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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:33:16 UTC
Update Date2021-10-13 07:03:49 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
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, 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
Disposition

Source

Route of exposure

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 Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M-H]-Baker164.24530932474
DeepCCS[M+H]+Baker165.04930932474
AllCCS[M-H]-Not Available164.245http://allccs.zhulab.cn/database/detail?ID=AllCCS00001454
AllCCS[M+H]+Not Available161.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00001454
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.055 g/LALOGPS
logP10(3.04) g/LALOGPS
logP10(3.63) g/LChemAxon
logS10(-3.7) g/LALOGPS
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
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isoliquiritigenin,1TMS,#1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O)C=C2O)C=C12861.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,1TMS,#2C[Si](C)(C)OC1=CC(O)=CC=C1C(=O)/C=C/C1=CC=C(O)C=C12794.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,1TMS,#3C[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O)=C12838.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,2TMS,#1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C)C=C2O)C=C12796.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,2TMS,#2C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O)C=C2O[Si](C)(C)C)C=C12776.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,2TMS,#3C[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C12790.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,3TMS,#1C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C=C12800.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,1TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O)C=C2O)C=C13158.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,1TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1C(=O)/C=C/C1=CC=C(O)C=C13081.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O)=C13118.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,2TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)C=C13390.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,2TBDMS,#2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)C=C13360.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,2TBDMS,#3CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C13306.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Isoliquiritigenin,3TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C=C13614.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isoliquiritigenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1970000000-6164f65f5d6241a006f82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoliquiritigenin GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-1034900000-76ae3aa74bffdff7ee012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoliquiritigenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoliquiritigenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin ESI-TOF 20V, Negative-QTOFsplash10-0a4i-0000009000-afd1640b539ec58a46162017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin ESI-TOF 10V, Negative-QTOFsplash10-0a4i-0000009000-afd1640b539ec58a46162017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin ESI-TOF 20V, Negative-QTOFsplash10-014r-0900000000-e7c4095e90f57884e80c2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin ESI-TOF 10V, Negative-QTOFsplash10-0a4i-0090000000-788e4464b6a542aa7c222017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin LC-ESI-qTOF , Positive-QTOFsplash10-000i-0910000000-15db3efa5c81e3e8fc3e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin LC-ESI-TOF , negative-QTOFsplash10-014r-0900000000-e7c4095e90f57884e80c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin , positive-QTOFsplash10-000i-0910000000-15db3efa5c81e3e8fc3e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin , positive-QTOFsplash10-000i-1930000000-6d143294fc9a6a3430522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin LC-ESI-QFT 17V, positive-QTOFsplash10-000j-0490000000-5d95d877601bf1780cf72020-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin LC-ESI-IT 17V, positive-QTOFsplash10-000j-0970000000-6f6553743b88b6c220e22020-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin 10V, Positive-QTOFsplash10-0a4i-0090000000-6646b871effe2fc1dec42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin 10V, Positive-QTOFsplash10-0a4i-0790000000-a0a66b537f815a68529a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin 30V, Positive-QTOFsplash10-000i-1900000000-f6d8867bba0f74e95f4c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin 50V, Positive-QTOFsplash10-001c-7900000000-d9f65201f86e97a923052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin 50V, Positive-QTOFsplash10-000x-9600000000-4607845a4f3c870a8b7d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin 30V, Positive-QTOFsplash10-000i-1900000000-5b283194f8e6438d1cb42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin 20V, Positive-QTOFsplash10-014r-0900000000-e7c4095e90f57884e80c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin 6V, Positive-QTOFsplash10-0a4r-0690000000-7996084c7a5f231793662021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isoliquiritigenin 10V, Positive-QTOFsplash10-0a4i-0090000000-803b7c0679a83bac81f62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliquiritigenin 10V, Positive-QTOFsplash10-0a4i-0290000000-810f1a7ccbea17d944d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliquiritigenin 20V, Positive-QTOFsplash10-052s-0960000000-9529b79414d923c908732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliquiritigenin 40V, Positive-QTOFsplash10-00ks-4910000000-f074bc6f0bf8212cf9cc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliquiritigenin 10V, Negative-QTOFsplash10-0a4i-0290000000-a373dc716189e73d742c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliquiritigenin 20V, Negative-QTOFsplash10-0a4i-0690000000-12c68dfca23fb3e6405d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoliquiritigenin 40V, Negative-QTOFsplash10-066u-5910000000-ecfe8b4bdcef6eaa160e2016-08-04Wishart LabView Spectrum
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.. .