Showing Compound Card for Isoliquiritigenin (CDB005186)

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Record Information
Version1.0
Created at2020-04-17 19:17:59 UTC
Updated at2020-12-07 19:11:43 UTC
CannabisDB IDCDB005186
Secondary Accession NumbersNot Available
Cannabis Compound 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 java plums, tea leaf willows, sweet marjorams, common grapes, and black mulberries. This could make isoliquiritigenin a potential biomarker for the consumption of these foods. 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. 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. It can target miR-301b/LRIG1 signaling pathways, resulting in the inhibition of melanoma growth in vitro. Isoliquiritigenin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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, MeSH
2',4'-Dihydroxy-3-(P-hydroxyphenyl)-acrylophenoneHMDB
2',4,4'-Trihydroxy-chalconeHMDB
42'4'-TrihydroxychalconeHMDB
6'-DeoxychalconeHMDB, MeSH
GU 17MeSH, HMDB
GU-17MeSH, HMDB
Chemical FormulaC15H12O4
Average Molecular Weight256.25
Monoisotopic Molecular Weight256.0736
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsoliquiritigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1970000000-6164f65f5d6241a006f8Spectrum
Predicted GC-MSIsoliquiritigenin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-1034900000-76ae3aa74bffdff7ee01Spectrum
Predicted GC-MSIsoliquiritigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsoliquiritigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0000009000-afd1640b539ec58a46162017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0000009000-afd1640b539ec58a46162017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0900000000-e7c4095e90f57884e80c2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0090000000-788e4464b6a542aa7c222017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTOF , Positivesplash10-000i-0910000000-15db3efa5c81e3e8fc3e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014r-0900000000-e7c4095e90f57884e80c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0910000000-15db3efa5c81e3e8fc3e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-1930000000-6d143294fc9a6a3430522017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 17V, positivesplash10-000j-0490000000-5d95d877601bf1780cf72020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 17V, positivesplash10-000j-0970000000-6f6553743b88b6c220e22020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-6646b871effe2fc1dec42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0790000000-a0a66b537f815a68529a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-1900000000-f6d8867bba0f74e95f4c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-001c-7900000000-d9f65201f86e97a923052021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000x-9600000000-4607845a4f3c870a8b7d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-1900000000-5b283194f8e6438d1cb42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014r-0900000000-e7c4095e90f57884e80c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4r-0690000000-7996084c7a5f231793662021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-803b7c0679a83bac81f62021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-810f1a7ccbea17d944d32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052s-0960000000-9529b79414d923c908732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ks-4910000000-f074bc6f0bf8212cf9cc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0290000000-a373dc716189e73d742c2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0690000000-12c68dfca23fb3e6405d2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-5910000000-ecfe8b4bdcef6eaa160e2016-08-04View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0037316
DrugBank IDDB03285
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available