Record Information
Version1.0
Creation date2010-04-08 22:15:25 UTC
Update date2019-11-26 03:19:47 UTC
Primary IDFDB021034
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(+)-Lyoniresinol 9-glucoside
Description(+)-Lyoniresinol 9-glucoside belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones (+)-Lyoniresinol 9-glucoside has been detected, but not quantified in, fruits. This could make (+)-lyoniresinol 9-glucoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (+)-Lyoniresinol 9-glucoside.
CAS Number109-04-6
Structure
Thumb
Synonyms
SynonymSource
(+)-Lyoniresinol 9-glucosidemanual
(+)-Lyoniresinol 9-O-b-D-glucopyranosidemanual
Predicted Properties
PropertyValueSource
Water Solubility0.43 g/LALOGPS
logP0.23ALOGPS
logP-0.31ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.24ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area196.99 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity143.21 m³·mol⁻¹ChemAxon
Polarizability59.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H38O13
IUPAC name2-{[6-hydroxy-4-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-5,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
InChI IdentifierInChI=1S/C28H38O13/c1-36-16-7-13(8-17(37-2)22(16)31)20-15(9-29)14(5-12-6-18(38-3)24(33)27(39-4)21(12)20)11-40-28-26(35)25(34)23(32)19(10-30)41-28/h6-8,14-15,19-20,23,25-26,28-35H,5,9-11H2,1-4H3
InChI KeyPACBNJFGEWTGCE-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1C(CO)C(COC2OC(CO)C(O)C(O)C2O)CC2=CC(OC)=C(O)C(OC)=C12
Average Molecular Weight582.5935
Monoisotopic Molecular Weight582.231241302
Classification
Description Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassLignan glycosides
Sub ClassNot Available
Direct ParentLignan glycosides
Alternative Parents
Substituents
  • Lignan glycoside
  • 1-aryltetralin lignan
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Methoxyphenol
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Tetralin
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Phenol
  • Alkyl aryl ether
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organooxygen compound
  • Alcohol
  • Primary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.73%; H 6.57%; O 35.70%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]27D -51.7 (c, 0.41 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0mbi-6401290000-1a96a63a2005c7bf77a2Spectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dr-9311116000-2bf97845bfda71cf4b5cSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, "(+)-Lyoniresinol 9-glucoside,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(+)-Lyoniresinol 9-glucoside, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gc0-0102590000-f30abc495174edacc266Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0304940000-97179cedefc560ef47f9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4307970000-2781beacfc4abde50442Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-1200390000-d5aba701e09ee894f8feSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4502490000-a67e0f7710731185dd7aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9102520000-37e0958a6eed0f998680Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0014920000-0cc0ef9b54ddf946beb1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0004910000-1a55bebcdc8b2b28141aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-1349600000-f46b364c98a7cb6a2bb8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gx0-0101590000-27cb713da7bc080d0a83Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-3014960000-f9ac2c33ee660cc3d63bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kbs-3009560000-5a4d8c06ad0d02524020Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41148
CRC / DFC (Dictionary of Food Compounds) IDLKJ46-R:NKD55-L
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference