CHEBI:66317 - rotundifolioside J

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ChEBI Name rotundifolioside J
ChEBI ID CHEBI:66317
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 α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranosyloxy residue 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 C48H78O16
Net Charge 0
Average Mass 911.12330
Monoisotopic Mass 910.52899
InChI InChI=1S/C48H78O16/c1-21-10-16-47-20-58-48(39(47)22(21)2)17-12-27-44(7)14-13-29(43(5,6)26(44)11-15-45(27,8)46(48,9)18-28(47)50)62-41-37(34(55)31(52)24(4)60-41)64-42-38(35(56)32(53)25(19-49)61-42)63-40-36(57)33(54)30(51)23(3)59-40/h12,17,21-42,49-57H,10-11,13-16,18-20H2,1-9H3/t21-,22+,23+,24-,25-,26+,27-,28-,29+,30+,31+,32-,33-,34+,35+,36-,37-,38-,39-,40+,41+,42+,44+,45-,46+,47+,48+/m1/s1
InChIKey YYFFLJVNDZHSNP-KNFUFYRCSA-N
SMILES [H][C@]1(O[C@@H](C)[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](C)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 J (CHEBI:66317) has parent hydride ursane (CHEBI:35711)
rotundifolioside J (CHEBI:66317) has role antineoplastic agent (CHEBI:35610)
rotundifolioside J (CHEBI:66317) has role plant metabolite (CHEBI:76924)
rotundifolioside J (CHEBI:66317) is a bridged compound (CHEBI:35990)
rotundifolioside J (CHEBI:66317) is a cyclic ether (CHEBI:37407)
rotundifolioside J (CHEBI:66317) is a hexacyclic triterpenoid (CHEBI:70994)
rotundifolioside J (CHEBI:66317) is a trisaccharide derivative (CHEBI:63571)
rotundifolioside J (CHEBI:66317) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(3β,16α)-16-hydroxy-13,28-epoxyurs-11-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-6-deoxy-β-D-galactopyranoside
Synonym Source
13β,28-epoxy-16α-hydroxyurs-11-en-3β-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside ChEBI
Registry Number Type Source
9468714 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
12672986 PubMed citation Europe PMC
Last Modified
20 January 2014