CHEBI:67931 - petiolaroside

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ChEBI Name petiolaroside
ChEBI ID CHEBI:67931
Definition A quercetin O-glucoside that is quercetin attached to β-D-glucopyranosyl residue at position 3 and a α-L-rhamnopyranosyl residue at position 7 via glycosidic linkages. Isolated from the aerial parts of Delphinium staphisagria, it exhibits trypanocidal activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H30O16
Net Charge 0
Average Mass 610.51750
Monoisotopic Mass 610.15338
InChI InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(39-8)40-10-5-13(31)16-14(6-10)41-24(9-2-3-11(29)12(30)4-9)25(19(16)34)43-27-23(38)21(36)18(33)15(7-28)42-27/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26-,27-/m0/s1
InChIKey OTUCXMIQUNROBJ-JFNZIVIESA-N
SMILES C[C@@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(-c2ccc(O)c(O)c2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c3=O)[C@H](O)[C@H](O)[C@H]1O
Metabolite of Species Details
Delphinium staphisagria (NCBI:txid104301) Found in aerial part (BTO:0001658). 80% ethanolic extract of chopped fresh plant See: PubMed
Roles Classification
Biological Role(s): trypanocidal drug
A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): 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 petiolaroside (CHEBI:67931) has functional parent α-L-rhamnopyranose (CHEBI:27907)
petiolaroside (CHEBI:67931) has role plant metabolite (CHEBI:76924)
petiolaroside (CHEBI:67931) has role trypanocidal drug (CHEBI:36335)
petiolaroside (CHEBI:67931) is a β-D-glucoside (CHEBI:22798)
petiolaroside (CHEBI:67931) is a quercetin O-glucoside (CHEBI:64621)
petiolaroside (CHEBI:67931) is a trihydroxyflavone (CHEBI:27116)
petiolaroside (CHEBI:67931) is conjugate acid of petiolaroside(1−) (CHEBI:144436)
Incoming 2ʼʼ-acetylpetiolaroside (CHEBI:67932) has functional parent petiolaroside (CHEBI:67931)
petiolaroside decaacetate (CHEBI:67933) has functional parent petiolaroside (CHEBI:67931)
petiolaroside(1−) (CHEBI:144436) is conjugate base of petiolaroside (CHEBI:67931)
IUPAC Name
7-[(6-deoxy-α-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-3-yl β-D-glucopyranoside
Synonyms Sources
7-((6-deoxy-α-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one ChemIDplus
quercetin-3-O-β-D-glucopyranoside-7-O-α-L-rhamnopyranoside ChEBI
vincetoxicoside A ChemIDplus
Registry Numbers Types Sources
1339876 Reaxys Registry Number Reaxys
18016-58-5 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
21466157 PubMed citation Europe PMC
Last Modified
09 January 2014