CHEBI:70146 - robustaside D

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ChEBI Name robustaside D
ChEBI ID CHEBI:70146
Definition A β-D-glucoside in which the anomeric position is substituted by a 4-hydroxyphenoxy residue and at position 6 by [(2E)-3-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)prop-2-enoyl]oxy residue. Isolated from Grevillea, it exhibits antimalarial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H22O10
Net Charge 0
Average Mass 434.39340
Monoisotopic Mass 434.12130
InChI InChI=1S/C21H22O10/c22-12-1-3-14(4-2-12)30-20-19(27)18(26)17(25)15(31-20)11-29-16(24)7-10-21(28)8-5-13(23)6-9-21/h1-10,15,17-20,22,25-28H,11H2/b10-7+/t15-,17-,18+,19-,20-/m1/s1
InChIKey KQIQKULTIAJZKL-VHFDLOJPSA-N
SMILES O[C@@H]1[C@@H](COC(=O)\C=C\C2(O)C=CC(=O)C=C2)O[C@@H](Oc2ccc(O)cc2)[C@H](O)[C@H]1O
Metabolite of Species Details
Grevillea (NCBI:txid83716) Found in twig (BTO:0001411). Combined methanolic extract of freeze-dried, ground plant material See: PubMed
Grevillea (NCBI:txid83716) Found in leaf (BTO:0000713). Combined methanolic extract of freeze-dried, ground plant material See: PubMed
Roles Classification
Biological Role(s): 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.
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.
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ChEBI Ontology
Outgoing robustaside D (CHEBI:70146) has role antimalarial (CHEBI:38068)
robustaside D (CHEBI:70146) has role metabolite (CHEBI:25212)
robustaside D (CHEBI:70146) is a β-D-glucoside (CHEBI:22798)
robustaside D (CHEBI:70146) is a cyclic ketone (CHEBI:3992)
robustaside D (CHEBI:70146) is a enoate ester (CHEBI:51702)
robustaside D (CHEBI:70146) is a monosaccharide derivative (CHEBI:63367)
robustaside D (CHEBI:70146) is a phenols (CHEBI:33853)
IUPAC Name
4-hydroxyphenyl 6-O-[(2E)-3-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)prop-2-enoyl]-β-D-glucopyranoside
Registry Number Type Source
8654721 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21155593 PubMed citation Europe PMC
Last Modified
26 July 2013