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

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 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 ID CHEBI:65677
ChEBI ASCII Name 3beta-[(O-beta-D-glucopyranosyl-(1->3)-4,6-dideoxy-2-O-methyl-beta-D-gulopyranosyl)]-5beta,14beta-dihydroxy-19-oxocard-20(22)enolide
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C36H54O14
Net Charge 0
Average Mass 710.80560
Monoisotopic Mass 710.35136
InChI InChI=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
InChIKey VTQWFYXLYNJGCR-VYRIWNHPSA-N
SMILES [H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@]4(O)C[C@H](CC[C@]4(C=O)[C@@]3([H])CC[C@]12C)O[C@@H]1O[C@H](C)C[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1OC)C1=CC(=O)OC1
Metabolite of Species Details
Crossosoma bigelovii (NCBI:txid105808) Found in flower (BTO:0000469). See: DOI
Crossosoma bigelovii (NCBI:txid105808) Found in leaf (BTO:0000713). See: DOI
Crossosoma bigelovii (NCBI:txid105808) Found in fruit (BTO:0000486). See: DOI
Crossosoma bigelovii (NCBI:txid105808) Found in twig (BTO:0001411). See: DOI
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.
(via 3beta-[(O-beta-D-glucopyranosyl-(1->3)-4,6-dideoxy-2-O-methyl-beta-D-gulopyranosyl)]-5beta,14beta-dihydroxy-19-oxocard-20(22)enolide )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
(via 3beta-[(O-beta-D-glucopyranosyl-(1->3)-4,6-dideoxy-2-O-methyl-beta-D-gulopyranosyl)]-5beta,14beta-dihydroxy-19-oxocard-20(22)enolide )
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 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
Citation Waiting for Citations Type Source
19405508 PubMed citation Europe PMC
Last Modified
17 March 2016