Showing Compound Card for Isoquercitrin (CDB005195)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-04-17 19:18:52 UTC
Updated at2020-12-07 19:11:44 UTC
CannabisDB IDCDB005195
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Isoquercitrin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-(3,4-Dihidroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
IsoquercetinChEBI
IsotrifoliinChEBI
2-(3,4-Dihidroxyphenyl)-3-(b-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
2-(3,4-Dihidroxyphenyl)-3-(β-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
2-(3,4-Dihydroxyphenyl)-3-(b-D-glucopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
2-(3,4-Dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneMeSH
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxyMeSH
Flavone, 3,3',4',5,7-pentahydroxy-, 3-beta-D-glucofuranosideMeSH
IsoquercitinMeSH
IsoquercitrosideMeSH
Quercetin 3-(beta-D-glucofuranoside)MeSH
Quercetin 3-O-beta-D-glucofuranosideMeSH
Quercetin-3-O-beta-glucosideMeSH
Quercetin-3-O-glucosideMeSH
Quercetin-3-glucosideMeSH
TrifoliinMeSH
Trifoliin aMeSH
2-(3,4-Dihydroxyphenyl)-3-(b-D-glucopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one, 9ciHMDB
3,3',4',5,7-Pentahydroxyflavone 3-beta-glucosideHMDB
3-Glucopyranosyloxy-3',4',5,7-tetrahydroxyflavoneHMDB
3-GlucosylquercetinHMDB
Glucosyl 3-quercetinHMDB
HirsutrinHMDB
Quercetin 3-beta-D-glucosideHMDB
Quercetin 3-beta-glucosideHMDB
Quercetin 3-beta-O-glucosideHMDB
Quercetin 3-D-glucosideHMDB
Quercetin 3-glucopyranosideHMDB
Quercetin 3-glucosideHMDB
Quercetin 3-monoglucosideHMDB
Quercetin 3-O-glucopyranosideHMDB
Quercetin 3-O-glucosideHMDB
Quercetol 3-glucosideHMDB
Quercetol 3-monoglucosideHMDB
IsoquercitrinChEBI
Quercetin 3-O-b-D-glucopyranosideGenerator
Quercetin 3-O-β-D-glucopyranosideGenerator
3-O-beta-D-GlucopyranosylquercetinPhytoBank
3-O-β-D-GlucopyranosylquercetinPhytoBank
3-beta-D-GlucosylquercetinPhytoBank
3-β-D-GlucosylquercetinPhytoBank
3',4',5,7-Tetrahydroxyflavone-3-beta-D-glucopyranosidePhytoBank
3',4',5,7-Tetrahydroxyflavone-3-β-D-glucopyranosidePhytoBank
3’,4’,5,7-Tetrahydroxyflavone-3-β-D-glucopyranosidePhytoBank
Contigoside BPhytoBank
Glucosyl-3-quercetinPhytoBank
IsoquercetrinPhytoBank
Quercetin 3-O-beta-D-glucopyranosidePhytoBank
Quercetin 3-O-beta-D-glucosidePhytoBank
Quercetin 3-O-β-D-glucosidePhytoBank
Quercetin 3-O-beta-glucosidePhytoBank
Quercetin 3-O-β-glucosidePhytoBank
Quercetin 3-mono-D-glucosidePhytoBank
Quercetin 3-beta-D-glucopyranosidePhytoBank
Quercetin 3-β-D-glucopyranosidePhytoBank
Quercetin 3-β-D-glucosidePhytoBank
Quercetin 3beta-O-glucosidePhytoBank
Quercetin 3β-O-glucosidePhytoBank
Quercetin 3beta-glucosidePhytoBank
Quercetin 3β-glucosidePhytoBank
Quercetin glucosidePhytoBank
Quercetin-3-glucosePhytoBank
Quercetin-3-beta-glucopyranosidePhytoBank
Quercetin-3-β-glucopyranosidePhytoBank
Chemical FormulaC21H20O12
Average Molecular Weight464.38
Monoisotopic Molecular Weight464.0955
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
Traditional Nameisoquercitin
CAS Registry Number482-35-9
SMILES
OC[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
InChI Identifier
InChI=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
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
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point238 - 242 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0037362
DrugBank IDDB12665
Phenol Explorer Compound ID293
FoodDB IDFDB016389
KNApSAcK IDC00005373
Chemspider ID4444361
KEGG Compound IDC05623
BioCyc IDCPD1F-437
BiGG IDNot Available
Wikipedia LinkIsoquercetin
METLIN IDNot Available
PubChem Compound5280804
PDB IDNot Available
ChEBI ID68352
References
General ReferencesNot Available