CHEBI:3941 - cucurbitacin B

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ChEBI Name cucurbitacin B
ChEBI ID CHEBI:3941
Definition A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 5 and 23; a hydroxy function at C-25 is acetylated.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C32H46O8
Net Charge 0
Average Mass 558.70280
Monoisotopic Mass 558.31927
InChI InChI=1S/C32H46O8/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/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1
InChIKey IXQKXEUSCPEQRD-DKRGWESNSA-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)OC(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 B (CHEBI:3941) has parent hydride lanostane (CHEBI:20265)
cucurbitacin B (CHEBI:3941) is a cucurbitacin (CHEBI:16219)
cucurbitacin B (CHEBI:3941) is a secondary α-hydroxy ketone (CHEBI:2468)
cucurbitacin B (CHEBI:3941) is a tertiary α-hydroxy ketone (CHEBI:139592)
Incoming 23,24-dihydrocucurbitacin B (CHEBI:62217) has functional parent cucurbitacin B (CHEBI:3941)
IUPAC Name
(2S,4R,23E)-2,16β,20-trihydroxy-9β,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-5,23-dien-25-yl acetate
Synonyms Sources
1,2-dihydro-α-elaterin ChemIDplus
2β,16α,20,25-tetrahydroxy-9-methyl-19-nor-9β,10α-lanosta-5,23-diene-3,11,22-trione, 25-acetate ChemIDplus
2β,16α,20,25-tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9β,10α-lanosta-5,23-dien-25-yl acetate ChEBI
cucurbitacin B UniProt
Manual Xrefs Databases
C00003683 KNApSAcK
C08794 KEGG COMPOUND
LMST01010104 LIPID MAPS
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Registry Numbers Types Sources
2068869 Reaxys Registry Number Reaxys
6199-67-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
18309509 PubMed citation Europe PMC
18442812 PubMed citation Europe PMC
18561312 PubMed citation Europe PMC
19700240 PubMed citation Europe PMC
20153103 PubMed citation Europe PMC
20483353 PubMed citation Europe PMC
21344491 PubMed citation Europe PMC
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5640163 PubMed citation Europe PMC
Last Modified
07 February 2018