit/pummelo hybrids, yellow wax beans, horseradish tree, and wild carrots. This could make chalconaringenin a potential biomarker for the consumption of these foods. In plant cells, this process is catalyzed by chalcone isomerase. It is synthesized from 4-coumaroyl-CoA and malonyl-CoA by chalcone synthase (CHS), a key enzyme in the phenylpropanoid pathway. Naringenin chalcone is a common chalconoid (or chalcone, not to be confused with the compound chalcone).
CAS Number5071-40-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.076 g/LALOGPS
logP2.66ALOGPS
logP3.98ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.99ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.8 m³·mol⁻¹ChemAxon
Polarizability27.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H12O5
IUPAC name(2E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
InChI IdentifierInChI=1S/C15H12O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-8,16-17,19-20H/b6-3+
InChI KeyYQHMWTPYORBCMF-ZZXKWVIFSA-N
Isomeric SMILESOC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2O)C=C1
Average Molecular Weight272.2528
Monoisotopic Molecular Weight272.068473494
Classification
Description Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent2'-Hydroxychalcones
Alternative Parents
Substituents
  • 2'-hydroxychalcone
  • Cinnamylphenol
  • Hydroxycinnamic acid or derivatives
  • Acylphloroglucinol derivative
  • Benzenetriol
  • Phloroglucinol derivative
  • Benzoyl
  • Aryl ketone
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Acryloyl-group
  • Vinylogous acid
  • Enone
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.17%; H 4.44%; O 29.38%DFC
Melting PointMp 184° (173-174°)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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSChalconaringenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-1960000000-9097b1de0c14d45c5542Spectrum
Predicted GC-MSChalconaringenin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-1001490000-e95c55e7dac061c94089Spectrum
Predicted GC-MSChalconaringenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSChalconaringenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0910000000-28987f355a39728ed8e42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0190000000-f40a3d639173b6ae573e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0910000000-afe3bb20e731810500522017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-2900000000-37be5bc5a9f1bc38d3022017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-7900000000-42ef7b65ce430e844b492017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-f174e512861692b4e2632017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udj-0920000000-1bfd55f600a901a79c872017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-79afec38b3dde07593f32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gbc-9700000000-ed15b50aa1d66f06bf422017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0910000000-28987f355a39728ed8e42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Positivesplash10-0udj-0920000000-1bfd55f600a901a79c872021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-00di-0090000000-f174e512861692b4e2632021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-73a5344932a9ca8351f82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0gbc-9800000000-91db3ba3ab52b818bda82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Negativesplash10-014i-7900000000-42ef7b65ce430e844b492021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-37be5bc5a9f1bc38d3022021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-00di-0190000000-f40a3d639173b6ae573e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Negativesplash10-0udi-0910000000-7ac383936fce20bb627c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-00di-0190000000-937a14a3c560723f4aba2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-a136c12a30ff8100fd0f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmj-0970000000-c891c7a89172d11fb3842016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy0-2900000000-ceae18eec98b8371efce2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0390000000-ba4a03caa04723dce75e2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0930000000-e887b684ab63fe1aa31b2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-2910000000-5da59f378593488644082016-08-04View Spectrum
NMRNot Available
ChemSpider ID4444447
ChEMBL IDCHEMBL338066
KEGG Compound IDC06561
Pubchem Compound ID5280960
Pubchem Substance IDNot Available
ChEBI ID15413
Phenol-Explorer ID106
DrugBank IDNot Available
HMDB IDHMDB29631
CRC / DFC (Dictionary of Food Compounds) IDBHR20-S:BHR20-S
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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
anti allergic50857 A drug used to treat allergic reactions.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference