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CHEBI:3943 - cucurbitacin D

ChEBI IDCHEBI:3943
ChEBI Namecucurbitacin D
Stars
DefinitionA cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 5 and 23.
Last Modified7 February 2018
DownloadsMolfile
FormulaC30H44O7
Net Charge0
Average Mass516.675
Monoisotopic Mass516.30870
SMILES[H][C@@]12CC=C3C(C)(C)C(=O)[C@@H](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)O
InChIInChI=1S/C30H44O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-12,17-20,23,31-32,36-37H,10,13-15H2,1-8H3/b12-11+/t17-,18+,19-,20+,23+,27+,28-,29+,30+/m1/s1
InChIKeySRPHMISUTWFFKJ-QJNWWGCFSA-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 D (CHEBI:3943) has parent hydride lanostane (CHEBI:20265)
cucurbitacin D (CHEBI:3943) is a cucurbitacin (CHEBI:16219)
cucurbitacin D (CHEBI:3943) is a secondary α-hydroxy ketone (CHEBI:2468)
cucurbitacin D (CHEBI:3943) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name 
(2S,4R,23E)-2,16,20,25-tetrahydroxy-9β,10,14-trimethyl-4,9-cyclo-9,10-seco-16α-cholesta-5,23-diene-1,11,22-trione
Synonyms  Source
(23E)-2β,16α,20,25- tetrahydroxy-9β-methyl-19-nor-10α-lanosta-5,23-diene-3,11,22-trioneChEBI
Elatericin AChemIDplus
Elatericine AChemIDplus
(23E)-2β,16α,20,25-tetrahydroxy-10α-cucurbita-5,23-diene-3,11,22-trioneChEBI
Manual XrefsDatabases
C08796KEGG COMPOUND
LMST01010106LIPID MAPS
C00003685KNApSAcK
Registry NumbersSources
Reaxys:2068583Reaxys
CAS:3877-86-9KEGG COMPOUND
CAS:3877-86-9ChemIDplus
Citations