rotundifolioside I (CHEBI:66316)

EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66316 - rotundifolioside I

Take structure to advanced search

ChEBI ID	CHEBI:66316
ChEBI Name	rotundifolioside I
Stars
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-yl β-D-xylopyranosyl-(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.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C47H76O16
Net Charge	0
Average Mass	897.109
Monoisotopic Mass	896.51334
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])C2(C)C)OC[C@@H](O)[C@H](O)[C@H]1O
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

Species of Metabolite	Component	Source	Comments
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 I (CHEBI:66316) has parent hydride ursane (CHEBI:35711)
	rotundifolioside I (CHEBI:66316) has role antineoplastic agent (CHEBI:35610)
	rotundifolioside I (CHEBI:66316) has role plant metabolite (CHEBI:76924)
	rotundifolioside I (CHEBI:66316) is a bridged compound (CHEBI:35990)
	rotundifolioside I (CHEBI:66316) is a cyclic ether (CHEBI:37407)
	rotundifolioside I (CHEBI:66316) is a hexacyclic triterpenoid (CHEBI:70994)
	rotundifolioside I (CHEBI:66316) is a trisaccharide derivative (CHEBI:63571)
	rotundifolioside I (CHEBI:66316) 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)-6-deoxy-β-D-galactopyranoside

Synonym	Source
13β,28-epoxy-16α-hydroxyurs-11-en-3β-yl β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside	ChEBI

Registry Numbers	Sources
Reaxys:9468610	Reaxys

Citations