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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:30:43 UTC
Update Date2021-09-14 15:40:15 UTC
HMDB IDHMDB0033751
Secondary Accession Numbers
  • HMDB33751
Metabolite Identification
Common NameQuercitrin
DescriptionQuercitrin, also known as quercimelin or quercitronic acid, 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. A quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. Quercitrin exists in all living organisms, ranging from bacteria to humans. Quercitrin is found, on average, in the highest concentration within a few different foods, such as lingonberries, american cranberries, and olives and in a lower concentration in common beans, tea, and welsh onions. Quercitrin has also been detected, but not quantified, in several different foods, such as guava, bilberries, common pea, apricots, and spearmints.
Structure
Data?1601242748
Synonyms
ValueSource
3,3',4',5,7-Pentahydroxyflavone-3-L-rhamnosideChEBI
3-((6-Deoxy-alpha-L-mannopyranosyl)-oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
Luteolin 6-deoxy-alpha-L-mannopyranosideChEBI
Quercetin 3-L-rhamnosideChEBI
Quercetin 3-O-alpha-L-rhamnopyranosideChEBI
Quercetin 3-O-rhamnosideChEBI
Quercetin-3-L-rhamnosideChEBI
QuercimelinChEBI
Quercitronic acidChEBI
QuercitrosideChEBI
3-((6-Deoxy-a-L-mannopyranosyl)-oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
3-((6-Deoxy-α-L-mannopyranosyl)-oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
Luteolin 6-deoxy-a-L-mannopyranosideGenerator
Luteolin 6-deoxy-α-L-mannopyranosideGenerator
Quercetin 3-O-a-L-rhamnopyranosideGenerator
Quercetin 3-O-α-L-rhamnopyranosideGenerator
QuercitronateGenerator
3-O-a-L-Rhamnopyranosyloxy-3',4',5,7-tetrahydroxyflavoneHMDB
Flavone, 3,3',4',5, 7-pentahydroxy-, 3-rhamnosideHMDB
Quercetin 3-O-alpha-L-rhamnosideHMDB
Quercetin 3-O-alpha-rhamnopyranosideHMDB
Quercetin 3-O-L-rhamnosideHMDB
Quercetin 3-O-rhamnopyranosideHMDB
Quercetin 3-rhamnosideHMDB
Quercetin, 3-(6-deoxy-alpha-L-mannopyranoside)HMDB
QuercetrinHMDB
3,3',4',5,7-Pentahydroxyflavone 3-alpha-L-rhamnosidePhytoBank
3,3',4',5,7-Pentahydroxyflavone 3-α-L-rhamnosidePhytoBank
3,3’,4’,5,7-Pentahydroxyflavone 3-α-L-rhamnosidePhytoBank
3-O-alpha-L-RhamnopyranosylquercetinPhytoBank
3-O-α-L-RhamnopyranosylquercetinPhytoBank
5,7,3',4'-Tetrahydroxyflavone 3-O-alpha-L-rhamnosidePhytoBank
5,7,3',4'-Tetrahydroxyflavone 3-O-α-L-rhamnosidePhytoBank
5,7,3’,4’-Tetrahydroxyflavone 3-O-α-L-rhamnosidePhytoBank
Quercetin 3-O-α-L-rhamnosidePhytoBank
Quercetin 3-O-α-rhamnopyranosidePhytoBank
Quercetin 3-O-alpha-rhamnosidePhytoBank
Quercetin 3-O-α-rhamnosidePhytoBank
Quercetin 3-alpha-L-rhamnosidePhytoBank
Quercetin 3-α-L-rhamnosidePhytoBank
Quercetin 3-alpha-rhamnosidePhytoBank
Quercetin 3-α-rhamnosidePhytoBank
Quercetin rhamnosidePhytoBank
Chemical FormulaC21H20O11
Average Molecular Weight448.3769
Monoisotopic Molecular Weight448.100561482
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one
Traditional Namequercitrin
CAS Registry Number522-12-3
SMILES
C[C@@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m0/s1
InChI KeyOXGUCUVFOIWWQJ-HQBVPOQASA-N
Chemical Taxonomy
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
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point250 - 252 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.064 mg/mL at 16 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.79 g/LALOGPS
logP1.31ALOGPS
logP0.9ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity107.73 m³·mol⁻¹ChemAxon
Polarizability42.62 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053i-9202300000-146a66676d12880b9ed42017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-9400018000-24e23b819c75a29c20922017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-053i-9202300000-b8aef57836f1cf0f71f72021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0024900000-74f4c7623d724538edfb2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900010-b2ace14e72798df2daf52017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0uk9-0095000000-fb1f4c76b153f376d7772017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0090000000-2e3d10965c5254c3204a2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-006x-0090000000-b62d4ed30c4c4ccf84672017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0024900000-74f4c7623d724538edfb2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900010-b2ace14e72798df2daf52017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0uk9-0095000000-fb1f4c76b153f376d7772017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0090000000-2e3d10965c5254c3204a2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-006x-0090000000-b62d4ed30c4c4ccf84672017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0009000000-9f1780d23364ab1dcc1e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0149000000-45b606d3c459e3e5167a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0000900000-ed00185d5091572af1222017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0002900000-87bfc2cd6f8980f4e9342017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009100000-8f8d7d2446ccce2143a72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0029000000-88da6052a81a4903cd5e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uk9-0194000000-078c0ba7b8b4b783e2952017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udj-0169600000-924cb5834844dab2b7f52017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0004900020-af3f3639e76a788d97ef2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-0139800000-b3b8dcc87a1482066b122016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0369100000-b2127ae8055c88aadd582016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2971000000-1bb8632d2e907de8f3b82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-2207900000-85e3b3c257983c10f8c92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2339200000-ac76f186c3fd097358eb2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-5973000000-9e90e5ae59f46fe50f5b2016-08-03View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, DMSO-d6, experimental)2015-03-12View Spectrum
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 IDNot Available
FooDB IDFDB011884
KNApSAcK IDC00005374
Chemspider ID4444112
KEGG Compound IDC01750
BioCyc IDQUERCITRIN
BiGG IDNot Available
Wikipedia LinkQuercitrin
METLIN IDNot Available
PubChem Compound5280459
PDB IDNot Available
ChEBI ID17558
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB 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.. .