CHEBI:65992 - gypsosaponin A

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ChEBI Name gypsosaponin A
ChEBI ID CHEBI:65992
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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C74H116O40
Net Charge 0
Average Mass 1645.68880
Monoisotopic Mass 1644.70429
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
SMILES [H][C@]1(OC[C@@H](O)[C@H](O)[C@H]1O)O[C@H]1[C@H](O)[C@H](O[C@@]([H])(O[C@H]2CC[C@@]3(C)[C@@]([H])(CC[C@]4(C)[C@]3([H])CC=C3[C@]5([H])CC(C)(C)CC[C@@]5([C@H](O)C[C@@]43C)C(=O)O[C@@H]3O[C@H](C)[C@H](O)[C@H](O)[C@H]3O[C@]3([H])O[C@@H](C)[C@H](O[C@]4([H])OC[C@@H](O)[C@H](O[C@]5([H])OC[C@H](O)[C@H](O)[C@H]5O[C@]5([H])OC[C@H](O)[C@H](O)[C@H]5O)[C@H]4O)[C@@H](O)[C@H]3O)[C@]2(C)C=O)[C@@H]1O[C@]1([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)C(O)=O
Metabolite of Species Details
Gypsophila oldhamiana (IPNI:154553-1) Found in root (BTO:0001188). 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.
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.
(via saponin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
11101555 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17409564 PubMed citation Europe PMC
Last Modified
20 January 2014