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rotundifolioside A

Go to external page http://purl.obolibrary.org/obo/CHEBI_66314

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 beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranosyloxy group at position 3 (the 3beta,16alpha stereoisomer). Isolated from the fruits of Bupleurum rotundifolium, it exhibits antiproliferative activity against cancer cells.

Term info

Label

rotundifolioside A

Synonyms
  • (3beta,16alpha)-16-hydroxy-13,28-epoxyurs-11-en-3-yl beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranoside
database cross reference
Subsets

3_STAR

IUPAC NAME
(3beta,16alpha)-16-hydroxy-13,28-epoxyurs-11-en-3-yl beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranoside [ IUPAC ]

charge

0

formula

C47H76O17

has obo namespace

chebi_ontology

has related synonym

13beta,28-epoxy-16alpha-hydroxyurs-11-en-3beta-yl beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranosyl-(1->2)-beta-D-glucopyranoside

id

CHEBI:66314

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

mass

913.09610

monoisotopicmass

912.50825

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