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CHEBI:66157 - salzmannianoside A

ChEBI IDCHEBI:66157
ChEBI Namesalzmannianoside A
Stars
DefinitionA triterpenoid saponin that consists of gypsogenin attached to a α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl] residue at position 3 via a glycosidic linkage. Isolated from Serjania salzmanniana, it exhibits antifungal and molluscicidal activities.
Last Modified20 January 2014
DownloadsMolfile
FormulaC47H74O17
Net Charge0
Average Mass911.092
Monoisotopic Mass910.49260
SMILES[H][C@@]1(O[C@@H]2[C@@H](O)[C@@]([H])(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CO[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)CC[C@@]5(C)[C@]4(C)CC[C@@]3([H])[C@]2(C)C=O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
InChIInChI=1S/C47H74O17/c1-22-30(50)33(53)35(55)38(60-22)64-37-32(52)26(62-39-36(56)34(54)31(51)25(19-48)61-39)20-59-40(37)63-29-11-12-43(4)27(44(29,5)21-49)10-13-46(7)28(43)9-8-23-24-18-42(2,3)14-16-47(24,41(57)58)17-15-45(23,46)6/h8,21-22,24-40,48,50-56H,9-20H2,1-7H3,(H,57,58)/t22-,24-,25+,26-,27+,28+,29-,30-,31+,32-,33+,34-,35+,36+,37+,38-,39-,40-,43-,44-,45+,46+,47-/m0/s1
InChIKeySKHHYJVYSRMYHD-YDIXZRNLSA-N
Species of MetaboliteComponentSourceComments
Serjania salzmanniana (IPNI:785156-1) stem (BTO:0001300) PubMed (8699187)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
molluscicide  A substance used to destroy pests of the phylum Mollusca.
ChEBI Ontology
Outgoing Relation(s)
salzmannianoside A (CHEBI:66157) has functional parent gypsogenin (CHEBI:5580)
salzmannianoside A (CHEBI:66157) has role antifungal agent (CHEBI:35718)
salzmannianoside A (CHEBI:66157) has role molluscicide (CHEBI:33904)
salzmannianoside A (CHEBI:66157) has role plant metabolite (CHEBI:76924)
salzmannianoside A (CHEBI:66157) is a monocarboxylic acid (CHEBI:25384)
salzmannianoside A (CHEBI:66157) is a pentacyclic triterpenoid (CHEBI:25872)
salzmannianoside A (CHEBI:66157) is a trisaccharide derivative (CHEBI:63571)
salzmannianoside A (CHEBI:66157) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name 
(3β)-3-{[6-deoxy-α-L-mannopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl]oxy}-23-oxoolean-12-en-28-oic acid
Synonym  Source
3-O-{[β-D-glucopyranosyl-(1→4)]-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl}gypsogeninChEBI
Citations