Record Information
Version1.0
Creation date2010-04-08 22:11:53 UTC
Update date2019-11-26 03:11:43 UTC
Primary IDFDB015507
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLuteone
DescriptionLuteone, also known as ruizgenin, belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, luteone is considered to be a flavonoid lipid molecule. Luteone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Luteone has been detected, but not quantified in, several different foods, such as common beans, lima beans, pulses, and white lupines. This could make luteone a potential biomarker for the consumption of these foods.
CAS Number41743-56-0
Structure
Thumb
Synonyms
SynonymSource
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-oneChEBI
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ciHMDB
Luteone?HMDB
RuizgeninHMDB
Ruizgenin, (3beta,5alpha,6alpha,25R)-isomerMeSH
Ruizgenin, (3beta,5alpha,6alpha,25S)-isomerMeSH
5 beta-Spirostane-3 beta,6 alpha-diolMeSH
Ruizgenin, (3beta,5alpha,6beta,25R)-isomerMeSH
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CIdb_source
Luteonebiospider
Luteone (isoflavone)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.26ALOGPS
logP4.5ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)6.41ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.91 m³·mol⁻¹ChemAxon
Polarizability37.01 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H18O6
IUPAC name3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C20H18O6/c1-10(2)3-5-13-16(23)8-17-18(19(13)24)20(25)14(9-26-17)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3
InChI KeyMMPVAPMCVABQPS-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCC1=C(O)C2=C(OC=C(C2=O)C2=C(O)C=C(O)C=C2)C=C1O
Average Molecular Weight354.3533
Monoisotopic Molecular Weight354.110338308
Classification
Description Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct Parent6-prenylated isoflavanones
Alternative Parents
Substituents
  • 6-prenylated isoflavanone
  • Hydroxyisoflavonoid
  • Isoflavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 PointMp 225-227°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data337 () (MeOH-NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLuteone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004l-2019000000-e7c452eda2f10db25c9cSpectrum
Predicted GC-MSLuteone, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-1000039000-76d13aaed8969b7e1f29Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0019000000-cb91f2e2808608ed708bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-3159000000-a8c6a86cb19263f22104Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9784000000-01cb188e86ce2e000521Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-9551472e266098511e47Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0339000000-a6058217e23e60cb0aeaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6911000000-38814121556ba6c764d5Spectrum
NMRNot Available
ChemSpider ID4445109
ChEMBL IDCHEMBL549617
KEGG Compound IDC10498
Pubchem Compound ID5281797
Pubchem Substance IDNot Available
ChEBI ID27917
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36595
CRC / DFC (Dictionary of Food Compounds) IDKCW78-A:KCW78-A
EAFUS IDNot Available
Dr. Duke IDLUTEONE
BIGG IDNot Available
KNApSAcK IDC00002545
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).