Hmdb loader
Show more...Show more...Show more...
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:33:16 UTC
Update Date2022-03-07 02:55:16 UTC
HMDB IDHMDB0037316
Secondary Accession Numbers
  • HMDB37316
Metabolite Identification
Common NameIsoliquiritigenin
DescriptionIsoliquiritigenin 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. Isoliquiritigenin is a bitter tasting compound. Isoliquiritigenin has been detected, but not quantified in, several different foods, such as hibiscus teas (Hibiscus sabbariffa), jicamas (Pachyrhizus erosus), italian sweet red peppers (Capsicum annuum), chinese broccolis (Brassica alboglabra), and squashberries (Viburnum edule). This could make isoliquiritigenin a potential biomarker for the consumption of these foods. Isoliquiritigenin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Isoliquiritigenin.
Structure
Thumb
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 Weight256.2534
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point200 - 204 °CNot Available
Boiling Point504.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility230.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.110 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker164.24530932474
[M+H]+Baker165.04930932474
[M-H]-Not Available164.245http://allccs.zhulab.cn/database/detail?ID=AllCCS00001454
[M+H]+Not Available161.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00001454
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 IDNot Available
Good Scents IDrw1700091
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.. .