Showing Compound Card for Chalconaringenin (CDB005180)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:17:23 UTC
Updated at2020-11-18 16:39:28 UTC
CannabisDB IDCDB005180
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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). Chalconaringenin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2',4',6',4-TetrahydroxychalconeChEBI
2'4'6'4-TetrahydroxychalconeChEBI
IsosalipurpolChEBI
Naringenin chalconeChEBI
2',4,4',6'-TetrahydroxychalconeKegg
Naringenin chalcone, (e)-isomerMeSH
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one, 9ciHMDB
Chemical FormulaC15H12O5
Average Molecular Weight272.25
Monoisotopic Molecular Weight272.0685
IUPAC Name(2E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
Traditional Namenaringenin chalcone
CAS Registry Number5071-40-9
SMILES
OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2O)C=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point184 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
Sulfotransferase 1A3SULT1A3P0DMM9 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029631
DrugBank IDNot Available
Phenol Explorer Compound ID106
FoodDB IDFDB000801
KNApSAcK IDC00007233
Chemspider ID4444447
KEGG Compound IDC06561
BioCyc IDCPD-20012
BiGG IDNot Available
Wikipedia LinkNaringenin chalcone
METLIN IDNot Available
PubChem Compound5280960
PDB IDNot Available
ChEBI ID15413
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Enzyme Details
2. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96