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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:45:15 UTC
Update Date2019-07-23 06:21:34 UTC
HMDB IDHMDB0036595
Secondary Accession Numbers
  • HMDB36595
Metabolite Identification
Common NameLuteone
DescriptionLuteone 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. Luteone has been detected, but not quantified in, several different foods, such as common beans (Phaseolus vulgaris), lima beans (Phaseolus lunatus), pulses, and white lupines (Lupinus albus). This could make luteone a potential biomarker for the consumption of these foods. Luteone 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 small amount of articles have been published on Luteone.
Structure
Data?1563862894
Synonyms
ValueSource
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, MeSH
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
Chemical FormulaC20H18O6
Average Molecular Weight354.3533
Monoisotopic Molecular Weight354.110338308
IUPAC Name3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Traditional Nameluteone
CAS Registry Number41743-56-0
SMILES
CC(C)=CCC1=C(O)C2=C(OC=C(C2=O)C2=C(O)C=C(O)C=C2)C=C1O
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point225 - 227 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Luteone,1TMS,#13326.853https://arxiv.org/abs/1905.12712
Luteone,1TMS,#23355.3728https://arxiv.org/abs/1905.12712
Luteone,1TMS,#33370.002https://arxiv.org/abs/1905.12712
Luteone,1TMS,#43361.891https://arxiv.org/abs/1905.12712
Luteone,2TMS,#13242.9558https://arxiv.org/abs/1905.12712
Luteone,2TMS,#23219.8984https://arxiv.org/abs/1905.12712
Luteone,2TMS,#33216.3467https://arxiv.org/abs/1905.12712
Luteone,2TMS,#43233.3647https://arxiv.org/abs/1905.12712
Luteone,2TMS,#53246.6868https://arxiv.org/abs/1905.12712
Luteone,2TMS,#63230.8652https://arxiv.org/abs/1905.12712
Luteone,3TMS,#13172.604https://arxiv.org/abs/1905.12712
Luteone,3TMS,#23163.6973https://arxiv.org/abs/1905.12712
Luteone,3TMS,#33155.3606https://arxiv.org/abs/1905.12712
Luteone,3TMS,#43163.968https://arxiv.org/abs/1905.12712
Luteone,4TMS,#13161.6292https://arxiv.org/abs/1905.12712
Luteone,1TBDMS,#13651.2786https://arxiv.org/abs/1905.12712
Luteone,1TBDMS,#23634.5457https://arxiv.org/abs/1905.12712
Luteone,1TBDMS,#33642.0522https://arxiv.org/abs/1905.12712
Luteone,1TBDMS,#43655.0686https://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#13770.3115https://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#23763.839https://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#33731.247https://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#43755.837https://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#53782.603https://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#63784.424https://arxiv.org/abs/1905.12712
Luteone,3TBDMS,#13869.422https://arxiv.org/abs/1905.12712
Luteone,3TBDMS,#23826.4407https://arxiv.org/abs/1905.12712
Luteone,3TBDMS,#33847.4758https://arxiv.org/abs/1905.12712
Luteone,3TBDMS,#43886.3342https://arxiv.org/abs/1905.12712
Luteone,4TBDMS,#13995.513https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-2019000000-e7c452eda2f10db25c9c2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-1000039000-76d13aaed8969b7e1f292017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0019000000-cb91f2e2808608ed708b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-3159000000-a8c6a86cb19263f221042016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9784000000-01cb188e86ce2e0005212016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-9551472e266098511e472016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0339000000-a6058217e23e60cb0aea2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6911000000-38814121556ba6c764d52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-b3503695056246b53ddc2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-09ce16917cfa9da615602021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2792000000-ec230273cd7094fcda332021-09-23View 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015507
KNApSAcK IDC00002545
Chemspider ID4445109
KEGG Compound IDC10498
BioCyc IDCPD-6642
BiGG IDNot Available
Wikipedia LinkLuteone_(isoflavone)
METLIN IDNot Available
PubChem Compound5281797
PDB IDNot Available
ChEBI ID27917
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .