Record Information
Version1.0
Creation date2010-04-08 22:10:09 UTC
Update date2019-11-26 03:06:42 UTC
Primary IDFDB012398
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLicoisoflavone A
DescriptionLicoisoflavone A, also known as phaseoluteone, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, licoisoflavone a is considered to be a flavonoid lipid molecule. Licoisoflavone A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Licoisoflavone A has been detected, but not quantified in, several different foods, such as oats, quinoa, millets, triticales, and common buckwheats. This could make licoisoflavone a a potential biomarker for the consumption of these foods.
CAS Number66056-19-7
Structure
Thumb
Synonyms
SynonymSource
2',4',5,7-Tetrahydroxy-3'-(3,3-dimethylallyl)isoflavoneChEBI
PhaseoluteoneChEBI
3'-Isopentenyl-2',4',5,7-tetrahydroxyisoflavoneHMDB
LicoisoflavoneHMDB
[2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one, 9ciHMDB
[2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-4H-1-benzopyran-4-onedb_source
Licoisoflavone Adb_source
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.29ALOGPS
logP4.5ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)6.54ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.91 m³·mol⁻¹ChemAxon
Polarizability36.83 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H18O6
IUPAC name3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C20H18O6/c1-10(2)3-4-13-15(22)6-5-12(19(13)24)14-9-26-17-8-11(21)7-16(23)18(17)20(14)25/h3,5-9,21-24H,4H2,1-2H3
InChI KeyKCUZCRLRQVRBBV-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCC1=C(O)C(=CC=C1O)C1=COC2=C(C(O)=CC(O)=C2)C1=O
Average Molecular Weight354.358
Monoisotopic Molecular Weight354.1103383
Classification
Description Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflav-2-enes
Direct ParentIsoflavones
Alternative Parents
Substituents
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Resorcinol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.79%; H 5.12%; O 27.09%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLicoisoflavone A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004u-2019000000-2f739f3452171f905be2Spectrum
Predicted GC-MSLicoisoflavone A, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-1000049000-7018f194d1008ff5433dSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-62f92498db843c9e5858Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ot-3349000000-ed8805f32a0bbcd8f235Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gba-8952000000-6c41fa9ae3eca464c67bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0109000000-be91e8e91b4067f6ed22Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0918000000-fb711c0f7e6d3a6949feSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pki-2921000000-ec8a5e470e5efab9b710Spectrum
NMRNot Available
ChemSpider ID4445102
ChEMBL IDNot Available
KEGG Compound IDC10486
Pubchem Compound ID5281789
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34125
CRC / DFC (Dictionary of Food Compounds) IDHGS69-Z:HGS69-Z
EAFUS IDNot Available
Dr. Duke IDLICOISOFLAVONE-A|PHASEOLUTEONE
BIGG IDNot Available
KNApSAcK IDC00002542
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti feedantDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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.