Showing Compound Card for Quercitrin (CDB005194)

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Record Information
Version1.0
Created at2020-04-17 19:18:46 UTC
Updated at2020-12-07 19:11:44 UTC
CannabisDB IDCDB005194
Secondary Accession NumbersNot Available
Cannabis Compound 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Quercitrin exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 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. This could make quercitrin a potential biomarker for the consumption of these foods. Quercitrin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight448.38
Monoisotopic Molecular Weight448.1006
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=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 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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSQuercitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053i-9202300000-146a66676d12880b9ed4Spectrum
Predicted GC-MSQuercitrin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9400018000-24e23b819c75a29c2092Spectrum
Predicted GC-MSQuercitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0024900000-74f4c7623d724538edfb2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900010-b2ace14e72798df2daf52017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0uk9-0095000000-fb1f4c76b153f376d7772017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0090000000-2e3d10965c5254c3204a2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-006x-0090000000-b62d4ed30c4c4ccf84672017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0024900000-74f4c7623d724538edfb2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900010-b2ace14e72798df2daf52017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0uk9-0095000000-fb1f4c76b153f376d7772017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0090000000-2e3d10965c5254c3204a2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-006x-0090000000-b62d4ed30c4c4ccf84672017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0149000000-45b606d3c459e3e5167a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0000900000-ed00185d5091572af1222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0002900000-87bfc2cd6f8980f4e9342017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009100000-8f8d7d2446ccce2143a72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0029000000-88da6052a81a4903cd5e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uk9-0194000000-078c0ba7b8b4b783e2952017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udj-0169600000-924cb5834844dab2b7f52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0004900020-af3f3639e76a788d97ef2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0289000000-b59cf2bcc51db51c767d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0001900000-d8ec65a8565b9315fab42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0169400000-2a3b3a4a4e0531e878b92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0069400000-99e5a5dc152111b44e482017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udj-0197500000-0470e10f0b43724e37e92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0009000000-91492ccad228cf14a8952017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0009000000-481378384c8cb997ee552017-09-14View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0033751
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available