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

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ChEBI Name 4'-O-demethylknipholone-4'-O-β-D-glucopyranoside
ChEBI ID CHEBI:65741
ChEBI ASCII Name 4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C29H26O13
Net Charge 0
Average Mass 582.510
Monoisotopic Mass 582.13734
InChI InChI=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
InChIKey AOJYFODHRHWWEN-GQUXZSRASA-N
SMILES O([C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C2=CC(=C(C=3C4=C(C(=O)C5=C(C=CC=C5C4=O)O)C(=CC3C)O)C(=C2C(=O)C)O)O
Metabolite of Species Details
Bulbine frutescens (NCBI:txid210954) Found in root (BTO:0001188). 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.
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.
trypanocidal drug
A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
Application(s): 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.
trypanocidal drug
A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
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)
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 Number Type Source
10140237 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
12193014 PubMed citation Europe PMC
Last Modified
14 June 2016