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Showing Compound Quercetin 4'-glucoside (FDB017095)

Record Information
Version1.0
Creation date2010-04-08 22:12:50 UTC
Update date2019-11-26 03:14:11 UTC
Primary IDFDB017095
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuercetin 4'-glucoside
DescriptionQuercetin 4'-glucoside, also known as spiraeoside or spiraein, belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Quercetin 4'-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Quercetin 4'-glucoside is found, on average, in the highest concentration within a few different foods, such as garden onions, shallots, and garden onion (var.). Quercetin 4'-glucoside has also been detected, but not quantified in, sweet cherries and yali pears. This could make quercetin 4'-glucoside a potential biomarker for the consumption of these foods.
CAS Number20229-56-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
SpiraeinChEBI
SpiraeosideChEBI
Quercetin 4'-O-beta-D-glucopyranosideHMDB
Quercetin 4'-O-beta-D-glucosideHMDB
Quercetin 4'-O-glucosideHMDB
SpiraeosidHMDB
Spireoside (6ci,7ci,8ci)HMDB
Quercetin 4'-O-b-D-glucopyranosideGenerator
Quercetin 4'-O-β-D-glucopyranosideGenerator
Quercetin-4'-glucosideMeSH
3,3',4',5,7-Pentahydroxyflavone 4'-O-b-D-glucopyranosidemanual
Quercetin 4'-glucosidedb_source
Spireoside (6CI,7CI,8CI)manual
Predicted Properties
PropertyValueSource
Water Solubility1.59 g/LALOGPS
logP0.63ALOGPS
logP-0.11ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)6.44ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.01 m³·mol⁻¹ChemAxon
Polarizability44.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H20O12
IUPAC name3,5,7-trihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)32-11-2-1-7(3-9(11)24)20-18(29)16(27)14-10(25)4-8(23)5-12(14)31-20/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1
InChI KeyOIUBYZLTFSLSBY-HMGRVEAOSA-N
Isomeric SMILESOC[C@H]1O[C@@H](OC2=CC=C(C=C2O)C2=C(O)C(=O)C3=C(O2)C=C(O)C=C3O)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight464.3763
Monoisotopic Molecular Weight464.095476104
Classification
Description belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid o-glycoside
  • Flavonoid-4p-o-glycoside
  • 3-hydroxyflavone
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenol ether
  • Phenoxy compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 54.32%; H 4.34%; O 41.34%DFC
Melting PointMp 240-241° (209-210°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]17D -69 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w31-7804900000-dac1de5f80e977a6a3f6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014r-3620009000-b9a475a5880bcb322222JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0190000000-33aab7c5c534e3bd93d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0209000000-8d0c8eda18dc8cceda25JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0udi-0936000000-ead01d21177722db0c04JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-0udi-0942000000-fa589cb74705f9065b0eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0002900001-4dfb6b7d47117fdc7cd5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009100000-8535cabe8cb5fcb11b9fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0209000000-8d0c8eda18dc8cceda25JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0udi-0936000000-ead01d21177722db0c04JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-0udi-0942000000-fa589cb74705f9065b0eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0002900001-4dfb6b7d47117fdc7cd5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0609200000-9f5f69edfa8bf844814bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009100000-8535cabe8cb5fcb11b9fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0209000000-8d0c8eda18dc8cceda25JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0936000000-ead01d21177722db0c04JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0942000000-fa589cb74705f9065b0eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0109000000-a98083fb968fef401469JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0119100000-2b8b701588b9f6dc6742JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0119000000-fb6afb6b410e40eaa2f7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0118900000-27874bbc8fea14f8f47bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0249100000-73f355fdfebc323cb048JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-3942000000-8b4b6457e00c9e67b74aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-1105900000-5e781c8212fbf2748d27JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1139300000-bd6e853b27d25d155e47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-5965000000-96e190b31845aefd3093JSpectraViewer
ChemSpider ID4478811
ChEMBL IDCHEMBL402947
KEGG Compound IDNot Available
Pubchem Compound ID5320844
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID335
DrugBank IDNot Available
HMDB IDHMDB37932
CRC / DFC (Dictionary of Food Compounds) IDHBR39-C:KWD91-S
EAFUS IDNot Available
Dr. Duke IDSPIRAEOSIDE|QUERCETIN-4-O-BETA-D-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00005387
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSpiraeoside
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
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
quinone-reductase inducerDUKE
anti neoplastic35610 A substance that inhibits or prevents the proliferation of neoplasms.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— 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.