3-O-[beta-D-glucopyranosyl]-28-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]asiatic acid (CHEBI:68379)

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CHEBI:68379 - 3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]asiatic acid

ChEBI ID	CHEBI:68379
ChEBI Name	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]asiatic acid
Stars
ASCII Name	3-O-[beta-D-glucopyranosyl]-28-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]asiatic acid
Definition	A triterpenoid saponin that is asiatic acid attached to a a β-D-glucopyranosyl residue at position 3 and a α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl residue at position 28. Isolated from the methanolic extract of the leaves of Symplocos lancifolia, it exhibits antibacterial activity.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C48H78O19
Net Charge	0
Average Mass	959.133
Monoisotopic Mass	958.51373
SMILES	[H][C@@]1(O[C@H]2[C@H](OC(=O)[C@]34CC[C@@H](C)[C@H](C)[C@@]3([H])C3=CC[C@]5([H])[C@@]6(C)C[C@@H](O)[C@H](O[C@]7([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@@](C)(CO)[C@]6([H])CC[C@@]5(C)[C@]3(C)CC4)O[C@H](CO)[C@@H](O)[C@@H]2O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
InChI	InChI=1S/C48H78O19/c1-20-10-13-48(43(61)67-42-38(35(58)32(55)26(18-50)64-42)65-40-36(59)33(56)30(53)22(3)62-40)15-14-46(6)23(29(48)21(20)2)8-9-28-44(4)16-24(52)39(45(5,19-51)27(44)11-12-47(28,46)7)66-41-37(60)34(57)31(54)25(17-49)63-41/h8,20-22,24-42,49-60H,9-19H2,1-7H3/t20-,21+,22+,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	QGCLLCJIKJBHAU-OFUNTZFBSA-N

Species of Metabolite	Component	Source	Comments
Symplocos lancifolia (ncbitaxon:239704)	leaf (BTO:0000713)	PubMed (21288041)	Dried, powdered leaves extracted with boiling 80% methanol

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.

ChEBI Ontology

Outgoing Relation(s)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]asiatic acid (CHEBI:68379) has functional parent asiatic acid (CHEBI:2873)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]asiatic acid (CHEBI:68379) has parent hydride ursane (CHEBI:35711)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]asiatic acid (CHEBI:68379) has role plant metabolite (CHEBI:76924)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]asiatic acid (CHEBI:68379) is a pentacyclic triterpenoid (CHEBI:25872)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]asiatic acid (CHEBI:68379) is a triterpenoid saponin (CHEBI:61778)

IUPAC Name
2-O-(6-deoxy-α-L-mannopyranosyl)-1-O-[(2α,3β)-3-(β-D-glucopyranosyloxy)-2,23-dihydroxy-28-oxours-12-en-28-yl]-β-D-glucopyranose

Registry Numbers	Sources
Reaxys:21306694	Reaxys

Citations