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Quercitrin (FDB011884)

Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2020-09-17 15:41:02 UTC
Primary IDFDB011884
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number522-12-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not 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
Chemical FormulaC21H20O11
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
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
Isomeric 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
Average Molecular Weight448.3769
Monoisotopic Molecular Weight448.100561482
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.25%; H 4.50%; O 39.25%DFC
Melting PointMp 250-252° (anhyd.)DFC
Boiling PointNot Available
Experimental Water Solubility0.064 mg/mL at 16 oCSEIDELL,A (1941)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]15D -158 (c, 0.61 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
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
ChemSpider ID4444112
ChEMBL IDCHEMBL82242
KEGG Compound IDC01750
Pubchem Compound ID5280459
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID295
DrugBank IDNot Available
HMDB IDHMDB33751
CRC / DFC (Dictionary of Food Compounds) IDHBN30-Z:HBN30-Z
EAFUS IDNot Available
Dr. Duke IDQUERCETIN-3-RHAMNOSIDE|QUERCITRIN|QUERCETRIN|QUERCETIN-3-O-RHAMNOSIDE|QUERCITIN-3-RHAMNOSIDE
BIGG IDNot Available
KNApSAcK IDC00005374
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDQuercitrin
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
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
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
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti complementaryDUKE
anti edemicDUKE
anti feedantDUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hemorrhagic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti mutagenicDUKE
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
anti purpuric50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti thrombogenic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cholereticDUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
cyclooxygenase activatorDUKE
detoxicant50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
dye37958 DUKE
hemostatDUKE
hepatotonicDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
hypotensiveDUKE
Insectiphile24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
monoamine-oxidase-A inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
monoamine-oxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
paralyticDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
vasopressorDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— 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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).