CHEBI:68352 - quercetin 3-O-β-D-glucopyranoside

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ChEBI Name quercetin 3-O-β-D-glucopyranoside
ChEBI ID CHEBI:68352
ChEBI ASCII Name quercetin 3-O-beta-D-glucopyranoside
Definition A quercetin O-glucoside that is quercetin with a β-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H20O12
Net Charge 0
Average Mass 464.37630
Monoisotopic Mass 464.09548
InChI 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
InChIKey OVSQVDMCBVZWGM-QSOFNFLRSA-N
SMILES OC[C@H]1O[C@@H](Oc2c(oc3cc(O)cc(O)c3c2=O)-c2ccc(O)c(O)c2)[C@H](O)[C@@H](O)[C@@H]1O
Metabolite of Species Details
Vitis vinifera (NCBI:txid29760) See: MetaboLights Study
Vitis vinifera (NCBI:txid29760) See: DOI
Lepisorus contortus (NCBI:txid699669) Found in whole plant (BTO:0001461). 95% EtOH extract of air-dried, powdered whole plant See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
osteogenesis regulator
Any compound that induces or regulates osteogenesis.
histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
Application(s): bone density conservation agent
An agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis.
histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
antipruritic drug
A drug, usually applied topically, that relieves pruritus (itching).
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) has functional parent β-D-glucose (CHEBI:15903)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) has role antineoplastic agent (CHEBI:35610)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) has role antioxidant (CHEBI:22586)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) has role antipruritic drug (CHEBI:59683)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) has role bone density conservation agent (CHEBI:50646)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) has role histamine antagonist (CHEBI:37956)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) has role osteogenesis regulator (CHEBI:63054)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) has role plant metabolite (CHEBI:76924)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) is a β-D-glucoside (CHEBI:22798)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) is a monosaccharide derivative (CHEBI:63367)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) is a quercetin O-glucoside (CHEBI:64621)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) is a tetrahydroxyflavone (CHEBI:38684)
quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) is conjugate acid of quercetin 3-O-β-D-glucopyranoside(1−) (CHEBI:144437)
Incoming quercetin 3-O-β-D-glucopyranoside(1−) (CHEBI:144437) is conjugate base of quercetin 3-O-β-D-glucopyranoside (CHEBI:68352)
IUPAC Name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl β-D-glucopyranoside
Synonyms Sources
2-(3,4-Dihidroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one KEGG COMPOUND
2-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one ChEBI
isoquercetin ChEBI
Isoquercitrin KEGG COMPOUND
Isotrifoliin KEGG COMPOUND
Manual Xrefs Databases
C00005373 KNApSAcK
C05623 KEGG COMPOUND
HMDB0037362 HMDB
Isoquercetin Wikipedia
LSM-5818 LINCS
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Registry Numbers Types Sources
100989 Reaxys Registry Number Reaxys
21637-25-2 CAS Registry Number KEGG COMPOUND
482-35-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21261296 PubMed citation Europe PMC
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31870463 PubMed citation Europe PMC
Last Modified
29 July 2020
General Comment
2020-07-29 The glucose moiety in this structure is in the pyranose (6-membered ring) form. There is a separate entry where the glucose moiety is in the furanose (5-membered ring form, CHEBI:28299.