quercetin 3-O-beta-D-glucopyranoside (CHEBI:68352)

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

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ChEBI ID	CHEBI:68352
ChEBI Name	quercetin 3-O-β-D-glucopyranoside
Stars
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
Last Modified	27 October 2021
Downloads	Molfile

Formula	C21H20O12
Net Charge	0
Average Mass	464.379
Monoisotopic Mass	464.09548
SMILES	O=c1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(-c2ccc(O)c(O)c2)oc2cc(O)cc(O)c12
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

Wikipedia

Species of Metabolite	Component	Source	Comments
Lepisorus contortus (ncbitaxon:699669)	whole plant (BTO:0001461)	PubMed (21261296)	95% EtOH extract of air-dried, powdered whole plant
Vitis vinifera (ncbitaxon:29760)
	-	MetaboLights (MTBLS55)
	-	DOI (10.1007/s11306-014-0638-x)

Roles Classification

Chemical Role:	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:	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. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. 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. 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. antipruritic drug A drug, usually applied topically, that relieves pruritus (itching).

ChEBI Ontology

Outgoing Relation(s)
	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 geroprotector (CHEBI:176497)
	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 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 a β-D-glucoside (CHEBI:22798)
	quercetin 3-O-β-D-glucopyranoside (CHEBI:68352) is conjugate acid of quercetin 3-O-β-D-glucopyranoside(1−) (CHEBI:144437)
Incoming Relation(s)
Incoming Relation(s)	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	Source
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
HW2	PDBeChem
Isoquercetin	Wikipedia
LSM-5818	LINCS

Registry Numbers	Sources
Reaxys:100989	Reaxys
CAS:21637-25-2	KEGG COMPOUND
CAS:482-35-9	ChemIDplus

Citations