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CHEBI:65831 - elaeodendroside W

ChEBI IDCHEBI:65831
ChEBI Nameelaeodendroside W
Stars
DefinitionA cardenolide glycoside that is 3,5,11,14-tetrahydroxy-19-oxocard-20(22)-enolide glycosylated at position 3 by a β-allosyl-(1→4)-β-6-deoxyallosyl group. Isolated from Elaeodendron alluaudianum, it exhibits antiproliferative activity against human ovarian cancer and human histiocytic lymphoma cell lines.
Last Modified17 March 2016
DownloadsMolfile
FormulaC35H52O16
Net Charge0
Average Mass728.785
Monoisotopic Mass728.32554
SMILES[H][C@@]1(O[C@H]2[C@@H](O)[C@@H](O)[C@]([H])(O[C@H]3CC[C@@]4(C=O)[C@](O)(CC[C@@]5([H])[C@@]6(O)CC[C@H](C7=CC(=O)OC7)[C@@]6(C)C[C@@H](O)[C@@]54[H])C3)O[C@@H]2C)O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]1O
InChIInChI=1S/C35H52O16/c1-15-29(51-31-27(43)25(41)24(40)21(12-36)50-31)26(42)28(44)30(48-15)49-17-3-6-33(14-37)23-19(4-7-34(33,45)10-17)35(46)8-5-18(16-9-22(39)47-13-16)32(35,2)11-20(23)38/h9,14-15,17-21,23-31,36,38,40-46H,3-8,10-13H2,1-2H3/t15-,17+,18-,19-,20-,21-,23-,24-,25-,26+,27-,28-,29-,30+,31+,32-,33+,34+,35+/m1/s1
InChIKeyXPFIWTDYADXSKF-PCUDRXQQSA-N
Species of MetaboliteComponentSourceComments
Elaeodendron alluaudianum (IPNI:160641-1) stem (BTO:0001300) PubMed (19058971)
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 W (CHEBI:65831) has role antineoplastic agent (CHEBI:35610)
elaeodendroside W (CHEBI:65831) has role metabolite (CHEBI:25212)
elaeodendroside W (CHEBI:65831) is a cardenolide glycoside (CHEBI:38092)
elaeodendroside W (CHEBI:65831) is a hydroxy steroid (CHEBI:35350)
elaeodendroside W (CHEBI:65831) is a steroid aldehyde (CHEBI:131565)
elaeodendroside W (CHEBI:65831) is a steroid lactone (CHEBI:26766)
IUPAC Name 
(3β,5β,11α)-3-{[4-O-(β-D-allopyranosyl)-6-deoxy-β-D-allopyranosyl]oxy}-5,11,14-trihydroxy-19-oxocard-20(22)-enolide
Synonym  Source
sarmentosigenin-3β-O-[β-allosyl-(1→4)-β-6-deoxyalloside]ChEBI
Registry NumbersSources
Reaxys:19417814Reaxys
Citations