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CHEBI:66582 - litseaefoloside C

Default Structure
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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
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).
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