CHEBI:29658 - oleandolide

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ChEBI Name oleandolide
ChEBI ID CHEBI:29658
Definition A 14-membererd macrolide containing ten stereocentres carrying one epoxymethano, three hydroxy and five methyl substituents. It is the aglycone of the antibiotic oleandomycin.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H34O7
Net Charge 0
Average Mass 386.47980
Monoisotopic Mass 386.23045
InChI InChI=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
InChIKey PFDLUBNRHMFBGI-HRVFELILSA-N
SMILES C[C@H]1C[C@@]2(CO2)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@H]1O
ChEBI Ontology
Outgoing 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 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 Sources
(−)-oleandolide ChemIDplus
Oleandolide KEGG COMPOUND
Oleandomycin aglycone ChemIDplus
Oleandonolide ChemIDplus
Manual Xref Database
LMPK04000031 LIPID MAPS
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Registry Numbers Types Sources
3566509 Reaxys Registry Number Reaxys
68540-16-9 CAS Registry Number ChemIDplus
Last Modified
03 December 2019