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CHEBI:3944 - cucurbitacin E

ChEBI IDCHEBI:3944
ChEBI Namecucurbitacin E
Stars
DefinitionA cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 1, 5 and 23.
Last Modified7 February 2018
DownloadsMolfile
FormulaC32H44O8
Net Charge0
Average Mass556.696
Monoisotopic Mass556.30362
SMILES[H][C@@]12CC=C3C(C)(C)C(=O)C(O)=C[C@@]3([H])[C@]1(C)C(=O)C[C@@]1(C)[C@@]2(C)C[C@@H](O)[C@]1([H])[C@@](C)(O)C(=O)/C=C/C(C)(C)OC(C)=O
InChIInChI=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
InChIKeyNDYMQXYDSVBNLL-MUYMLXPFSA-N
Roles Classification
Biological Role:
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.
ChEBI Ontology
Outgoing Relation(s)
cucurbitacin E (CHEBI:3944) is a cucurbitacin (CHEBI:16219)
cucurbitacin E (CHEBI:3944) is a tertiary α-hydroxy ketone (CHEBI:139592)
Incoming Relation(s)
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  Source
Cucurbitacin EKEGG COMPOUND
2,16α,20,25-tetrahydroxy-9-methyl-19-nor-9β,10α-lanosta-1,5,23-triene-3,11,22-trione 25-acetateChEBI
(23E)-25-acetyloxy-2,16α,20-trihydroxy-9β-methyl-19-nor-10α-lanosta-1,5,23-triene-3,11,22-trioneChemIDplus
α-ElaterinChemIDplus
α-ElaterineChemIDplus
Manual XrefsDatabases
C08797KEGG COMPOUND
LMST01010107LIPID MAPS
C00003686KNApSAcK
Registry NumbersSources
Reaxys:2343323Reaxys
CAS:18444-66-1KEGG COMPOUND
CAS:18444-66-1ChemIDplus
Citations