Quercitrin (CHEM027909)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:04:41 UTC
Update Date2016-11-09 01:18:33 UTC
Accession NumberCHEM027909
Identification
Common NameQuercitrin
ClassSmall Molecule
DescriptionA quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass448.377 g/mol
Monoisotopic Mass448.101 g/mol
CAS Registry Number522-12-3
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
SMILESC[C@@H]1O[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053i-9202300000-146a66676d12880b9ed4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-9400018000-24e23b819c75a29c2092Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0024900000-74f4c7623d724538edfbSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900010-b2ace14e72798df2daf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0uk9-0095000000-fb1f4c76b153f376d777Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0090000000-2e3d10965c5254c3204aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-006x-0090000000-b62d4ed30c4c4ccf8467Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0024900000-74f4c7623d724538edfbSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900010-b2ace14e72798df2daf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0uk9-0095000000-fb1f4c76b153f376d777Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0090000000-2e3d10965c5254c3204aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-006x-0090000000-b62d4ed30c4c4ccf8467Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0149000000-45b606d3c459e3e5167aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0000900000-ed00185d5091572af122Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0002900000-87bfc2cd6f8980f4e934Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009100000-8f8d7d2446ccce2143a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0029000000-88da6052a81a4903cd5eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uk9-0194000000-078c0ba7b8b4b783e295Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udj-0169600000-924cb5834844dab2b7f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0004900020-af3f3639e76a788d97efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0289000000-b59cf2bcc51db51c767dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0001900000-d8ec65a8565b9315fab4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0169400000-2a3b3a4a4e0531e878b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0069400000-99e5a5dc152111b44e48Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udj-0197500000-0470e10f0b43724e37e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0009000000-91492ccad228cf14a895Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0009000000-481378384c8cb997ee55Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0033751
FooDB IDFDB011884
Phenol Explorer IDNot Available
KNApSAcK IDC00005374
BiGG IDNot Available
BioCyc IDQUERCITRIN
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkQuercitrin
Chemspider ID4444112
ChEBI ID17558
PubChem Compound ID5280459
Kegg Compound IDC01750
YMDB IDNot Available
ECMDB IDM2MDB005633
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10963295
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11714358
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11816040
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12008093
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15388977
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15725651
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16806328
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=17366733
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19928818
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21834636
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22327179
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22379948
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23138875
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23291772
15. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.