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

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ChEBI Name 3-O-[β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl]asiatic acid
ChEBI ID CHEBI:68379
ChEBI 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.
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/c1-20-10-13-48(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
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@]12CC[C@@H](C)[C@H](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.
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]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 Number Type Source
21306694 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21288041 PubMed citation Europe PMC
Last Modified
20 January 2014