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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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point225 - 227 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP10(3.26) g/LALOGPS
logP10(4.5) g/LChemAxon
logS10(-4.3) g/LALOGPS
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

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Luteone,1TMS,#1CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O[Si](C)(C)C3326.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,1TMS,#2CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C)C(=O)C2=C1O3355.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,1TMS,#3CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O)C(=O)C2=C1O3370.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,1TMS,#4CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O3361.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TMS,#1CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O[Si](C)(C)C3243.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TMS,#2CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O)C(=O)C2=C1O[Si](C)(C)C3219.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TMS,#3CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C3216.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TMS,#4CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C)C(=O)C2=C1O3233.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TMS,#5CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C2=C1O3246.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TMS,#6CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O)C(=O)C2=C1O3230.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,3TMS,#1CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O)C(=O)C2=C1O[Si](C)(C)C3172.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,3TMS,#2CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C3163.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,3TMS,#3CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C3155.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,3TMS,#4CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C2=C1O3164.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,4TMS,#1CC(C)=CCC1=C(O[Si](C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C3161.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,1TBDMS,#1CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3651.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,1TBDMS,#2CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O3634.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,1TBDMS,#3CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C2=C1O3642.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,1TBDMS,#4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O3655.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3770.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#2CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3763.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#3CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3731.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O3755.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#5CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O3782.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,2TBDMS,#6CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C2=C1O3784.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,3TBDMS,#1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3869.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,3TBDMS,#2CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3826.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,3TBDMS,#3CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3847.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,3TBDMS,#4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O3886.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Luteone,4TBDMS,#1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C3995.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Luteone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-2019000000-e7c452eda2f10db25c9c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Luteone GC-MS (4 TMS) - 70eV, Positivesplash10-004i-1000039000-76d13aaed8969b7e1f292017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Luteone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 10V, Positive-QTOFsplash10-0a4i-0019000000-cb91f2e2808608ed708b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 20V, Positive-QTOFsplash10-05mk-3159000000-a8c6a86cb19263f221042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 40V, Positive-QTOFsplash10-0gb9-9784000000-01cb188e86ce2e0005212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 10V, Negative-QTOFsplash10-0udi-0009000000-9551472e266098511e472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 20V, Negative-QTOFsplash10-0udi-0339000000-a6058217e23e60cb0aea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 40V, Negative-QTOFsplash10-0a4i-6911000000-38814121556ba6c764d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 10V, Negative-QTOFsplash10-0udi-0009000000-b3503695056246b53ddc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 20V, Negative-QTOFsplash10-0udi-0019000000-09ce16917cfa9da615602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 40V, Negative-QTOFsplash10-001i-2792000000-ec230273cd7094fcda332021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 10V, Positive-QTOFsplash10-0002-0090000000-0e40d1dc69d66b6011272021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 20V, Positive-QTOFsplash10-0002-0090000000-f95cd7f394c37bd651112021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Luteone 40V, Positive-QTOFsplash10-009t-0190000000-062259ae8fdd318edbaf2021-09-24Wishart 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 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
Good Scents 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.. .