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CHEBI:29658 - oleandolide

ChEBI IDCHEBI:29658
ChEBI Nameoleandolide
Stars
DefinitionA 14-membererd macrolide containing ten stereocentres carrying one epoxymethano, three hydroxy and five methyl substituents. It is the aglycone of the antibiotic oleandomycin.
Last Modified3 December 2019
DownloadsMolfile
FormulaC20H34O7
Net Charge0
Average Mass386.485
Monoisotopic Mass386.23045
SMILESC[C@@H]1[C@@H](O)[C@@H](C)C[C@@]2(CO2)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@H](C)[C@H]1O
InChIInChI=1S/C20H34O7/c1-9-7-20(8-26-20)18(24)12(4)16(22)10(2)14(6)27-19(25)13(5)17(23)11(3)15(9)21/h9-17,21-23H,7-8H2,1-6H3/t9-,10-,11+,12+,13+,14+,15-,16-,17-,20+/m0/s1
InChIKeyPFDLUBNRHMFBGI-HRVFELILSA-N
ChEBI Ontology
Outgoing Relation(s)
oleandolide (CHEBI:29658) is a cyclic ketone (CHEBI:3992)
oleandolide (CHEBI:29658) is a macrolide (CHEBI:25106)
oleandolide (CHEBI:29658) is a spiro-epoxide (CHEBI:133131)
oleandolide (CHEBI:29658) is a triol (CHEBI:27136)
Incoming Relation(s)
3-O-(α-L-oleandrosyl)oleandolide (CHEBI:29613) has functional parent oleandolide (CHEBI:29658)
3-O-(α-L-olivosyl)oleandolide (CHEBI:29614) has functional parent oleandolide (CHEBI:29658)
oleandomycin (CHEBI:16869) has functional parent oleandolide (CHEBI:29658)
IUPAC Name 
(3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-6,12,14-trihydroxy-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione
Synonyms  Source
OleandolideKEGG COMPOUND
Oleandomycin aglyconeChemIDplus
OleandonolideChemIDplus
(−)-oleandolideChemIDplus
Manual XrefsDatabases
LMPK04000031LIPID MAPS
Registry NumbersSources
Reaxys:3566509Reaxys
CAS:68540-16-9KEGG COMPOUND
CAS:68540-16-9ChemIDplus