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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:11:51 UTC
Update Date2019-07-23 06:25:11 UTC
HMDB IDHMDB0037932
Secondary Accession Numbers
  • HMDB37932
Metabolite Identification
Common 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). Outside of the human body, quercetin 4'-glucoside is found, on average, in the highest concentration in a few different foods, such as garden onions, shallots, and garden onion (var.) and in a lower concentration in . quercetin 4'-glucoside has also been detected, but not quantified in, sweet cherries. This could make quercetin 4'-glucoside a potential biomarker for the consumption of these foods. A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 4'.
Structure
Data?1563863111
Synonyms
ValueSource
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
Chemical FormulaC21H20O12
Average Molecular Weight464.3763
Monoisotopic Molecular Weight464.095476104
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
Traditional Namespiraeoside
CAS Registry Number20229-56-5
SMILES
OC[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
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point240 - 241 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w31-7804900000-dac1de5f80e977a6a3f6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014r-3620009000-b9a475a5880bcb322222Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0190000000-33aab7c5c534e3bd93d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0209000000-8d0c8eda18dc8cceda25Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0udi-0936000000-ead01d21177722db0c04Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-0udi-0942000000-fa589cb74705f9065b0eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0002900001-4dfb6b7d47117fdc7cd5Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009100000-8535cabe8cb5fcb11b9fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0209000000-8d0c8eda18dc8cceda25Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0udi-0936000000-ead01d21177722db0c04Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-0udi-0942000000-fa589cb74705f9065b0eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0002900001-4dfb6b7d47117fdc7cd5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0609200000-9f5f69edfa8bf844814bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0009100000-8535cabe8cb5fcb11b9fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0209000000-8d0c8eda18dc8cceda25Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0936000000-ead01d21177722db0c04Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0942000000-fa589cb74705f9065b0eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0109000000-a98083fb968fef401469Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0119100000-2b8b701588b9f6dc6742Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0119000000-fb6afb6b410e40eaa2f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0118900000-27874bbc8fea14f8f47bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0249100000-73f355fdfebc323cb048Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-3942000000-8b4b6457e00c9e67b74aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-1105900000-5e781c8212fbf2748d27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1139300000-bd6e853b27d25d155e47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-5965000000-96e190b31845aefd3093Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 ID335
FooDB IDFDB017095
KNApSAcK IDC00005387
Chemspider ID4478811
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSpiraeoside
METLIN IDNot Available
PubChem Compound5320844
PDB IDNot Available
ChEBI ID75839
Food Biomarker OntologyNot Available
VMH 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.. .