gypsosaponin B (CHEBI:65993)

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CHEBI:65993 - gypsosaponin B

ChEBI ID	CHEBI:65993
ChEBI Name	gypsosaponin B
Stars
Definition	A triterpenoid saponin with gypsogenin as the aglycone species. It is isolated from the roots of Gypsophila oldhamiana and exhibits inhibitory activity against pancreatic lipase.
Last Modified	16 March 2015
Downloads	Molfile

Formula	C71H112O36
Net Charge	0
Average Mass	1541.641
Monoisotopic Mass	1540.69333
SMILES	[H][C@@]1(O[C@@H]2[C@@H](O[C@]3([H])OC[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@@H](C(=O)OC)O[C@@]2([H])O[C@H]2CC[C@]3(C)[C@@]4([H])CC=C5[C@]6([H])CC(C)(C)CC[C@]6(C(=O)O[C@@H]6O[C@H](C)[C@H](O)[C@H](O)[C@H]6O[C@]6([H])O[C@@H](C)[C@H](O[C@]7([H])OC[C@@H](O)[C@H](O)[C@H]7O)[C@@H](O[C@]7([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)CC[C@@]5(C)[C@]4(C)CC[C@@]3([H])[C@]2(C)C=O)O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O
InChI	InChI=1S/C71H112O36/c1-26-37(77)44(84)55(105-62-50(90)53(103-60-47(87)42(82)40(80)32(21-72)98-60)51(27(2)97-62)101-58-45(85)38(78)30(75)23-94-58)63(96-26)107-65(92)71-18-16-66(3,4)20-29(71)28-10-11-35-67(5)14-13-36(68(6,25-74)34(67)12-15-70(35,8)69(28,7)17-19-71)100-64-56(106-61-48(88)43(83)41(81)33(22-73)99-61)52(49(89)54(104-64)57(91)93-9)102-59-46(86)39(79)31(76)24-95-59/h10,25-27,29-56,58-64,72-73,75-90H,11-24H2,1-9H3/t26-,27+,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-,58+,59+,60+,61+,62+,63+,64-,67+,68+,69-,70-,71+/m1/s1
InChIKey	AGJYKHGGYNIQGQ-KSEKXDIWSA-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 B (CHEBI:65993) has functional parent gypsogenin (CHEBI:5580)
	gypsosaponin B (CHEBI:65993) has parent hydride oleanane (CHEBI:36481)
	gypsosaponin B (CHEBI:65993) has role EC 3.1.1.3 (triacylglycerol lipase) inhibitor (CHEBI:65001)
	gypsosaponin B (CHEBI:65993) has role plant metabolite (CHEBI:76924)
	gypsosaponin B (CHEBI:65993) is a aldehyde (CHEBI:17478)
	gypsosaponin B (CHEBI:65993) is a methyl ester (CHEBI:25248)
	gypsosaponin B (CHEBI:65993) is a pentacyclic triterpenoid (CHEBI:25872)
	gypsosaponin B (CHEBI:65993) is a triterpenoid saponin (CHEBI:61778)

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

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

Registry Numbers	Sources
Reaxys:11101556	Reaxys

Citations