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Showing Compound 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
SynonymSource
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
2-(3,4-Dihydroxyphenyl)-3-(b-D-glucopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one, 9CIdb_source
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
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.32%; H 4.34%; O 41.34%DFC
Melting PointMp 238-242°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -19.5 (c, 0.47 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Angiotensin converting enzyme inhibitor35457 An agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.DUKE
Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti-cancer35610 An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.DUKE
Anti elastase23924 An agent that inhibits elastase activity, reducing tissue damage and inflammation. It plays a biological role in protecting tissues from enzymatic degradation. Therapeutically, it is used to manage conditions such as chronic obstructive pulmonary disease (COPD), cystic fibrosis, and acute respiratory distress syndrome (ARDS), where excessive elastase activity contributes to disease progression.DUKE
Anti feedantA substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti nociceptive35470 An agent that reduces the sensitivity to painful stimuli, blocking the transmission of pain signals. Its biological role is to modulate pain perception, with therapeutic applications in managing acute and chronic pain. Key medical uses include treating headaches, arthritis, and post-surgical pain, as well as providing relief for cancer and neuropathic pain.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Anti-retroviral22587 An agent that inhibits the replication of retroviruses, reducing viral load. Therapeutically, it's used to treat and manage retroviral infections, such as HIV/AIDS, by blocking key enzymes like reverse transcriptase, integrase, and protease, thereby preventing disease progression and improving patient outcomes.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Antitumor promoter35610 An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
CapillarigenicAn agent that promotes formation or proliferation of capillaries, enhancing blood flow and tissue oxygenation. It has therapeutic applications in wound healing, cardiovascular health, and tissue repair, with key medical uses in treating ischemic conditions, promoting angiogenesis, and supporting tissue regeneration.DUKE
DiaphoreticAn agent that induces perspiration, playing a biological role in thermoregulation. Therapeutically, it's used to treat fever, detoxify, and relieve congestion. Key medical uses include managing hyperthermia, aiding in toxin removal, and alleviating symptoms of colds and flu.DUKE
Diuretic35498 An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Insectiphile24852 A venom-derived peptide with anti-inflammatory and antimicrobial properties, promoting wound healing and tissue repair. Therapeutically, it has applications in managing infections, reducing inflammation, and accelerating recovery. Key medical uses include wound care, infection control, and tissue regeneration.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
TNF-alpha inhibitor35222 An agent that blocks the activity of tumor necrosis factor-alpha, a pro-inflammatory cytokine, reducing inflammation and immune responses. Therapeutically used to treat autoimmune diseases, such as rheumatoid arthritis, psoriasis, and Crohn's disease, by decreasing inflammation and slowing disease progression.DUKE
Topoisomerase-II inhibitor50750 An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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.