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 (CHEBI:66290)

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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

ChEBI ID	CHEBI:66290
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
Stars
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.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C57H90O25
Net Charge	0
Average Mass	1175.322
Monoisotopic Mass	1174.57712
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)CC[C@H](O)[C@@](C)(C=O)[C@]6([H])CC[C@@]5(C)[C@]3(C)C[C@H]4O)O[C@H](C)[C@H](O)[C@@H]2O)O[C@@H](C)[C@H](O[C@]2([H])OC[C@@H](O)[C@H](O[C@]3([H])OC[C@H](O[C@]4([H])OC[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H]2O)[C@@H](O)[C@H]1O
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

Species of Metabolite	Component	Source	Comments
Gypsophila oldhamiana (IPNI:154553-1)	root (BTO:0001188)	PubMed (16880670)

Roles Classification

Biological Roles:

plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system.

metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

Application:

immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
quillaic acid glycosidic ester	ChEBI
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

Registry Numbers	Sources
Reaxys:10518815	Reaxys

Citations