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Showing Compound Liquiritigenin (FDB000655)

Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2025-11-18 22:20:46 UTC
Primary IDFDB000655
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 nuts, winged beans (Psophocarpus tetragonolobus), brussel sprouts (Brassica oleracea var. gemmifera), green vegetables, and prairie turnips (Pediomelum esculentum). This could make liquiritigenin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Liquiritigenin.
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
LiquiritigeninHMDB
5-DeoxyflavanoneHMDB
DFVHMDB
(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
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
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06vr-1290000000-473372a9cbd8aa299c8cSpectrum
Predicted GC-MS, 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
ChemSpider ID1818
ChEMBL IDCHEMBL252642
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 An agent that regulates mood, reducing symptoms of depression and anxiety by altering neurotransmitter levels in the brain, commonly used in managing depression, anxiety disorders, and other mood disorders.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Anti ulcer49201 An agent that reduces stomach acid and protects the mucous lining, preventing ulcer formation. It is used to treat conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome, promoting healing and relieving symptoms.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Central nervous system active35470 An agent that affects brain and spinal cord function, influencing mood, cognition, and physical responses. Therapeutically, it's used to manage neurological and psychiatric disorders, such as depression, anxiety, and insomnia, by modulating neurotransmitter activity and neural pathways.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Hemoglobin inducerAn agent that stimulates production of hemoglobin, playing a crucial role in treating anemia and other blood disorders by increasing red blood cell count and oxygen delivery to tissues.DUKE
Monoamine-oxidase inhibitor23924 An agent that blocks monoamine oxidase enzymes, increasing neurotransmitter levels. Therapeutically, it reduces depression symptoms and is commonly used in managing depression, anxiety disorders, and Parkinson's disease.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Phytoalexin26115 A plant-derived compound that plays a biological role in defense against pathogens. It has therapeutic applications as an antimicrobial, antioxidant, and anti-inflammatory agent, with key medical uses in managing infections, cancer, and neurodegenerative diseases.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.