CHEBI:68378 - 3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid

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ChEBI Name 3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid
ChEBI ID CHEBI:68378
ChEBI ASCII Name 3-O-[beta-D-glucopyranosyl]-28-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]arjunolic acid
Definition A triterpenoid saponin that is arjunolic 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. 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 C48H78O19
Net Charge 0
Average Mass 959.12150
Monoisotopic Mass 958.51373
InChI InChI=1S/C48H78O19/c1-21-29(53)32(56)35(59)39(62-21)65-37-34(58)31(55)26(19-50)64-41(37)67-42(61)48-14-12-43(2,3)16-23(48)22-8-9-28-44(4)17-24(52)38(66-40-36(60)33(57)30(54)25(18-49)63-40)45(5,20-51)27(44)10-11-47(28,7)46(22,6)13-15-48/h8,21,23-41,49-60H,9-20H2,1-7H3/t21-,23-,24+,25+,26+,27+,28+,29-,30+,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,44-,45-,46+,47+,48-/m0/s1
InChIKey IYMDTUUDLAHXGD-HADMNRPSSA-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)(CO)[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.
(via 3-O-[beta-D-glucopyranosyl]-28-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]arjunolic acid )
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
(via 3-O-[beta-D-glucopyranosyl]-28-O-[alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl]arjunolic acid )
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]arjunolic acid (CHEBI:68378) has functional parent arjunolic acid (CHEBI:68381)
3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid (CHEBI:68378) has role antibacterial agent (CHEBI:33282)
3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid (CHEBI:68378) has role plant metabolite (CHEBI:76924)
3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid (CHEBI:68378) is a pentacyclic triterpenoid (CHEBI:25872)
3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]arjunolic acid (CHEBI:68378) 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-oxoolean-12-en-28-yl]-β-D-glucopyranose
Registry Number Type Source
21306693 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21288041 PubMed citation Europe PMC
Last Modified
20 January 2014