CHEBI:65866 - esculeoside A

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ChEBI Name esculeoside A
ChEBI ID CHEBI:65866
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C58H95NO29
Net Charge 0
Average Mass 1270.36420
Monoisotopic Mass 1269.59898
InChI InChI=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
InChIKey VSQBWNYALURFOT-ZSFCQSFNSA-N
SMILES [H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@@]4(C)[C@@]3([H])C[C@]3([H])O[C@@]5(NC[C@@H](CO[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C[C@@H]5OC(C)=O)[C@@H](C)[C@]43[H])[C@@]1(C)CC[C@@H](C2)O[C@]1([H])O[C@H](CO)[C@H](O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O[C@]3([H])OC[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O
Metabolite of Species Details
Solanum lycopersicum (NCBI:txid4081) Found in fruit (BTO:0000486). Methanolic extract of ripe tomato fruits See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
(via alkaloid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-glucopyranoside ChEBI
Registry Number Type Source
9381913 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
12576668 PubMed citation Europe PMC
Last Modified
12 April 2013