gypsosaponin A (CHEBI:65992)

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CHEBI:65992 - gypsosaponin A

ChEBI ID	CHEBI:65992
ChEBI Name	gypsosaponin A
Stars
Definition	A triterpenoid saponin with quillaic acid as the aglycone species. It is isolated from the roots of Gypsophila oldhamiana and exhibits inhibitory activity against pancreatic lipase.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C74H116O40
Net Charge	0
Average Mass	1645.702
Monoisotopic Mass	1644.70429
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@]7([H])O[C@H](C(=O)O)[C@@H](O)[C@H](O[C@]8([H])OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@]7([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)[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@H](O)[C@H]3O[C@]3([H])OC[C@H](O)[C@H](O)[C@H]3O)[C@H]2O)[C@@H](O)[C@H]1O
InChI	InChI=1S/C74H116O40/c1-25-38(82)44(88)57(112-63-49(93)45(89)52(26(2)104-63)107-62-51(95)53(32(80)23-101-62)108-65-56(41(85)31(79)22-102-65)111-61-47(91)40(84)30(78)21-100-61)66(103-25)114-68(98)74-16-15-69(3,4)17-28(74)27-9-10-35-70(5)13-12-37(71(6,24-76)34(70)11-14-72(35,7)73(27,8)18-36(74)81)106-67-58(113-64-48(92)43(87)42(86)33(19-75)105-64)54(50(94)55(110-67)59(96)97)109-60-46(90)39(83)29(77)20-99-60/h9,24-26,28-58,60-67,75,77-95H,10-23H2,1-8H3,(H,96,97)/t25-,26+,28+,29-,30+,31+,32-,33-,34-,35-,36-,37+,38+,39+,40+,41+,42+,43+,44+,45+,46-,47-,48-,49-,50+,51-,52+,53+,54+,55+,56-,57-,58-,60+,61+,62+,63+,64+,65+,66+,67-,70+,71+,72-,73-,74-/m1/s1
InChIKey	ZIERMPRIKLCOAH-UFFRUREHSA-N

Species of Metabolite	Component	Source	Comments
Gypsophila oldhamiana (IPNI:154553-1)	root (BTO:0001188)	PubMed (17409564)

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.

EC 3.1.1.3 (triacylglycerol lipase) inhibitor Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of triacylglycerol lipase (EC 3.1.1.3).

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

ChEBI Ontology

Outgoing Relation(s)
	gypsosaponin A (CHEBI:65992) has functional parent quillaic acid (CHEBI:8710)
	gypsosaponin A (CHEBI:65992) has parent hydride oleanane (CHEBI:36481)
	gypsosaponin A (CHEBI:65992) has role EC 3.1.1.3 (triacylglycerol lipase) inhibitor (CHEBI:65001)
	gypsosaponin A (CHEBI:65992) has role plant metabolite (CHEBI:76924)
	gypsosaponin A (CHEBI:65992) is a aldehyde (CHEBI:17478)
	gypsosaponin A (CHEBI:65992) is a carboxylic ester (CHEBI:33308)
	gypsosaponin A (CHEBI:65992) is a pentacyclic triterpenoid (CHEBI:25872)
	gypsosaponin A (CHEBI:65992) is a triterpenoid saponin (CHEBI:61778)

IUPAC Name
α-L-arabinopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-6-deoxy-α-L-mannopyranosyl-(1→2)-6-deoxy-1-O-[(3β,16α)-3-{[β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranuronosyl]oxy}-16-hydroxy-23,28-dioxoolean-12-en-28-yl]-β-D-galactopyranose

Synonym	Source
3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-α-L-arabinopyranosyl-(1→2)α-L-arabinopyranosyl-(1→3)β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside	ChEBI

Registry Numbers	Sources
Reaxys:11101555	Reaxys

Citations