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CHEBI:66480 - sibiskoside

Default Structure
ChEBI IDCHEBI:66480
ChEBI Namesibiskoside
Stars
DefinitionA monoterpene glycoside that is geraniol-5,10-olide glycosylated at position 1 by a β-D-glucopyranosyl group. Isolated from the aerial parts of Sibiraea angustata, it exhibits anti-obesity activity.
Last Modified3 July 2013
DownloadsMolfile
FormulaC16H24O8
Net Charge0
Average Mass344.360
Monoisotopic Mass344.14712
SMILESCC(C)=C[C@H]1C/C(=C/CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)O1
InChIInChI=1S/C16H24O8/c1-8(2)5-10-6-9(15(21)23-10)3-4-22-16-14(20)13(19)12(18)11(7-17)24-16/h3,5,10-14,16-20H,4,6-7H2,1-2H3/b9-3-/t10-,11+,12+,13-,14+,16+/m0/s1
InChIKeyAYOGZIXAHOAPOK-QKAQTOFFSA-N
Species of MetaboliteComponentSourceComments
Sibiraea angustata (ncbitaxon:1055022) aerial part (BTO:0001658) PubMed (19252323)
Roles Classification
Biological Roles:
anti-obesity agent  Any substance which is used to reduce or control weight.
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)
sibiskoside (CHEBI:66480) has role anti-obesity agent (CHEBI:74518)
sibiskoside (CHEBI:66480) has role metabolite (CHEBI:25212)
sibiskoside (CHEBI:66480) is a monosaccharide derivative (CHEBI:63367)
sibiskoside (CHEBI:66480) is a monoterpene glycoside (CHEBI:72293)
sibiskoside (CHEBI:66480) is a terpene lactone (CHEBI:37668)
sibiskoside (CHEBI:66480) is a β-D-glucoside (CHEBI:22798)
sibiskoside (CHEBI:66480) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(2Z)-2-[(5R)-5-(2-methylprop-1-en-1-yl)-2-oxodihydrofuran-3(2H)-ylidene]ethyl β-D-glucopyranoside
Synonym  Source
1-O-β-D-glucopyranosyl-geraniol-5,10-olideChEBI
Registry NumbersSources
Reaxys:19888886Reaxys
Citations