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CHEBI:70146 - robustaside D

ChEBI IDCHEBI:70146
ChEBI Namerobustaside D
Stars
DefinitionA 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.
Last Modified26 July 2013
DownloadsMolfile
FormulaC21H22O10
Net Charge0
Average Mass434.397
Monoisotopic Mass434.12130
SMILESO=C1C=CC(O)(/C=C/C(=O)OC[C@H]2O[C@@H](Oc3ccc(O)cc3)[C@H](O)[C@@H](O)[C@@H]2O)C=C1
InChIInChI=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
InChIKeyKQIQKULTIAJZKL-VHFDLOJPSA-N
Species of MetaboliteComponentSourceComments
Grevillea (ncbitaxon:83716)
leaf (BTO:0000713) PubMed (21155593) Combined methanolic extract of freeze-dried, ground plant material
twig (BTO:0001411) PubMed (21155593) Combined methanolic extract of freeze-dried, ground plant material
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.
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:
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)
robustaside D (CHEBI:70146) has role antimalarial (CHEBI:38068)
robustaside D (CHEBI:70146) has role metabolite (CHEBI:25212)
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)
robustaside D (CHEBI:70146) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
4-hydroxyphenyl 6-O-[(2E)-3-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)prop-2-enoyl]-β-D-glucopyranoside
Registry NumbersSources
Reaxys:8654721Reaxys
Citations