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 No supplier information found for this compound.
Download Molfile XML SDF
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
Last Modified
12 April 2013