Isoliquiritigenin (CHEM030821)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:11:37 UTC
Update Date2016-11-09 01:19:09 UTC
Accession NumberCHEM030821
Identification
Common NameIsoliquiritigenin
ClassSmall Molecule
DescriptionA member of the class of chalcones that is trans-chalcone hydroxylated at C-2', -4 and -4'.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical 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 Mass256.253 g/mol
Monoisotopic Mass256.074 g/mol
CAS Registry Number961-29-5
IUPAC Name(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Traditional Nameisoliquiritigenin
SMILESOC1=CC=C(\C=C\C(=O)C2=CC=C(O)C=C2O)C=C1
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1970000000-6164f65f5d6241a006f8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-1034900000-76ae3aa74bffdff7ee01Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0000009000-afd1640b539ec58a4616Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0000009000-afd1640b539ec58a4616Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0900000000-e7c4095e90f57884e80cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0090000000-788e4464b6a542aa7c22Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTOF , Positivesplash10-000i-0910000000-15db3efa5c81e3e8fc3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014r-0900000000-e7c4095e90f57884e80cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0910000000-15db3efa5c81e3e8fc3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-1930000000-6d143294fc9a6a343052Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 17V, positivesplash10-000j-0490000000-5d95d877601bf1780cf7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 17V, positivesplash10-000j-0970000000-6f6553743b88b6c220e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-6646b871effe2fc1dec4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0790000000-a0a66b537f815a68529aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-1900000000-f6d8867bba0f74e95f4cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-001c-7900000000-d9f65201f86e97a92305Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000x-9600000000-4607845a4f3c870a8b7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-1900000000-5b283194f8e6438d1cb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014r-0900000000-e7c4095e90f57884e80cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4r-0690000000-7996084c7a5f23179366Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-803b7c0679a83bac81f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-810f1a7ccbea17d944d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052s-0960000000-9529b79414d923c90873Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ks-4910000000-f074bc6f0bf8212cf9ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0290000000-a373dc716189e73d742cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0690000000-12c68dfca23fb3e6405dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-5910000000-ecfe8b4bdcef6eaa160eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03285
HMDB IDHMDB0037316
FooDB IDFDB016335
Phenol Explorer IDNot Available
KNApSAcK IDC00006925
BiGG IDNot Available
BioCyc IDCPD-3041
METLIN IDNot Available
PDB IDHCC
Wikipedia LinkIsoliquiritigenin
Chemspider ID553829
ChEBI ID310312
PubChem Compound ID638278
Kegg Compound IDC08650
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11501051
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11853176
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14510590
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14640516
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15878356
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=1622242
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16675659
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19067384
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=20146476
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21158449
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21691759
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21720042
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21815175
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=21866899
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=21945440
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22076338
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=9525107
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.