CHEBI:65402 - amburoside A

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ChEBI Name amburoside A
ChEBI ID CHEBI:65402
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H22O10
Net Charge 0
Average Mass 422.38270
Monoisotopic Mass 422.12130
InChI InChI=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
InChIKey LRFIKYDSTHZRKW-BFMVXSJESA-N
SMILES OC[C@H]1O[C@@H](Oc2ccc(COC(=O)c3ccc(O)c(O)c3)cc2)[C@H](O)[C@@H](O)[C@@H]1O
Metabolite of Species Details
Amburana cearensis (NCBI:txid149628) Found in trunk bark (BTO:0001494). See: DOI
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): 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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): 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.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
hepatoprotective agent
Any compound that is able to prevent damage to the liver.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
amburoside A (CHEBI:65402) is a benzoate ester (CHEBI:36054)
amburoside A (CHEBI:65402) is a catechols (CHEBI:33566)
IUPAC Name
4-(β-D-glucopyranosyloxy)benzyl 3,4-dihydroxybenzoate
Synonym Source
4-(O-β-D-glucopyranosyl)benzyl protocatechoate ChEBI
Registry Number Type Source
6896550 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
14577630 PubMed citation Europe PMC
16039060 PubMed citation Europe PMC
18404596 PubMed citation Europe PMC
19053991 PubMed citation Europe PMC
20638258 PubMed citation Europe PMC
Last Modified
01 November 2012