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CHEBI:4321 - daphnetoxin

ChEBI IDCHEBI:4321
ChEBI Namedaphnetoxin
Stars
DefinitionA daphnane-type orthoester diterpene with potential cholesterol-lowering activity, found exclusively in plants of the family Thymelaeaceae.
Last Modified7 February 2018
DownloadsMolfile
FormulaC27H30O8
Net Charge0
Average Mass482.529
Monoisotopic Mass482.19407
SMILES[H][C@@]12[C@@H]3O[C@]3(CO)[C@@H](O)[C@]3(O)C(=O)C(C)=C[C@@]3([H])[C@]13O[C@]1(c4ccccc4)O[C@H]2[C@](C(=C)C)(C[C@H]3C)O1
InChIInChI=1S/C27H30O8/c1-13(2)23-11-15(4)26-17-10-14(3)19(29)25(17,31)22(30)24(12-28)21(32-24)18(26)20(23)33-27(34-23,35-26)16-8-6-5-7-9-16/h5-10,15,17-18,20-22,28,30-31H,1,11-12H2,2-4H3/t15-,17-,18-,20-,21+,22-,23-,24+,25-,26+,27-/m1/s1
InChIKeyLGEROVMQYFTBDI-FFIGBMOQSA-N
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
daphnetoxin (CHEBI:4321) has functional parent daphnane (CHEBI:36058)
daphnetoxin (CHEBI:4321) is a diterpene alkaloid (CHEBI:23847)
daphnetoxin (CHEBI:4321) is a epoxide (CHEBI:32955)
daphnetoxin (CHEBI:4321) is a ortho ester (CHEBI:71989)
daphnetoxin (CHEBI:4321) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name 
(2S,3aR,3bS,3cS,4aR,5S,5aS,8aR,8bR,9R,10aR)-5,5a-dihydroxy-4a-(hydroxymethyl)-10a-isopropenyl-7,9-dimethyl-2-phenyl-3a,3b,3c,4a,5,5a,8a,9,10,10a-decahydro-6H-2,8b-epoxyoxireno[6,7]azuleno[5,4-e][1,3]benzodioxol-6-one
Synonym  Source
(2S)-3aβ,3bβ,3cβ,4a,5,5a,8aα,9,10,10a-decahydro-5β,5aβ-dihydroxy-4aβ-hydroxymethyl-7,9α-dimethyl-10aβ-(1-methylethenyl)-2-phenyl-6H-2,8bα-epoxyoxireno[6,7]azuleno[5,4-e]-1,3-benzodioxol-6-oneChEBI
Manual XrefsDatabases
C09080KEGG COMPOUND
C00003420KNApSAcK
Registry NumbersSources
Beilstein:4281932Beilstein
CAS:28164-88-7KEGG COMPOUND
CAS:28164-88-7ChemIDplus
Citations