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CHEBI:66315 - rotundifolioside H

ChEBI IDCHEBI:66315
ChEBI Namerotundifolioside H
Stars
DefinitionA triterpenoid saponin that consists of urs-11-ene substituted by an epoxy group across positions 13 and 28, a hydroxy groups at position 16 and 23 and a β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranosyloxy group at position 3 (the 3β,16α stereoisomer). Isolated from the fruits of Bupleurum rotundifolium, it exhibits antiproliferative activity against cancer cells.
Last Modified20 January 2014
DownloadsMolfile
FormulaC47H76O17
Net Charge0
Average Mass913.108
Monoisotopic Mass912.50825
SMILES[H][C@@]1(O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@@]2([H])O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](C)O[C@@]2([H])O[C@H]2CC[C@]3(C)[C@@]4([H])C=C[C@]56OC[C@@]7(CC[C@@H](C)[C@H](C)[C@]75[H])[C@H](O)C[C@@]6(C)[C@]4(C)CC[C@@]3([H])[C@]2(C)CO)OC[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C47H76O17/c1-21-8-14-46-20-59-47(38(46)22(21)2)15-10-27-42(4)12-11-29(43(5,19-49)26(42)9-13-44(27,6)45(47,7)16-28(46)51)62-40-36(33(55)30(52)23(3)60-40)64-41-37(34(56)32(54)25(17-48)61-41)63-39-35(57)31(53)24(50)18-58-39/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+,42+,43+,44-,45+,46+,47+/m1/s1
InChIKeyGIGMOKRQIQCYNY-JFEKQVAJSA-N
Species of MetaboliteComponentSourceComments
Bupleurum rotundifolium (ncbitaxon:90446) fruit (BTO:0000486) PubMed (12672986)
Roles Classification
Biological Roles:
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
rotundifolioside H (CHEBI:66315) has parent hydride ursane (CHEBI:35711)
rotundifolioside H (CHEBI:66315) has role antineoplastic agent (CHEBI:35610)
rotundifolioside H (CHEBI:66315) has role plant metabolite (CHEBI:76924)
rotundifolioside H (CHEBI:66315) is a bridged compound (CHEBI:35990)
rotundifolioside H (CHEBI:66315) is a cyclic ether (CHEBI:37407)
rotundifolioside H (CHEBI:66315) is a hexacyclic triterpenoid (CHEBI:70994)
rotundifolioside H (CHEBI:66315) is a trisaccharide derivative (CHEBI:63571)
rotundifolioside H (CHEBI:66315) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name 
(3β,16α)-16,23-dihydroxy-13,28-epoxyurs-11-en-3-yl β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-6-deoxy-β-D-galactopyranoside
Synonym  Source
13β,28-epoxy-16α,23-dihydroxyurs-11-en-3β-yl β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranosideChEBI
Citations