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rotundifolioside I

Go to external page http://purl.obolibrary.org/obo/CHEBI_66316

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-yl beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranosyl-(1->2)-beta-D-fucopyranosyloxy residue 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 I

Synonyms
  • (3beta,16alpha)-16-hydroxy-13,28-epoxyurs-11-en-3-yl beta-D-xylopyranosyl-(1->2)-beta-D-glucopyranosyl-(1->2)-6-deoxy-beta-D-galactopyranoside
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)-6-deoxy-beta-D-galactopyranoside [ IUPAC ]

charge

0

formula

C47H76O16

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-fucopyranoside

id

CHEBI:66316

inchi

InChI=1S/C47H76O16/c1-21-9-15-46-20-58-47(38(46)22(21)2)16-11-27-43(6)13-12-29(42(4,5)26(43)10-14-44(27,7)45(47,8)17-28(46)50)61-40-36(33(54)30(51)23(3)59-40)63-41-37(34(55)32(53)25(18-48)60-41)62-39-35(56)31(52)24(49)19-57-39/h11,16,21-41,48-56H,9-10,12-15,17-20H2,1-8H3/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

RHHWBSQGVOHKJH-ZKLLPSJOSA-N

mass

897.09670

monoisotopicmass

896.51334

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](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