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Showing Compound Quercetin 3-O-glucosyl-rhamnosyl-galactoside (FDB000166)

Record Information
Version1.0
Creation date2010-04-08 22:04:28 UTC
Update date2019-11-26 02:54:33 UTC
Primary IDFDB000166
Secondary Accession Numbers
  • FDB018939
Chemical Information
FooDB NameQuercetin 3-O-glucosyl-rhamnosyl-galactoside
DescriptionHyperin 6''-[glucosyl-(1->3)-rhamnoside], also known as Q-glu-rha-gal or quercetin-3-glu-rha-gal, is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Hyperin 6''-[glucosyl-(1->3)-rhamnoside] is soluble (in water) and a very weakly acidic compound (based on its pKa). Hyperin 6''-[glucosyl-(1->3)-rhamnoside] can be found in tea, which makes hyperin 6''-[glucosyl-(1->3)-rhamnoside] a potential biomarker for the consumption of this food product.
CAS Number134953-93-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility10.4 g/LALOGPS
logP-0.56ALOGPS
logP-2.6ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area344.67 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity172.56 m³·mol⁻¹ChemAxon
Polarizability71.82 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC33H40O21
IUPAC name3-{[(2S,3R,4S,5R,6R)-6-({[(2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C33H40O21/c1-9-19(39)29(53-32-25(45)23(43)20(40)16(7-34)51-32)27(47)31(49-9)48-8-17-21(41)24(44)26(46)33(52-17)54-30-22(42)18-14(38)5-11(35)6-15(18)50-28(30)10-2-3-12(36)13(37)4-10/h2-6,9,16-17,19-21,23-27,29,31-41,43-47H,7-8H2,1H3/t9-,16+,17+,19-,20+,21-,23-,24-,25+,26+,27+,29+,31+,32-,33-/m0/s1
InChI KeyXEFNBVWDOQCMSG-GJHFDJSNSA-N
Isomeric SMILESC[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O
Average Molecular Weight772.6581
Monoisotopic Molecular Weight772.206208342
Classification
Description Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Oligosaccharide
  • Flavonoid-3-o-glycoside
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Oxane
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TMS_1_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuercetin 3-O-glucosyl-rhamnosyl-galactoside, TBDMS_1_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfu-0229242700-837287fef306f32433d12016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0239221000-e383ee46007c9d97e1192016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0739010100-2bfde76ca832b6b1d7272016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-2349412800-8a33740a029e9d9e866e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1329111100-1ae22db2885dbbeeb8382016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2649000000-4fadc36e7c6ee8473f7c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000200-0beb8c5f0064cf6981c52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ur0-0009000900-97e56086872ef552eae32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0009000000-58b2754f892c40f076992021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000900-ec3d348581783841d73a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0005000900-06a06e12d9d999109ccf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0019000100-6b0b22c02d3a0356199c2021-09-24View Spectrum
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 ID323
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
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
Processing...
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— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.