CHEBI:3944 - cucurbitacin E

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ChEBI Name cucurbitacin E
ChEBI ID CHEBI:3944
Definition A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 1, 5 and 23.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C32H44O8
Net Charge 0
Average Mass 556.68700
Monoisotopic Mass 556.30362
InChI InChI=1S/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1
InChIKey NDYMQXYDSVBNLL-MUYMLXPFSA-N
SMILES [H][C@@]12CC=C3[C@@]([H])(C=C(O)C(=O)C3(C)C)[C@]1(C)C(=O)C[C@]1(C)[C@]([H])([C@H](O)C[C@@]21C)[C@@](C)(O)C(=O)\C=C\C(C)(C)OC(C)=O
Roles Classification
Biological Role(s): allelochemical
A class of secondary metabolites developed by many plants to influence the behaviour, growth or survival of herbivores, and thus acting as a defence against herbivory.
(via cucurbitacin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cucurbitacin E (CHEBI:3944) is a cucurbitacin (CHEBI:16219)
cucurbitacin E (CHEBI:3944) is a tertiary α-hydroxy ketone (CHEBI:139592)
Incoming cucurbitacin E 2-O-β-D-glucopyranoside (CHEBI:68916) has functional parent cucurbitacin E (CHEBI:3944)
IUPAC Name
(4R,23E)-2,16α,20-trihydroxy-9β,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-yl acetate
Synonyms Sources
(23E)-25-acetyloxy-2,16α,20-trihydroxy-9β-methyl-19-nor-10α-lanosta-1,5,23-triene-3,11,22-trione ChemIDplus
2,16α,20,25-tetrahydroxy-9-methyl-19-nor-9β,10α-lanosta-1,5,23-triene-3,11,22-trione 25-acetate ChEBI
α-Elaterin ChemIDplus
α-Elaterine ChemIDplus
Cucurbitacin E KEGG COMPOUND
Manual Xrefs Databases
C00003686 KNApSAcK
C08797 KEGG COMPOUND
LMST01010107 LIPID MAPS
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Registry Numbers Types Sources
18444-66-1 CAS Registry Number ChemIDplus
2343323 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
13611647 PubMed citation Europe PMC
15908139 PubMed citation Europe PMC
19177898 PubMed citation Europe PMC
19816711 PubMed citation Europe PMC
20110807 PubMed citation Europe PMC
20347305 PubMed citation Europe PMC
4384331 PubMed citation Europe PMC
Last Modified
07 February 2018