CHEBI:3943 - cucurbitacin D

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ChEBI Name cucurbitacin D
ChEBI ID CHEBI:3943
Definition A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 5 and 23.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H44O7
Net Charge 0
Average Mass 516.66620
Monoisotopic Mass 516.30870
InChI InChI=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
InChIKey SRPHMISUTWFFKJ-QJNWWGCFSA-N
SMILES [H][C@@]12C[C@H](O)C(=O)C(C)(C)C1=CC[C@@]1([H])[C@]3(C)C[C@@H](O)[C@]([H])([C@@](C)(O)C(=O)\C=C\C(C)(C)O)[C@@]3(C)CC(=O)[C@@]21C
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 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 Sources
(23E)-2β,16α,20,25- tetrahydroxy-9β-methyl-19-nor-10α-lanosta-5,23-diene-3,11,22-trione ChEBI
(23E)-2β,16α,20,25-tetrahydroxy-10α-cucurbita-5,23-diene-3,11,22-trione ChEBI
Elatericin A ChemIDplus
Elatericine A ChemIDplus
Manual Xrefs Databases
C00003685 KNApSAcK
C08796 KEGG COMPOUND
LMST01010106 LIPID MAPS
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Registry Numbers Types Sources
2068583 Reaxys Registry Number Reaxys
3877-86-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19185617 PubMed citation Europe PMC
20926322 PubMed citation Europe PMC
21184524 PubMed citation Europe PMC
4384331 PubMed citation Europe PMC
8858910 PubMed citation Europe PMC
Last Modified
07 February 2018