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CHEBI:183683 - (3beta,9xi)-3-(beta-D-Glucopyranosyloxy)-14-hydroxycard-20(22)-enolide

Default Structure
ChEBI IDCHEBI:183683
ChEBI Name(3beta,9xi)-3-(beta-D-Glucopyranosyloxy)-14-hydroxycard-20(22)-enolide
Stars
SubmitterMetaboLights
DownloadsMolfile
FormulaC29H44O9
Net Charge0
Average Mass536.662
Monoisotopic Mass536.29853
SMILES[H][C@@]12CCC3C[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)CC[C@]3(C)C1CC[C@]1(C)[C@@H](C3=CC(=O)OC3)CC[C@]21O
InChIInChI=1S/C29H44O9/c1-27-8-5-17(37-26-25(34)24(33)23(32)21(13-30)38-26)12-16(27)3-4-20-19(27)6-9-28(2)18(7-10-29(20,28)35)15-11-22(31)36-14-15/h11,16-21,23-26,30,32-35H,3-10,12-14H2,1-2H3/t16?,17-,18+,19?,20+,21+,23+,24-,25+,26+,27-,28+,29-/m0/s1
InChIKeyCMHWMOGWFZWDMR-GRIHHVLPSA-N
Species of MetaboliteComponentSourceComments
Bombus terrestris (ncbitaxon:30195)
hemolymph (BTO:0000572) MetaboLights (MTBLS3637)
brain (BTO:0000142) MetaboLights (MTBLS3637)
hindgut (BTO:0000510) MetaboLights (MTBLS3637)
Roles Classification
Application:
cardioprotective agent  Any protective agent that is able to prevent damage to the heart.
ChEBI Ontology
Outgoing Relation(s)
(3beta,9xi)-3-(beta-D-Glucopyranosyloxy)-14-hydroxycard-20(22)-enolide (CHEBI:183683) is a cardenolide glycoside (CHEBI:38092)
IUPAC Name 
3-[(3S,8R,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-uran-5-one
Manual XrefsDatabases
22913898ChemSpider