You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:33:16 UTC
Update Date2019-07-23 06:23:30 UTC
HMDB IDHMDB0037316
Secondary Accession Numbers
  • HMDB37316
Metabolite Identification
Common NameIsoliquiritigenin
DescriptionIsoliquiritigenin, also known as 6'-deoxychalcone or GU 17, 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, isoliquiritigenin is considered to be a flavonoid lipid molecule. Isoliquiritigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Isoliquiritigenin is a bitter tasting compound. Outside of the human body, Isoliquiritigenin has been detected, but not quantified in, several different foods, such as oval-leaf huckleberries, elliott's blueberries, nanking cherries, common salsifies, and mugworts. This could make isoliquiritigenin a potential biomarker for the consumption of these foods. It can target miR-301b/LRIG1 signaling pathways, resulting in the inhibition of melanoma growth in vitro. The enzyme 6'-deoxychalcone synthase uses malonyl-CoA, 4-coumaroyl-CoA, NADPH, and H+ to produce CoA, isoliquiritigenin, CO2, NADP+, and H2O.The enzyme isoliquiritigenin 2'-O-methyltransferase further transforms isoliquiritigenin into 2'-O-methylisoliquiritigenin. Isoliquiritigenin is a phenolic chemical compound found in licorice. Isoliquiritigenin has been found to be a potent (65 times higher affinity than diazepam) GABA-A benzodiapine receptor positive allosteric modulator.
Structure
Data?1563863010
Synonyms
ValueSource
(e)-1-(2,4-Dihydroxy-phenyl)-3-(4-hydroxy-phenyl)-propenoneChEBI
(e)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propene-1-oneChEBI
2',4,4'-TrihydroxychalconeChEBI
4,2',4'-TrihydroxychalconeChEBI
trans-2',4,4'-TrihydroxychalconeChEBI
1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-oneHMDB
1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-oneHMDB
2',4',4-TrihydroxychalconeHMDB
2',4'-Dihydroxy-3-(p-hydroxyphenyl)-acrylophenoneHMDB
2',4,4'-Trihydroxy-chalconeHMDB
42'4'-TrihydroxychalconeHMDB
6'-DeoxychalconeHMDB
GU 17HMDB
GU-17HMDB
Chemical FormulaC15H12O4
Average Molecular Weight256.2534
Monoisotopic Molecular Weight256.073558872
IUPAC Name(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Traditional Nameisoliquiritigenin
CAS Registry Number961-29-5
SMILES
OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2)C=C1
InChI Identifier
InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+
InChI KeyDXDRHHKMWQZJHT-FPYGCLRLSA-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
  • Benzoyl
  • Resorcinol
  • Styrene
  • Aryl ketone
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point200 - 204 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.055 g/LALOGPS
logP3.04ALOGPS
logP3.63ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.11ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.82 m³·mol⁻¹ChemAxon
Polarizability26.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1970000000-6164f65f5d6241a006f8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-1034900000-76ae3aa74bffdff7ee01Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0000009000-afd1640b539ec58a4616Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0000009000-afd1640b539ec58a4616Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0900000000-e7c4095e90f57884e80cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0090000000-788e4464b6a542aa7c22Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTOF , Positivesplash10-000i-0910000000-15db3efa5c81e3e8fc3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014r-0900000000-e7c4095e90f57884e80cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0910000000-15db3efa5c81e3e8fc3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-1930000000-6d143294fc9a6a343052Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 17V, positivesplash10-000j-0490000000-5d95d877601bf1780cf7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 17V, positivesplash10-000j-0970000000-6f6553743b88b6c220e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-810f1a7ccbea17d944d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052s-0960000000-9529b79414d923c90873Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ks-4910000000-f074bc6f0bf8212cf9ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0290000000-a373dc716189e73d742cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0690000000-12c68dfca23fb3e6405dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-5910000000-ecfe8b4bdcef6eaa160eSpectrum
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 IDDB03285
Phenol Explorer Compound IDNot Available
FooDB IDFDB016335
KNApSAcK IDC00006925
Chemspider ID553829
KEGG Compound IDC08650
BioCyc IDCPD-3041
BiGG IDNot Available
Wikipedia LinkIsoliquiritigenin
METLIN IDNot Available
PubChem Compound638278
PDB IDHCC
ChEBI ID310312
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. de Barros Machado T, Leal IC, Kuster RM, Amaral AC, Kokis V, de Silva MG, dos Santos KR: Brazilian phytopharmaceuticals--evaluation against hospital bacteria. Phytother Res. 2005 Jun;19(6):519-25. [PubMed:16114081 ]
  2. Tawata M, Aida K, Noguchi T, Ozaki Y, Kume S, Sasaki H, Chin M, Onaya T: Anti-platelet action of isoliquiritigenin, an aldose reductase inhibitor in licorice. Eur J Pharmacol. 1992 Feb 25;212(1):87-92. [PubMed:1555643 ]
  3. Gaur R, Kumar S, Trivedi P, Bhakuni RS, Bawankule DU, Pal A, Shanker K: Liquiritigenin derivatives and their hepatotoprotective activity. Nat Prod Commun. 2010 Aug;5(8):1243-6. [PubMed:20839627 ]
  4. Park I, Park KK, Park JH, Chung WY: Isoliquiritigenin induces G2 and M phase arrest by inducing DNA damage and by inhibiting the metaphase/anaphase transition. Cancer Lett. 2009 May 18;277(2):174-81. doi: 10.1016/j.canlet.2008.12.005. Epub 2009 Jan 23. [PubMed:19167809 ]
  5. Yu SM, Kuo SC: Vasorelaxant effect of isoliquiritigenin, a novel soluble guanylate cyclase activator, in rat aorta. Br J Pharmacol. 1995 Apr;114(8):1587-94. [PubMed:7599926 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .