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

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ChEBI Name 3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]maslinic acid
ChEBI ID CHEBI:68377
ChEBI 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C48H78O18
Net Charge 0
Average Mass 943.12210
Monoisotopic Mass 942.51882
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
SMILES [H][C@]1(O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(=O)[C@]12CCC(C)(C)C[C@@]1([H])C1=CC[C@]3([H])[C@@]4(C)C[C@@H](O)[C@H](O[C@]5([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(C)(C)[C@]4([H])CC[C@@]3(C)[C@]1(C)CC2
Metabolite of Species Details
Symplocos lancifolia (NCBI:txid239704) Found in leaf (BTO:0000713). Dried, powdered leaves extracted with boiling 80% methanol See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
21306692 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21288041 PubMed citation Europe PMC
Last Modified
20 January 2014