CHEBI:66290 - quillaic acid α-L-Arap-(1→4)-α-L-Arap-(1→3)-β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-β-D-fucopyranosyl ester

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ChEBI Name quillaic acid α-L-Arap-(1→4)-α-L-Arap-(1→3)-β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-β-D-fucopyranosyl ester
ChEBI ID CHEBI:66290
ChEBI ASCII Name quillaic acid alpha-L-Arap-(1->4)-alpha-L-Arap-(1->3)-beta-D-Xylp-(1->4)-alpha-L-Rhap-(1->2)-beta-D-fucopyranosyl ester
Definition A triterpenoid saponin that is the pentasaccharide derivative of quillaic acid. Isolated from the roots of Gypsophila oldhamiana, it exhibits immunomodulatory activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C57H90O25
Net Charge 0
Average Mass 1175.30950
Monoisotopic Mass 1174.57712
InChI InChI=1S/C57H90O25/c1-23-34(63)37(66)45(81-49-41(70)38(67)43(24(2)77-49)79-48-42(71)44(28(60)20-74-48)80-47-40(69)36(65)29(21-75-47)78-46-39(68)35(64)27(59)19-73-46)50(76-23)82-51(72)57-16-15-52(3,4)17-26(57)25-9-10-31-53(5)13-12-32(61)54(6,22-58)30(53)11-14-55(31,7)56(25,8)18-33(57)62/h9,22-24,26-50,59-71H,10-21H2,1-8H3/t23-,24+,26+,27+,28-,29+,30-,31-,32+,33-,34+,35+,36+,37+,38+,39-,40-,41-,42-,43+,44+,45-,46+,47+,48+,49+,50+,53+,54+,55-,56-,57-/m1/s1
InChIKey OFOINNASBFYBOI-NJDMZDQFSA-N
SMILES [H][C@]1(OC[C@H](O)[C@H](O)[C@H]1O)O[C@H]1CO[C@@]([H])(O[C@H]2[C@H](O)CO[C@@]([H])(O[C@H]3[C@H](C)O[C@@]([H])(O[C@@H]4[C@@H](O)[C@@H](O)[C@@H](C)O[C@H]4OC(=O)[C@]45CCC(C)(C)C[C@@]4([H])C4=CC[C@]6([H])[C@@]7(C)CC[C@H](O)[C@@](C)(C=O)[C@]7([H])CC[C@@]6(C)[C@]4(C)C[C@H]5O)[C@H](O)[C@@H]3O)[C@@H]2O)[C@H](O)[C@H]1O
Metabolite of Species Details
Gypsophila oldhamiana (IPNI:154553-1) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
(via quillaic acid alpha-L-Arap-(1->4)-alpha-L-Arap-(1->3)-beta-D-Xylp-(1->4)-alpha-L-Rhap-(1->2)-beta-D-fucopyranosyl ester )
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via quillaic acid alpha-L-Arap-(1->4)-alpha-L-Arap-(1->3)-beta-D-Xylp-(1->4)-alpha-L-Rhap-(1->2)-beta-D-fucopyranosyl ester )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
Application(s): immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
(via quillaic acid alpha-L-Arap-(1->4)-alpha-L-Arap-(1->3)-beta-D-Xylp-(1->4)-alpha-L-Rhap-(1->2)-beta-D-fucopyranosyl ester )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing quillaic acid α-L-Arap-(1→4)-α-L-Arap-(1→3)-β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-β-D-fucopyranosyl ester (CHEBI:66290) has functional parent quillaic acid (CHEBI:8710)
quillaic acid α-L-Arap-(1→4)-α-L-Arap-(1→3)-β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-β-D-fucopyranosyl ester (CHEBI:66290) has role immunomodulator (CHEBI:50846)
quillaic acid α-L-Arap-(1→4)-α-L-Arap-(1→3)-β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-β-D-fucopyranosyl ester (CHEBI:66290) has role plant metabolite (CHEBI:76924)
quillaic acid α-L-Arap-(1→4)-α-L-Arap-(1→3)-β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-β-D-fucopyranosyl ester (CHEBI:66290) is a aldehyde (CHEBI:17478)
quillaic acid α-L-Arap-(1→4)-α-L-Arap-(1→3)-β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-β-D-fucopyranosyl ester (CHEBI:66290) is a carboxylic ester (CHEBI:33308)
quillaic acid α-L-Arap-(1→4)-α-L-Arap-(1→3)-β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-β-D-fucopyranosyl ester (CHEBI:66290) is a pentacyclic triterpenoid (CHEBI:25872)
quillaic acid α-L-Arap-(1→4)-α-L-Arap-(1→3)-β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-β-D-fucopyranosyl ester (CHEBI:66290) is a pentasaccharide derivative (CHEBI:63566)
quillaic acid α-L-Arap-(1→4)-α-L-Arap-(1→3)-β-D-Xylp-(1→4)-α-L-Rhap-(1→2)-β-D-fucopyranosyl ester (CHEBI:66290) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
α-L-arabinopyranosyl-(1→4)-α-L-arabinopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-6-deoxy-α-L-mannopyranosyl-(1→2)-6-deoxy-1-O-[(3β,16α)-3,16-dihydroxy-23,28-dioxoolean-12-en-28-yl]-β-D-galactopyranose
Synonyms Sources
quillaic acid α-L-arabinopyranosyl-(1→4)-α-L-arabinopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester ChEBI
quillaic acid glycosidic ester ChEBI
Registry Number Type Source
10518815 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
16880670 PubMed citation Europe PMC
Last Modified
20 January 2014