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CHEBI:65741 - 4'-O-demethylknipholone-4'-O-β-D-glucopyranoside

ChEBI IDCHEBI:65741
ChEBI Name4'-O-demethylknipholone-4'-O-β-D-glucopyranoside
Stars
ASCII Name4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside
DefinitionAn anthraquinone that is knipholone in which the O-methyl group is replaced by a β-D-glucopyranosyl group. It is isolated from the roots of Bulbine frutescens and exhibits trypanocidal and antiplasmodial activities.
Last Modified14 June 2016
DownloadsMolfile
FormulaC29H26O13
Net Charge0
Average Mass582.514
Monoisotopic Mass582.13734
SMILESCC(=O)c1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc(O)c(-c2c(C)cc(O)c3c2C(=O)c2cccc(O)c2C3=O)c1O
InChIInChI=1S/C29H26O13/c1-9-6-13(33)21-22(23(35)11-4-3-5-12(32)19(11)26(21)38)17(9)20-14(34)7-15(18(10(2)31)25(20)37)41-29-28(40)27(39)24(36)16(8-30)42-29/h3-7,16,24,27-30,32-34,36-37,39-40H,8H2,1-2H3/t16-,24-,27+,28-,29-/m1/s1
InChIKeyAOJYFODHRHWWEN-GQUXZSRASA-N
Species of MetaboliteComponentSourceComments
Bulbine frutescens (ncbitaxon:210954) root (BTO:0001188) PubMed (12193014)
Roles Classification
Biological Roles:
trypanocidal drug  A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
trypanocidal drug  A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
ChEBI Ontology
Outgoing Relation(s)
4'-O-demethylknipholone-4'-O-β-D-glucopyranoside (CHEBI:65741) has functional parent knipholone (CHEBI:6141)
4'-O-demethylknipholone-4'-O-β-D-glucopyranoside (CHEBI:65741) has role antiplasmodial drug (CHEBI:64915)
4'-O-demethylknipholone-4'-O-β-D-glucopyranoside (CHEBI:65741) has role metabolite (CHEBI:25212)
4'-O-demethylknipholone-4'-O-β-D-glucopyranoside (CHEBI:65741) has role trypanocidal drug (CHEBI:36335)
4'-O-demethylknipholone-4'-O-β-D-glucopyranoside (CHEBI:65741) is a aromatic ketone (CHEBI:76224)
4'-O-demethylknipholone-4'-O-β-D-glucopyranoside (CHEBI:65741) is a dihydroxyanthraquinone (CHEBI:37484)
4'-O-demethylknipholone-4'-O-β-D-glucopyranoside (CHEBI:65741) is a methyl ketone (CHEBI:51867)
4'-O-demethylknipholone-4'-O-β-D-glucopyranoside (CHEBI:65741) is a polyphenol (CHEBI:26195)
4'-O-demethylknipholone-4'-O-β-D-glucopyranoside (CHEBI:65741) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
2-acetyl-4-(4,5-dihydroxy-2-methyl-9,10-dioxo-9,10-dihydroanthracen-1-yl)-3,5-dihydroxyphenyl β-D-glucopyranoside
Registry NumbersSources
Reaxys:10140237Reaxys
Citations