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CHEBI:65973 - glochierioside A

ChEBI IDCHEBI:65973
ChEBI Nameglochierioside A
Stars
DefinitionA triterpenoid saponin that is 3β,16β,28-trihydroxyolean-12-ene substituted by a β-benzoyloxy group at position 22 and a 3-O-(β-D-glucopyranosyl)-α-L-arabinopyranosyl group at position 3 via a glycosidic linkage. Isolated from Glochidion eriocarpum, it exhibits cytotoxicity against human cancer cell lines.
Last Modified20 January 2014
DownloadsMolfile
FormulaC48H72O14
Net Charge0
Average Mass873.090
Monoisotopic Mass872.49221
SMILES[H][C@@]1(O[C@@H]2[C@@H](O)[C@]([H])(O[C@H]3CC[C@]4(C)[C@@]5([H])CC=C6[C@]7([H])CC(C)(C)C[C@@H](OC(=O)c8ccccc8)[C@]7(CO)[C@@H](O)C[C@@]6(C)[C@]5(C)CC[C@@]4([H])C3(C)C)OC[C@@H]2O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C48H72O14/c1-43(2)19-27-26-13-14-31-45(5)17-16-33(61-41-38(56)39(28(51)23-58-41)62-42-37(55)36(54)35(53)29(22-49)59-42)44(3,4)30(45)15-18-46(31,6)47(26,7)20-32(52)48(27,24-50)34(21-43)60-40(57)25-11-9-8-10-12-25/h8-13,27-39,41-42,49-56H,14-24H2,1-7H3/t27-,28-,29+,30-,31+,32-,33-,34+,35+,36-,37+,38+,39-,41-,42-,45-,46+,47+,48-/m0/s1
InChIKeyGRNFGBBADZIGAQ-IJBRHCHSSA-N
Species of MetaboliteComponentSourceComments
Glochidion eriocarpum (IPNI:349360-1) aerial part (BTO:0001658) PubMed (19122328)
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
glochierioside A (CHEBI:65973) has parent hydride oleanane (CHEBI:36481)
glochierioside A (CHEBI:65973) has role antineoplastic agent (CHEBI:35610)
glochierioside A (CHEBI:65973) has role plant metabolite (CHEBI:76924)
glochierioside A (CHEBI:65973) is a benzoate ester (CHEBI:36054)
glochierioside A (CHEBI:65973) is a diol (CHEBI:23824)
glochierioside A (CHEBI:65973) is a disaccharide derivative (CHEBI:63353)
glochierioside A (CHEBI:65973) is a pentacyclic triterpenoid (CHEBI:25872)
glochierioside A (CHEBI:65973) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name 
(3β,16β,22β)-3-{[3-O-(β-D-glucopyranosyl)-α-L-arabinopyranosyl]oxy}-16,28-dihydroxyolean-12-en-22-yl benzoate
Synonym  Source
22β-benzoyloxy-3β,16β,28-trihydroxyolean-12-ene 3-O-[β-D-glucopyranosyl-(1→3)-α-L-arabinopyranoside]ChEBI
Registry NumbersSources
Reaxys:19204940Reaxys
Citations