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CHEBI:66582 - litseaefoloside C

ChEBI IDCHEBI:66582
ChEBI Namelitseaefoloside C
Stars
DefinitionAn O-acyl carbohydrate consisting of glucose attached to 2-hydroxy-4-vanilloyloxymethylphenyl and trans-caffeoyl group at positions 1 and 6 respectively. Isolated from stems of Ilex latifolia, it exhibits inhibitory activity against α-glucosidase and lipase.
Last Modified22 March 2013
DownloadsMolfile
FormulaC30H30O14
Net Charge0
Average Mass614.556
Monoisotopic Mass614.16356
SMILESCOc1cc(C(=O)OCc2ccc(O[C@@H]3O[C@H](COC(=O)/C=C/c4ccc(O)c(O)c4)[C@@H](O)[C@H](O)[C@H]3O)c(O)c2)ccc1O
InChIInChI=1S/C30H30O14/c1-40-23-12-17(5-7-19(23)32)29(39)42-13-16-3-8-22(21(34)11-16)43-30-28(38)27(37)26(36)24(44-30)14-41-25(35)9-4-15-2-6-18(31)20(33)10-15/h2-12,24,26-28,30-34,36-38H,13-14H2,1H3/b9-4+/t24-,26-,27+,28-,30-/m1/s1
InChIKeyIMVLKRZWKQBCNJ-ZAHDVKFQSA-N
Species of MetaboliteComponentSourceComments
Ilex latifolia (ncbitaxon:53205) stem (BTO:0001300) PubMed (16252920)
Roles Classification
Biological Roles:
EC 3.2.1.20 (alpha-glucosidase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of α-glucosidase (EC 3.2.1.20).
EC 3.1.1.3 (triacylglycerol lipase) inhibitor  Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of triacylglycerol lipase (EC 3.1.1.3).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
litseaefoloside C (CHEBI:66582) has functional parent trans-caffeic acid (CHEBI:16433)
litseaefoloside C (CHEBI:66582) has functional parent vanillic acid (CHEBI:30816)
litseaefoloside C (CHEBI:66582) has role EC 3.1.1.3 (triacylglycerol lipase) inhibitor (CHEBI:65001)
litseaefoloside C (CHEBI:66582) has role EC 3.2.1.20 (α-glucosidase) inhibitor (CHEBI:67239)
litseaefoloside C (CHEBI:66582) has role metabolite (CHEBI:25212)
litseaefoloside C (CHEBI:66582) is a O-acyl carbohydrate (CHEBI:52782)
litseaefoloside C (CHEBI:66582) is a cinnamate ester (CHEBI:36087)
litseaefoloside C (CHEBI:66582) is a polyphenol (CHEBI:26195)
litseaefoloside C (CHEBI:66582) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
4-({6-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-β-D-glucopyranosyl}oxy)-3-hydroxybenzyl 4-hydroxy-3-methoxybenzoate
Synonyms  Source
3-hydroxy-4-O-β-D-(6-O-caffeoylglucopyranosyl)benzyl vanilloateChEBI
[4-[(2S,3R,4S,5S,6R)-6-[[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxyphenyl]methyl4-hydroxy-3-methoxybenzoateChEBI
Registry NumbersSources
Reaxys:18614352Reaxys
Citations