CHEBI:65829 - elaeodendroside U

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ChEBI Name elaeodendroside U
ChEBI ID CHEBI:65829
Definition A cardenolide glycoside that is carda-4,20(22)-dienolide substituted by hydroxy groups at positions 2 and 14, an oxo group at position 12 and a (4-deoxy-3-O-methyl-α-L-erythro-pentopyranosyl)oxy moiety at position 3 (the 2α,3β stereoisomer). Isolated from from wood of Elaeodendron tangenala, it exhibits antiproliferative activity against A2780 human ovarian cancer cells.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C29H40O9
Net Charge 0
Average Mass 532.62250
Monoisotopic Mass 532.26723
InChI InChI=1S/C29H40O9/c1-27-13-20(30)22(38-26-25(33)21(35-3)7-9-36-26)11-16(27)4-5-18-19(27)12-23(31)28(2)17(6-8-29(18,28)34)15-10-24(32)37-14-15/h10-11,17-22,25-26,30,33-34H,4-9,12-14H2,1-3H3/t17-,18-,19+,20-,21+,22-,25+,26+,27+,28+,29+/m1/s1
InChIKey PESZVAPIHIOBQI-HDOPOQRKSA-N
SMILES [H][C@]1(OCC[C@H](OC)[C@@H]1O)O[C@@H]1C=C2CC[C@]3([H])[C@]([H])(CC(=O)[C@]4(C)[C@H](CC[C@]34O)C3=CC(=O)OC3)[C@@]2(C)C[C@H]1O
Metabolite of Species Details
Elaeodendron tangenala (NCBI:txid123414) Found in xylem (BTO:0001468). Previous component: wood; See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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 elaeodendroside U (CHEBI:65829) has role antineoplastic agent (CHEBI:35610)
elaeodendroside U (CHEBI:65829) has role metabolite (CHEBI:25212)
elaeodendroside U (CHEBI:65829) is a cardenolide glycoside (CHEBI:38092)
elaeodendroside U (CHEBI:65829) is a monosaccharide derivative (CHEBI:63367)
IUPAC Name
(2α,3β)-3-[(4-deoxy-3-O-methyl-α-L-erythro-pentopyranosyl)oxy]-2,14-dihydroxy-12-oxocarda-4,20(22)-dienolide
Synonym Source
4-[(2R,3R,8R,9S,10R,13R,14S,17R)-2,14-dihydroxy-3-{[(2S,3S,4S)-3-hydroxy-4-methoxytetrahydro-2H-pyran-2-yl]oxy}-10,13-dimethyl-12-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]furan-2(5H)-one ChEBI
Manual Xref Database
20567916 ChemSpider
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Registry Number Type Source
11195448 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17547460 PubMed citation Europe PMC
Last Modified
17 January 2013