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

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This entity has been annotated by a third party. If you would like more information added to this entry, please contact ChEBI via email or GitHub.
ChEBI Name (3beta,9xi)-3-(beta-D-Glucopyranosyloxy)-14-hydroxycard-20(22)-enolide
ChEBI ID CHEBI:183683
Stars This entity has been manually annotated by a third party.
Submitter MetaboLights
Supplier Information
Download Molfile XML SDF
Formula C29H44O9
Net Charge 0
Average Mass 536.662
Monoisotopic Mass 536.29853
InChI InChI=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
InChIKey CMHWMOGWFZWDMR-GRIHHVLPSA-N
SMILES O[C@@]12[C@]3(C([C@@]4(C(CC3)C[C@@H](O[C@@H]5O[C@@H]([C@@H](O)[C@H](O)[C@H]5O)CO)CC4)C)CC[C@@]1([C@H](CC2)C=6COC(=O)C6)C)[H]
Metabolite of Species Details
Bombus terrestris (NCBI:txid30195) Found in hemolymph (BTO:0000572). See: MetaboLights Study
Bombus terrestris (NCBI:txid30195) Found in brain (BTO:0000142). See: MetaboLights Study
Bombus terrestris (NCBI:txid30195) Found in hindgut (BTO:0000510). See: MetaboLights Study
Roles Classification
Application(s): cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
(via cardiac glycoside )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (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 Xref Database
22913898 ChemSpider
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