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CHEBI:65402 - amburoside A

Default Structure
ChEBI IDCHEBI:65402
ChEBI Nameamburoside A
Stars
DefinitionA β-D-glucoside in which a β-D-glucopyranosyl residue is attached at position 4 of 4-hydroxybenzyl 3,4-dihydroxybenzoate via a glycosidic linkage. It is isolated from the trunk barks of Amburana cearensis and exhibits antimalarial, neuroprotective, hepatoprotective and antioxidant activities.
Last Modified1 November 2012
DownloadsMolfile
FormulaC20H22O10
Net Charge0
Average Mass422.386
Monoisotopic Mass422.12130
SMILESO=C(OCc1ccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1)c1ccc(O)c(O)c1
InChIInChI=1S/C20H22O10/c21-8-15-16(24)17(25)18(26)20(30-15)29-12-4-1-10(2-5-12)9-28-19(27)11-3-6-13(22)14(23)7-11/h1-7,15-18,20-26H,8-9H2/t15-,16-,17+,18-,20-/m1/s1
InChIKeyLRFIKYDSTHZRKW-BFMVXSJESA-N
Species of MetaboliteComponentSourceComments
Amburana cearensis (ncbitaxon:149628) trunk bark (BTO:0001494) DOI (10.1016/S0031-9422(98)00497-X)
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Applications:
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
ChEBI Ontology
Outgoing Relation(s)
amburoside A (CHEBI:65402) has role antimalarial (CHEBI:38068)
amburoside A (CHEBI:65402) has role antioxidant (CHEBI:22586)
amburoside A (CHEBI:65402) has role hepatoprotective agent (CHEBI:62868)
amburoside A (CHEBI:65402) has role metabolite (CHEBI:25212)
amburoside A (CHEBI:65402) has role neuroprotective agent (CHEBI:63726)
amburoside A (CHEBI:65402) is a benzoate ester (CHEBI:36054)
amburoside A (CHEBI:65402) is a catechols (CHEBI:33566)
amburoside A (CHEBI:65402) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
4-(β-D-glucopyranosyloxy)benzyl 3,4-dihydroxybenzoate
Synonym  Source
4-(O-β-D-glucopyranosyl)benzyl protocatechoateChEBI
Registry NumbersSources
Reaxys:6896550Reaxys
Citations