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5-galloylquercetin-3-O-alpha-L-arabinofuranoside
A quercetin O-glucoside in which quercetin is attached to a alpha-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.


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03. Biological Effects of Specific Chemicals: antimicrobial agent [CHEBI:33281] > antimicrobial drug [CHEBI:36043] > antiprotozoal drug [CHEBI:35820] > antiplasmodial drug [CHEBI:64915] > 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 antimicrobial agent [CHEBI:33281] (927) 
 antimicrobial drug [CHEBI:36043] (169) 
 antiprotozoal drug [CHEBI:35820] (168) 
 antiplasmodial drug [CHEBI:64915] (28) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxyflavone [CHEBI:24698] (107) 
 trihydroxyflavone [CHEBI:27116] (39) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxyflavone [CHEBI:24698] (107) 
 trihydroxyflavone [CHEBI:27116] (39) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 glycosyl compound [CHEBI:63161] (1006) 
 glycoside [CHEBI:24400] (633) 
 pentoside [CHEBI:35312] (17) 
 arabinoside [CHEBI:22601] (13) 
 alpha-L-arabinoside [CHEBI:35376] (6) 
 alpha-L-arabinofuranoside [CHEBI:37572] (2) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 glycosyloxyflavone [CHEBI:50018] (49) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 carbohydrate derivative [CHEBI:63299] (2582) 
 monosaccharide derivative [CHEBI:63367] (720) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 flavonoids [CHEBI:72544] (433) 
 flavonoid [CHEBI:47916] (301) 
 flavones [CHEBI:24043] (130) 
 hydroxyflavone [CHEBI:24698] (107) 
 trihydroxyflavone [CHEBI:27116] (39) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 glycosyloxyflavone [CHEBI:50018] (49) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 glycosyl compound [CHEBI:63161] (1006) 
 glycoside [CHEBI:24400] (633) 
 pentoside [CHEBI:35312] (17) 
 arabinoside [CHEBI:22601] (13) 
 alpha-L-arabinoside [CHEBI:35376] (6) 
 alpha-L-arabinofuranoside [CHEBI:37572] (2) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 glycosyloxyflavone [CHEBI:50018] (49) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 carbohydrate derivative [CHEBI:63299] (2582) 
 monosaccharide derivative [CHEBI:63367] (720) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 glycosyl compound [CHEBI:63161] (1006) 
 glycoside [CHEBI:24400] (633) 
 pentoside [CHEBI:35312] (17) 
 arabinoside [CHEBI:22601] (13) 
 alpha-L-arabinoside [CHEBI:35376] (6) 
 alpha-L-arabinofuranoside [CHEBI:37572] (2) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 glycosyloxyflavone [CHEBI:50018] (49) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 carbohydrate derivative [CHEBI:63299] (2582) 
 monosaccharide derivative [CHEBI:63367] (720) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxyflavone [CHEBI:24698] (107) 
 trihydroxyflavone [CHEBI:27116] (39) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 flavonoids [CHEBI:72544] (433) 
 flavonoid [CHEBI:47916] (301) 
 flavones [CHEBI:24043] (130) 
 hydroxyflavone [CHEBI:24698] (107) 
 trihydroxyflavone [CHEBI:27116] (39) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 glycosyloxyflavone [CHEBI:50018] (49) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 hydroxyflavone [CHEBI:24698] (107) 
 trihydroxyflavone [CHEBI:27116] (39) 
 5-galloylquercetin-3-O-alpha-L-arabinofuranoside [CHEBI:65942] (1)
ChEBI Compound Accession Identifier  [CHEBI:65942]
ChEBI Compound Description  A quercetin O-glucoside in which quercetin is attached to a alpha-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.
ChEBI Compound Identification Number  65942
ChEBI InChI Value  InChI=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
ChEBI InChIKey Value  GUMSRJAIAPTKAF-CSEOLDMBSA-N
ChEBI Compound Name  5-galloylquercetin-3-O-alpha-L-arabinofuranoside
ChEBI SMILES Value  OC[C@@H]1O[C@@H](Oc2c(oc3cc(O)cc(C(=O)c4cc(O)c(O)c(O)c4)c3c2=O)-c2ccc(O)c(O)c2)[C@H](O)[C@H]1O
ChEBI Substance ID  160710093
ChEBI URL  ChEBI:65942
ChemSpider ID  28532997
Ontomatica Chemical Accession Key (OnChAKey)  GUMSRJAIAPTKAF_CSEOLDMBSA_N_000_000000
PubChem Compound ID  70697845