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CHEBI:65866 - esculeoside A

ChEBI IDCHEBI:65866
ChEBI Nameesculeoside A
Stars
DefinitionA steroid saponin that is spirosolane-3,23,27-triol in which the hydroxy group at position 23 is acetylated and the hydroxy groups at positions 3 and 27 are glycosylated by lycotetraosyl and a β-D-glucopyranosyl moieties respectively. Isolated from the fruits of Lycopersicon esculentum, it exhibits cytotoxic activity.
Last Modified12 April 2013
DownloadsMolfile
FormulaC58H95NO29
Net Charge0
Average Mass1270.376
Monoisotopic Mass1269.59898
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](CO)O[C@@]2([H])O[C@@H]2[C@H](O)[C@@H](O)[C@]([H])(O[C@H]3CC[C@@]4(C)[C@@]([H])(CC[C@]5([H])[C@]4([H])CC[C@@]4(C)[C@@]5([H])C[C@]5([H])O[C@@]6(NC[C@@H](CO[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)C[C@@H]6OC(C)=O)[C@@H](C)[C@]45[H])C3)O[C@@H]2CO)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C58H95NO29/c1-21-36-30(88-58(21)35(79-22(2)64)11-23(14-59-58)19-77-51-45(74)41(70)38(67)31(15-60)81-51)13-28-26-6-5-24-12-25(7-9-56(24,3)27(26)8-10-57(28,36)4)80-53-47(76)43(72)48(34(18-63)84-53)85-55-50(87-54-46(75)42(71)39(68)32(16-61)82-54)49(40(69)33(17-62)83-55)86-52-44(73)37(66)29(65)20-78-52/h21,23-55,59-63,65-76H,5-20H2,1-4H3/t21-,23-,24-,25-,26+,27-,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-/m0/s1
InChIKeyVSQBWNYALURFOT-ZSFCQSFNSA-N
Species of MetaboliteComponentSourceComments
Solanum lycopersicum (ncbitaxon:4081) fruit (BTO:0000486) PubMed (12576668) Methanolic extract of ripe tomato fruits
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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)
esculeoside A (CHEBI:65866) has role antineoplastic agent (CHEBI:35610)
esculeoside A (CHEBI:65866) has role metabolite (CHEBI:25212)
esculeoside A (CHEBI:65866) is a azaspiro compound (CHEBI:35624)
esculeoside A (CHEBI:65866) is a oxaspiro compound (CHEBI:37948)
esculeoside A (CHEBI:65866) is a saponin (CHEBI:26605)
esculeoside A (CHEBI:65866) is a steroid alkaloid (CHEBI:26767)
esculeoside A (CHEBI:65866) is a steroid saponin (CHEBI:61655)
IUPAC Name 
(3β,5α,22α,23S,25S)-27-(β-D-glucopyranosyloxy)-3-{[β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl]oxy}spirosolan-23-yl acetate
Synonym  Source
(23S,25S)-23-acetoxy-5α,22αN-3β,27-dihydroxyspirosolan-3-O-β-lycotetraosyl-27-O-β-D-glucopyranosideChEBI
Registry NumbersSources
Reaxys:9381913Reaxys
Citations