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Showing Compound Isoliquiritigenin (FDB016335)

Record Information
Version1.0
Creation date2010-04-08 22:12:22 UTC
Update date2020-09-17 15:40:58 UTC
Primary IDFDB016335
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number961-29-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
2',4',4-trihydroxychalconebiospider
42'4'-trihydroxychalconebiospider
6'-deoxychalconebiospider
Acrylophenone, 2',4'-dihydroxy-3-(p-hydroxyphenyl)-biospider
Chalcone, 2',4,4'-trihydroxy-biospider
Isoliquiritigenindb_source
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
Chemical FormulaC15H12O4
IUPAC name(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
InChI IdentifierInChI=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
Isomeric SMILESOC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2)C=C1
Average Molecular Weight256.2534
Monoisotopic Molecular Weight256.073558872
Classification
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:

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 200-204° (198-200°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[base] lmax 428 () (MeOH-NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
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
ChemSpider ID553829
ChEMBL IDCHEMBL129795
KEGG Compound IDC08650
Pubchem Compound ID638278
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID918
DrugBank IDDB03285
HMDB IDHMDB37316
CRC / DFC (Dictionary of Food Compounds) IDKQQ39-F:KQQ39-F
EAFUS IDNot Available
Dr. Duke IDISOLIQUIRITIGENIN
BIGG IDNot Available
KNApSAcK IDC00006925
HET IDHCC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID918
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti aggregantDUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ischemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti platelet aggregation factor50427 A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.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
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
estrogenicDUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
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
myorelaxantDUKE
peroxidase 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
pigment26130 An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.DUKE
quinone-reductase 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
tyrosine-kinase 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
vasorelaxantDUKE
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.