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Isoquercitrin (FDB016389)

Record Information
Version1.0
Creation date2010-04-08 22:12:24 UTC
Update date2020-09-17 15:41:03 UTC
Primary IDFDB016389
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoquercitrin
DescriptionIsoquercitrin, also known as isotrifoliin or hirsutrin, 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. Isoquercitrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isoquercitrin has been detected, but not quantified in, green vegetables and root vegetables. This could make isoquercitrin a potential biomarker for the consumption of these foods. Isoquercitrin has been used in trials studying the treatment of Kidney Cancer, Renal cell carcinoma, Advanced Renal Cell Carcinoma, Thromboembolism of Vein in Pancreatic Cancer, and Thromboembolism of Vein VTE in Colorectal Cancer, among others.
CAS Number482-35-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.95 g/LALOGPS
logP0.47ALOGPS
logP-0.14ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.28 m³·mol⁻¹ChemAxon
Polarizability43.56 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H20O12
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1
InChI KeyOVSQVDMCBVZWGM-QSOFNFLRSA-N
Isomeric SMILESOC[C@H]1O[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight464.3763
Monoisotopic Molecular Weight464.095476104
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
  • Phenol
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsoquercitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uea-8903800000-499ac85a438f6221151eSpectrum
Predicted GC-MSIsoquercitrin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014r-3620009000-aa92fb234d45c04fb4a1Spectrum
Predicted GC-MSIsoquercitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsoquercitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0009000000-5b33a5f16f6e2b064a262017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0000900000-04fd0a90f823358ed6802017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0001900000-a884073b5df03fc34d442017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009200000-abf468a3d736431e673c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0019000000-6c4a0f0151f89b993af72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uk9-0096000000-2a8faa231ffe4833d3e52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0w29-0179700000-4feff1360b5c3797e9452017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0003900002-fb997b013c890e4beb252017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0059000000-f059e0c8ce382613a8af2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0000900000-2ca67c601c5cd16acf0e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0079400000-53c1ad9f9a822003ead82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0w29-0029400000-e04499260d75d9c877842017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009200000-57d1b2e15f55ae8093852017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-0ac33fff6c0d20867fa42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-6b8e2bdefa584c75e6c62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-dff25d3afe49ed2abe872017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-29733c57848cecc33e702017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-06624a60d6ef7aa134bb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0109000000-cfa8aaba41883dcf51e52017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0238900000-84d67141521459a118c02016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0269100000-855726a927e888161d782016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2962000000-bc39b0d9e5586054d85f2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-1306900000-12c0a6f0c9db05e8c9bd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2439200000-fc56cb8d8bcb486e96a62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-6963000000-3bde95e6420d1d4a73e42016-08-03View Spectrum
NMRNot Available
ChemSpider ID4444361
ChEMBL IDCHEMBL250450
KEGG Compound IDC05623
Pubchem Compound ID5280804
Pubchem Substance IDNot Available
ChEBI ID28299
Phenol-Explorer ID293
DrugBank IDNot Available
HMDB IDHMDB37362
CRC / DFC (Dictionary of Food Compounds) IDKQX79-A:KQX79-A
EAFUS IDNot Available
Dr. Duke IDHIRSUTRIN|ISOQUERCITRIN|ISOQUERCETIN|QUERCETIN-3-O-GLUCOSIDE|QUERCETIN-3-O-BETA-D-GLUCOSIDE|3-O-BETA-D-QUERCETIN-GLUCOSIDE|QUERCETIN-3-O-BETA-GLUCOSIDE|QUERCETIN-3-BETA-D-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00005373
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1588881
SuperScent IDNot Available
Wikipedia IDIsoquercitrin
Phenol-Explorer Metabolite ID293
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
EggplantExpected but not quantifiedNot AvailableAjay P. Singh, Devanand Luthria b, Ted Wilson, Nicholi Vorsa, Vartika Singh, Gary S. Banuelos, Sajeemas Pasakdee. Polyphenols content and antioxidant capacity of eggplant pulp. Food Chemistry 114 (2009) 955-975, PATHBANK
Broccoli1.800 - 1.800 mg/100 g1.800 mg/100 gPHENOL EXPLORER, PHYTOHUB, PATHBANK
CarrotExpected but not quantifiedNot AvailableDUKE, PATHBANK
DillExpected but not quantifiedNot AvailableDUKE, PATHBANK
Garden onion2.000 - 2.000 mg/100 g2.000 mg/100 gDUKE, PATHBANK
ParsnipExpected but not quantifiedNot AvailableDUKE, PATHBANK
PotatoExpected but not quantifiedNot AvailableDUKE, KNAPSACK, PATHBANK
Red raspberry0.28269 - 3.59082 mg/100 g2.283 mg/100 gPHENOL EXPLORER, DUKE, PATHBANK
Sea-buckthornberry0.83500 - 0.83500 mg/100 g0.83500 mg/100 gPHENOL EXPLORER, PATHBANK
BarleyExpected but not quantifiedNot AvailablePATHBANK
Showing 1 to 10 of 35 entries
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.