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CHEBI:65677 - 3β-[(O-β-D-glucopyranosyl-(1→3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide

ChEBI IDCHEBI:65677
ChEBI Name3β-[(O-β-D-glucopyranosyl-(1→3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide
Stars
ASCII Name3beta-[(O-beta-D-glucopyranosyl-(1->3)-4,6-dideoxy-2-O-methyl-beta-D-gulopyranosyl)]-5beta,14beta-dihydroxy-19-oxocard-20(22)enolide
DefinitionA cardenolide glycoside that is strophanthidin attached to a 4,6-dideoxy-3-O-(β-D-glucopyranosyl)-2-O-methyl-β-D-xylo-hexopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Crossosoma bigelovii, it exhibits cytotoxic activity.
Last Modified17 March 2016
DownloadsMolfile
FormulaC36H54O14
Net Charge0
Average Mass710.814
Monoisotopic Mass710.35136
SMILES[H][C@]12CC[C@@]3(C)[C@](O)(CC[C@]3([H])C3=CC(=O)OC3)[C@]1([H])CC[C@]1(O)C[C@@H](O[C@@H]3O[C@H](C)C[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]3OC)CC[C@@]12C=O
InChIInChI=1S/C36H54O14/c1-18-12-24(49-31-29(42)28(41)27(40)25(15-37)50-31)30(45-3)32(47-18)48-20-4-9-34(17-38)22-5-8-33(2)21(19-13-26(39)46-16-19)7-11-36(33,44)23(22)6-10-35(34,43)14-20/h13,17-18,20-25,27-32,37,40-44H,4-12,14-16H2,1-3H3/t18-,20+,21-,22+,23-,24+,25-,27-,28+,29-,30-,31-,32+,33-,34+,35+,36+/m1/s1
InChIKeyVTQWFYXLYNJGCR-VYRIWNHPSA-N
Species of MetaboliteComponentSourceComments
Crossosoma bigelovii (ncbitaxon:105808)
fruit (BTO:0000486) DOI (10.1021/np8006342)
leaf (BTO:0000713) DOI (10.1021/np8006342)
flower (BTO:0000469) DOI (10.1021/np8006342)
twig (BTO:0001411) DOI (10.1021/np8006342)
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)
3β-[(O-β-D-glucopyranosyl-(1→3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide (CHEBI:65677) has functional parent strophanthidin (CHEBI:38178)
3β-[(O-β-D-glucopyranosyl-(1→3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide (CHEBI:65677) has role antineoplastic agent (CHEBI:35610)
3β-[(O-β-D-glucopyranosyl-(1→3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide (CHEBI:65677) has role metabolite (CHEBI:25212)
3β-[(O-β-D-glucopyranosyl-(1→3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide (CHEBI:65677) is a 19-oxo steroid (CHEBI:38149)
3β-[(O-β-D-glucopyranosyl-(1→3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide (CHEBI:65677) is a 5β-hydroxy steroid (CHEBI:38195)
3β-[(O-β-D-glucopyranosyl-(1→3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide (CHEBI:65677) is a cardenolide glycoside (CHEBI:38092)
3β-[(O-β-D-glucopyranosyl-(1→3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide (CHEBI:65677) is a disaccharide derivative (CHEBI:63353)
3β-[(O-β-D-glucopyranosyl-(1→3)-4,6-dideoxy-2-O-methyl-β-D-gulopyranosyl)]-5β,14β-dihydroxy-19-oxocard-20(22)enolide (CHEBI:65677) is a steroid aldehyde (CHEBI:131565)
IUPAC Name 
(3β,5β)-3-{[4,6-dideoxy-3-O-(β-D-glucopyranosyl)-2-O-methyl-β-D-xylo-hexopyranosyl]oxy}-5,14-dihydroxy-19-oxocard-20(22)-enolide
Citations