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Showing Compound Liquiritigenin (FDB000655)

Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2019-11-26 02:55:09 UTC
Primary IDFDB000655
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. Liquiritigenin has been detected, but not quantified in, several different foods, such as peach (var.), rowanberries, common cabbages, common hazelnuts, and oyster mushrooms. This could make liquiritigenin a potential biomarker for the consumption of these foods.
CAS Number578-86-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-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
5-DeoxyflavanoneHMDB
DFVHMDB
LiquiritigeninHMDB
(S)-4',7-Dihydroxyflavanonemanual
2S,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-onemanual
5-DEOXYFLAVANONEHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
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
Chemical FormulaC15H12O4
IUPAC name(2S)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=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
InChI KeyFURUXTVZLHCCNA-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(C=C1)C1CC(=O)C2=C(O1)C=C(O)C=C2
Average Molecular Weight256.257
Monoisotopic Molecular Weight256.073558866
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.31%; H 4.72%; O 24.97%DFC
Melting PointMp 203-205°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -36.2 (c, 0.09 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0729-1390000000-28ed6632799d2db10d20Spectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312abSpectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb6Spectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06vr-1290000000-473372a9cbd8aa299c8cSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0900000000-8829ca13726fa5ef2894Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0090010000-4f0e0e7c69cd0563f154Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014r-0900000000-8829ca13726fa5ef2894Spectrum
MS/MSLC-MS/MS Spectrum - QIT 4V, positivesplash10-0a4i-0090000000-e0ef2b922828538142d6Spectrum
MS/MSLC-MS/MS Spectrum - QIT 15V, positivesplash10-01pa-0990000000-b55ccc74a2ff9f8ee58aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4r-0690000000-e4eb8456793483d7e47bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000i-0910000000-1b26412c239d13150a16Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQQ , positivesplash10-0a4i-0090000000-5a6df4ef73b17801c15bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 17V, positivesplash10-0a4r-0390000000-030c074282d57f882ea6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 17V, positivesplash10-000j-0970000000-cc482ab502fe16da0b2cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-93474b44c5d1cb8cb155Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0790000000-572e47bb5dd6e39a5083Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rj-5910000000-47c758a4f16f999867aaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-b48d7117a74eb8dea54dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0290000000-24d9ef16fb94c78f6cd9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-6930000000-82d8508c6ca9b5e8be2aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-74e7833e04a924835b1eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0790000000-f21efeafedd047dfaebdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-dbd38546a036e6ece955Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-95fde3556f3ac1e6ef94Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052s-0940000000-0080393a0c361f79939dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-3eb17350877e96e50caaSpectrum
NMR
TypeDescriptionView
ChemSpider ID1818
ChEMBL IDNot Available
KEGG Compound IDC09762
Pubchem Compound ID1889
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB03601
HMDB IDHMDB29519
CRC / DFC (Dictionary of Food Compounds) IDBFK34-C:BFK72-M
EAFUS IDNot Available
Dr. Duke IDLIQUIRITIGENIN
BIGG IDNot Available
KNApSAcK IDC00000977
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLiquiritigenin
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 depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
central nervous system active35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hemoglobin inducerDUKE
monoamine-oxidase 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
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.