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ChEBI
> Main
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.
Supplier Information
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Molfile
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Molfile
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
(3
R
,5
R
,6
S
,7
R
,8
R
,11
R
,12
S
,13
R
,14
S
,15
S
)-
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
View more database links
Registry Numbers
Types
Sources
3566509
Reaxys Registry Number
Reaxys
68540-16-9
CAS Registry Number
ChemIDplus
Last Modified
03 December 2019