Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2018-05-29 00:54:23 UTC
Primary IDFDB011884
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuercitrin
DescriptionQuercitrin is a glycoside formed from the flavonoid quercetin and the deoxy sugar rhamnose. It is a constituent of the dye quercitron. Quercitrin is found in many foods, some of which are garden tomato (variety), kiwi, italian sweet red pepper, and guava.
CAS Number522-12-3
Structure
Thumb
Synonyms
SynonymSource
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
Mannopyranoside, quercetin-3 6-deoxy-, α-L-biospider
Quercetin 3-O-α-L-rhamnosidebiospider
Quercetin, 3-(6-deoxy-α-L-mannopyranoside)biospider
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053i-9202300000-146a66676d12880b9ed4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-9400018000-24e23b819c75a29c2092View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0024900000-74f4c7623d724538edfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900010-b2ace14e72798df2daf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0uk9-0095000000-fb1f4c76b153f376d777View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0090000000-2e3d10965c5254c3204aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-006x-0090000000-b62d4ed30c4c4ccf8467View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0002-0024900000-74f4c7623d724538edfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0000900010-b2ace14e72798df2daf5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0uk9-0095000000-fb1f4c76b153f376d777View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0090000000-2e3d10965c5254c3204aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 60V, Negativesplash10-006x-0090000000-b62d4ed30c4c4ccf8467View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0009000000-9f1780d23364ab1dcc1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0149000000-45b606d3c459e3e5167aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0000900000-ed00185d5091572af122View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0002900000-87bfc2cd6f8980f4e934View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009100000-8f8d7d2446ccce2143a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0029000000-88da6052a81a4903cd5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uk9-0194000000-078c0ba7b8b4b783e295View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udj-0169600000-924cb5834844dab2b7f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0004900020-af3f3639e76a788d97efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udj-0139800000-b3b8dcc87a1482066b12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0369100000-b2127ae8055c88aadd58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2971000000-1bb8632d2e907de8f3b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-2207900000-85e3b3c257983c10f8c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2339200000-ac76f186c3fd097358ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-5973000000-9e90e5ae59f46fe50f5bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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
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).