CHEBI:66314 - rotundifolioside A

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ChEBI Name rotundifolioside A
ChEBI ID CHEBI:66314
Definition A triterpenoid saponin that consists of urs-11-ene substituted by an epoxy group across positions 13 and 28, a hydroxy group at position 16 and a β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyloxy group at position 3 (the 3β,16α stereoisomer). Isolated from the fruits of Bupleurum rotundifolium, it exhibits antiproliferative activity against cancer cells.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C47H76O17
Net Charge 0
Average Mass 913.09610
Monoisotopic Mass 912.50825
InChI InChI=1S/C47H76O17/c1-21-8-14-46-20-59-47(38(46)22(21)2)15-10-27-43(5)12-11-29(42(3,4)26(43)9-13-44(27,6)45(47,7)16-28(46)51)62-40-36(33(55)31(53)24(17-48)60-40)64-41-37(34(56)32(54)25(18-49)61-41)63-39-35(57)30(52)23(50)19-58-39/h10,15,21-41,48-57H,8-9,11-14,16-20H2,1-7H3/t21-,22+,23-,24-,25-,26+,27-,28-,29+,30+,31-,32-,33+,34+,35-,36-,37-,38-,39+,40+,41+,43+,44-,45+,46+,47+/m1/s1
InChIKey OERYSJKYOLNHAD-NCFQBMSRSA-N
SMILES [H][C@]1(OC[C@@H](O)[C@H](O)[C@H]1O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@]1([H])O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@]1([H])O[C@H]1CC[C@@]2(C)[C@@]([H])(CC[C@]3(C)[C@]2([H])C=C[C@]24OC[C@@]5(CC[C@@H](C)[C@H](C)[C@@]25[H])[C@H](O)C[C@@]34C)C1(C)C
Metabolite of Species Details
Bupleurum rotundifolium (NCBI:txid90446) Found in fruit (BTO:0000486). See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing rotundifolioside A (CHEBI:66314) has parent hydride ursane (CHEBI:35711)
rotundifolioside A (CHEBI:66314) has role antineoplastic agent (CHEBI:35610)
rotundifolioside A (CHEBI:66314) has role plant metabolite (CHEBI:76924)
rotundifolioside A (CHEBI:66314) is a bridged compound (CHEBI:35990)
rotundifolioside A (CHEBI:66314) is a cyclic ether (CHEBI:37407)
rotundifolioside A (CHEBI:66314) is a hexacyclic triterpenoid (CHEBI:70994)
rotundifolioside A (CHEBI:66314) is a trisaccharide derivative (CHEBI:63571)
rotundifolioside A (CHEBI:66314) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(3β,16α)-16-hydroxy-13,28-epoxyurs-11-en-3-yl β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside
Synonym Source
13β,28-epoxy-16α-hydroxyurs-11-en-3β-yl β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside ChEBI
Citation Waiting for Citations Type Source
12672986 PubMed citation Europe PMC
Last Modified
20 January 2014