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CHEBI:66480 - sibiskoside

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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
anti-obesity agent  Any substance which is used to reduce or control weight.
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