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CHEBI:65690 - cumingianoside B

ChEBI IDCHEBI:65690
ChEBI Namecumingianoside B
Stars
DefinitionA triterpenoid saponin that is 13,30-cyclodammarane-3,7,23,24,25-pentol esterified to the corresponding acetate at position 3 and attached to a β-D-glucopyranosyl residue at position 7 via a glycosidic linkage. Isolated from Dysoxylum cumingianum, it exhibits antileukemic activity.
Last Modified20 January 2014
DownloadsMolfile
FormulaC38H64O11
Net Charge0
Average Mass696.919
Monoisotopic Mass696.44486
SMILES[H][C@]12CC[C@]34C[C@]3(CC[C@@]4([H])[C@@H](C)C[C@@H](O)[C@H](O)C(C)(C)O)[C@]1(C)[C@]([H])(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C[C@@]1([H])C(C)(C)[C@H](OC(C)=O)CC[C@]21C
InChIInChI=1S/C38H64O11/c1-19(15-22(41)31(45)34(5,6)46)21-9-14-38-18-37(21,38)13-10-24-35(7)12-11-26(47-20(2)40)33(3,4)25(35)16-27(36(24,38)8)49-32-30(44)29(43)28(42)23(17-39)48-32/h19,21-32,39,41-46H,9-18H2,1-8H3/t19-,21-,22+,23+,24+,25-,26+,27+,28+,29-,30+,31-,32-,35+,36-,37+,38+/m0/s1
InChIKeyLEUVBPJNWLQXPO-GRYJPLGOSA-N
Species of MetaboliteComponentSourceComments
Dysoxylum cumingianum (IPNI:578103-1) leaf (BTO:0000713) DOI (10.1021/jo00051a050)
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)
cumingianoside B (CHEBI:65690) has role antineoplastic agent (CHEBI:35610)
cumingianoside B (CHEBI:65690) has role plant metabolite (CHEBI:76924)
cumingianoside B (CHEBI:65690) is a acetate ester (CHEBI:47622)
cumingianoside B (CHEBI:65690) is a monosaccharide derivative (CHEBI:63367)
cumingianoside B (CHEBI:65690) is a pentacyclic triterpenoid (CHEBI:25872)
cumingianoside B (CHEBI:65690) is a secondary alcohol (CHEBI:35681)
cumingianoside B (CHEBI:65690) is a triterpenoid saponin (CHEBI:61778)
cumingianoside B (CHEBI:65690) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(3α,7α,17α,20S,23R,24S)-7-(β-D-glucopyranosyloxy)-23,24,25-trihydroxy-13,30-cyclodammaran-3-yl acetate
Synonym  Source
3-O-acetyl-3α,7α,23,24,25-pentahydroxy-14,18-cycloapoeuphanyl 7-O-β-D-glucopyranosideChEBI
Registry NumbersSources
Reaxys:5842923Reaxys
Citations