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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:54 UTC
Update Date2021-09-14 15:47:53 UTC
HMDB IDHMDB0029519
Secondary Accession Numbers
  • HMDB29519
Metabolite Identification
Common NameLiquiritigenin
DescriptionLiquiritigenin 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. Liquiritigenin is a bitter tasting compound. Liquiritigenin has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), kai-lans (Brassica oleracea var. alboglabra), blackberries (Rubus), walnuts (Juglans), and tortilla. This could make liquiritigenin a potential biomarker for the consumption of these foods. Liquiritigenin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Liquiritigenin.
Structure
Data?1582753430
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 Weight256.2534
Monoisotopic Molecular Weight256.073558872
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 Molecular Properties
PropertyValueReference
Melting Point203 - 205 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Liquiritigenin,1TMS,#12677.622https://arxiv.org/abs/1905.12712
Liquiritigenin,1TMS,#22649.873https://arxiv.org/abs/1905.12712
Liquiritigenin,2TMS,#12753.1182https://arxiv.org/abs/1905.12712
Liquiritigenin,1TBDMS,#12952.6782https://arxiv.org/abs/1905.12712
Liquiritigenin,1TBDMS,#22920.4556https://arxiv.org/abs/1905.12712
Liquiritigenin,2TBDMS,#13239.057https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vr-1290000000-473372a9cbd8aa299c8c2017-08-28View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0900000000-8829ca13726fa5ef28942017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0090010000-4f0e0e7c69cd0563f1542017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014r-0900000000-8829ca13726fa5ef28942017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QIT 4V, positivesplash10-0a4i-0090000000-e0ef2b922828538142d62020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QIT 15V, positivesplash10-01pa-0990000000-b55ccc74a2ff9f8ee58a2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4r-0690000000-e4eb8456793483d7e47b2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000i-0910000000-1b26412c239d13150a162020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQQ , positivesplash10-0a4i-0090000000-5a6df4ef73b17801c15b2020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 17V, positivesplash10-0a4r-0390000000-030c074282d57f882ea62020-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 17V, positivesplash10-000j-0970000000-cc482ab502fe16da0b2c2020-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014r-0900000000-8829ca13726fa5ef28942021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-7e114a20c600b4c232182021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-00ac566b03c0d20a16bc2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014r-0900000000-37f3374e06351b5926242021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-0910000000-afbe3e4c5fceeb057aac2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-014i-1900000000-541af142929c530ffba12021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ap0-0970000000-5d4e47f2631f47124cc42021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-93474b44c5d1cb8cb1552017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0790000000-572e47bb5dd6e39a50832017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rj-5910000000-47c758a4f16f999867aa2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-b48d7117a74eb8dea54d2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0290000000-24d9ef16fb94c78f6cd92017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-6930000000-82d8508c6ca9b5e8be2a2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-74e7833e04a924835b1e2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0790000000-f21efeafedd047dfaebd2021-09-22View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03601
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .