3-O-[beta-D-glucopyranosyl]-28-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]maslinic acid (CHEBI:68377)

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CHEBI:68377 - 3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]maslinic acid

ChEBI ID	CHEBI:68377
ChEBI Name	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]maslinic acid
Stars
ASCII Name	3-O-[beta-D-glucopyranosyl]-28-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]maslinic acid
Definition	A triterpenoid saponin that is maslinic acid attached to a β-D-glucopyranosyl residue at position 3 and a α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl residue at position 28 via a glycosidic linkage. Isolated from the methanolic extract of the leaves of Symplocos lancifolia, it exhibits antibacterial activity.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C48H78O18
Net Charge	0
Average Mass	943.134
Monoisotopic Mass	942.51882
SMILES	[H][C@@]1(O[C@H]2[C@H](OC(=O)[C@]34CCC(C)(C)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)(C)[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/C48H78O18/c1-21-29(52)32(55)35(58)39(61-21)64-37-34(57)31(54)26(20-50)63-41(37)66-42(60)48-15-13-43(2,3)17-23(48)22-9-10-28-45(6)18-24(51)38(65-40-36(59)33(56)30(53)25(19-49)62-40)44(4,5)27(45)11-12-47(28,8)46(22,7)14-16-48/h9,21,23-41,49-59H,10-20H2,1-8H3/t21-,23-,24+,25+,26+,27-,28+,29-,30+,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,45-,46+,47+,48-/m0/s1
InChIKey	IKQKYNWOONQHQK-DVSNLDMXSA-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:

antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria.

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]maslinic acid (CHEBI:68377) has functional parent maslinic acid (CHEBI:66682)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]maslinic acid (CHEBI:68377) has role antibacterial agent (CHEBI:33282)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]maslinic acid (CHEBI:68377) has role plant metabolite (CHEBI:76924)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]maslinic acid (CHEBI:68377) is a pentacyclic triterpenoid (CHEBI:25872)
	3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]maslinic acid (CHEBI:68377) is a triterpenoid saponin (CHEBI:61778)

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

Registry Numbers	Sources
Reaxys:21306692	Reaxys

Citations