Showing Compound Card for Liquiritigenin (CDB005187)

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Record Information
Version1.0
Created at2020-04-17 19:18:05 UTC
Updated at2020-11-18 16:39:29 UTC
CannabisDB IDCDB005187
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameLiquiritigenin
DescriptionLiquiritigenin, also known as 5-deoxyflavanone or DFV, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, liquiritigenin is considered to be a flavonoid lipid molecule. Liquiritigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Liquiritigenin is a bitter tasting compound. Outside of the human body, Liquiritigenin has been detected, but not quantified in, several different foods, such as turnips, kelps, chinese mustards, medlars, and lettuces. This could make liquiritigenin a potential biomarker for the consumption of these foods. Liquiritigenin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-LiquiritigeninChEBI
(2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-oneChEBI
(2S)-LiquiritigeninChEBI
4',7-DihydroxyflavanoneChEBI
7,4'-DihydroxyflavanoneChEBI
(-)-(2S)-7,4'-DihydroxyflavanoneHMDB
(-)-(2S)-7,4’-DihydroxyflavanoneHMDB
(-)-(S)-4',7-DihydroxyflavanoneHMDB
(-)-(S)-4’,7-DihydroxyflavanoneHMDB
(2S)-2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneHMDB
(2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-oneHMDB
4’,7-DihydroxyflavanoneHMDB
7,4’-DihydroxyflavanoneHMDB
LiquiritigeninHMDB
5-DeoxyflavanoneHMDB
DFVHMDB
Chemical FormulaC15H12O4
Average Molecular Weight256.25
Monoisotopic Molecular Weight256.0736
IUPAC Name(2S)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5-deoxyflavanone
CAS Registry Number578-86-9
SMILES
OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2
InChI Identifier
InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1
InChI KeyFURUXTVZLHCCNA-AWEZNQCLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanones
Alternative Parents
Substituents
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavanone
  • Chromone
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point203 - 205 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.79ALOGPS
logP2.49ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.79ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.31 m³·mol⁻¹ChemAxon
Polarizability26.41 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLiquiritigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06vr-1290000000-473372a9cbd8aa299c8cSpectrum
Predicted GC-MSLiquiritigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0900000000-8829ca13726fa5ef28942017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0090010000-4f0e0e7c69cd0563f1542017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014r-0900000000-8829ca13726fa5ef28942017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - QIT 4V, positivesplash10-0a4i-0090000000-e0ef2b922828538142d62020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QIT 15V, positivesplash10-01pa-0990000000-b55ccc74a2ff9f8ee58a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4r-0690000000-e4eb8456793483d7e47b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000i-0910000000-1b26412c239d13150a162020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQQ , positivesplash10-0a4i-0090000000-5a6df4ef73b17801c15b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 17V, positivesplash10-0a4r-0390000000-030c074282d57f882ea62020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 17V, positivesplash10-000j-0970000000-cc482ab502fe16da0b2c2020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014r-0900000000-8829ca13726fa5ef28942021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-7e114a20c600b4c232182021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-00ac566b03c0d20a16bc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014r-0900000000-37f3374e06351b5926242021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-0910000000-afbe3e4c5fceeb057aac2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-1900000000-541af142929c530ffba12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ap0-0970000000-5d4e47f2631f47124cc42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-93474b44c5d1cb8cb1552017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0790000000-572e47bb5dd6e39a50832017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rj-5910000000-47c758a4f16f999867aa2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-b48d7117a74eb8dea54d2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0290000000-24d9ef16fb94c78f6cd92017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-6930000000-82d8508c6ca9b5e8be2a2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-74e7833e04a924835b1e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0790000000-f21efeafedd047dfaebd2021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029519
DrugBank IDDB03601
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000655
KNApSAcK IDC00000977
Chemspider ID102790
KEGG Compound IDC09762
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLiquiritigenin
METLIN IDNot Available
PubChem Compound114829
PDB IDNot Available
ChEBI ID28777
References
General ReferencesNot Available