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CHEBI:65829 - elaeodendroside U

ChEBI IDCHEBI:65829
ChEBI Nameelaeodendroside U
Stars
DefinitionA 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.
Last Modified17 January 2013
DownloadsMolfile
FormulaC29H40O9
Net Charge0
Average Mass532.630
Monoisotopic Mass532.26723
SMILES[H][C@@]1(O[C@@H]2C=C3CC[C@]4([H])[C@]([H])(CC(=O)[C@]5(C)[C@@H](C6=CC(=O)OC6)CC[C@]45O)[C@@]3(C)C[C@H]2O)OCC[C@H](OC)[C@@H]1O
InChIInChI=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
InChIKeyPESZVAPIHIOBQI-HDOPOQRKSA-N
Species of MetaboliteComponentSourceComments
Elaeodendron tangenala (ncbitaxon:123414) xylem (BTO:0001468) PubMed (17547460) Previous component: wood;
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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)-oneChEBI
Manual XrefsDatabases
20567916ChemSpider
Registry NumbersSources
Reaxys:11195448Reaxys
Citations