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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 agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Anti-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti-allergic50857 An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.DUKE
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-diabetic52217 An agent that regulates blood sugar levels, enhancing insulin sensitivity or secretion. Therapeutically, it's used to manage diabetes, reducing symptoms and complications, and commonly prescribed to treat type 1 and 2 diabetes, as well as gestational diabetes.DUKE
Anti-ischemic52217 An agent that reduces or prevents tissue damage from inadequate blood flow, commonly used to manage angina, heart attacks, and strokes by improving oxygen delivery and reducing cardiac workload.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti platelet aggregation factor50427 An agent that prevents platelets from clumping, reducing blood clot formation. It plays a biological role in maintaining vascular health, and has therapeutic applications in preventing thrombosis, stroke, and heart attack, with key medical uses in cardiovascular disease management and surgery.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
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.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
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
ApoptoticAn agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy.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
Cyclooxygenase inhibitor35544 An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation.DUKE
EstrogenicAn agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.DUKE
Lipoxygenase inhibitor35856 An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.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
MyorelaxantAn agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.DUKE
Peroxidase inhibitor23924 An agent that blocks the activity of peroxidase enzymes, reducing oxidative stress and inflammation. Therapeutically, it has applications in managing conditions like cancer, neurodegenerative diseases, and cardiovascular disorders, where oxidative damage plays a key role.DUKE
Pigment26130 A biological coloring agent, playing a role in skin and eye protection. Therapeutically, pigments are used in photodynamic therapy and skin camouflage. Medically, they are used to treat conditions like vitiligo, albinism, and skin discoloration, as well as in diagnostic imaging and wound healing applications.DUKE
Quinone-reductase inhibitor23924 An agent that blocks the activity of quinone reductase, an enzyme involved in cellular detoxification and antioxidant processes. It has therapeutic applications in cancer treatment, neuroprotection, and inflammation reduction, with key medical uses including chemotherapy potentiation and neurodegenerative disease management.DUKE
Tyrosine-kinase inhibitor23924 An agent that blocks tyrosine kinase enzymes, reducing cell signaling and proliferation. Therapeutically, it's used to treat cancers, such as leukemia and breast cancer, by inhibiting tumor growth, and also has applications in managing certain autoimmune and inflammatory diseases.DUKE
VasorelaxantAn agent that promotes vasorelaxation, reducing vascular tension and blood pressure. It plays a biological role in regulating blood flow and is therapeutically used to treat hypertension, angina, and heart failure, improving cardiovascular health.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.