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CHEBI:65942 - 5-galloylquercetin-3-O-α-L-arabinofuranoside

ChEBI IDCHEBI:65942
ChEBI Name5-galloylquercetin-3-O-α-L-arabinofuranoside
Stars
ASCII Name5-galloylquercetin-3-O-alpha-L-arabinofuranoside
DefinitionA quercetin O-glucoside in which quercetin is attached to a α-L-arabinofuranosyl group at position 3 via a glycosidic linkage while the hydroxy group at position 5 is replaced by a galloyl group. Isolated from the young leaves of Calycolpus warscewiczianus, it exhibits activity against a chloroquine-resistant strain of Plasmodium falciparum.
Last Modified21 February 2013
DownloadsMolfile
FormulaC27H22O14
Net Charge0
Average Mass570.459
Monoisotopic Mass570.10096
SMILESO=C(c1cc(O)c(O)c(O)c1)c1cc(O)cc2oc(-c3ccc(O)c(O)c3)c(O[C@@H]3O[C@@H](CO)[C@H](O)[C@H]3O)c(=O)c12
InChIInChI=1S/C27H22O14/c28-8-18-22(36)24(38)27(40-18)41-26-23(37)19-12(20(34)10-4-15(32)21(35)16(33)5-10)6-11(29)7-17(19)39-25(26)9-1-2-13(30)14(31)3-9/h1-7,18,22,24,27-33,35-36,38H,8H2/t18-,22-,24+,27-/m0/s1
InChIKeyGUMSRJAIAPTKAF-CSEOLDMBSA-N
Species of MetaboliteComponentSourceComments
Calycolpus warscewiczianus (IPNI:591496-1) leaf (BTO:0000713) PubMed (16724851) young leaves
Roles Classification
Biological Roles:
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
ChEBI Ontology
Outgoing Relation(s)
5-galloylquercetin-3-O-α-L-arabinofuranoside (CHEBI:65942) has functional parent gallic acid (CHEBI:30778)
5-galloylquercetin-3-O-α-L-arabinofuranoside (CHEBI:65942) has role antiplasmodial drug (CHEBI:64915)
5-galloylquercetin-3-O-α-L-arabinofuranoside (CHEBI:65942) has role metabolite (CHEBI:25212)
5-galloylquercetin-3-O-α-L-arabinofuranoside (CHEBI:65942) is a glycosyloxyflavone (CHEBI:50018)
5-galloylquercetin-3-O-α-L-arabinofuranoside (CHEBI:65942) is a monosaccharide derivative (CHEBI:63367)
5-galloylquercetin-3-O-α-L-arabinofuranoside (CHEBI:65942) is a trihydroxyflavone (CHEBI:27116)
5-galloylquercetin-3-O-α-L-arabinofuranoside (CHEBI:65942) is a α-L-arabinofuranoside (CHEBI:37572)
IUPAC Name 
2-(3,4-dihydroxyphenyl)-7-hydroxy-4-oxo-5-(3,4,5-trihydroxybenzoyl)-4H-chromen-3-yl α-L-arabinofuranoside
Citations