Oleandolide

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Basic information

CAS: 68540-16-9
Standard SMILES: C[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
InChIKey: PFDLUBNRHMFBGI-HRVFELILSA-N
Molecular formula: C20H34O7
Average molar mass: 386.5 g/mol
Monoisotopic mass: 386.23045342

Overview

Oleandolide is a 14-membererd macrolide containing ten stereocentres carrying one epoxymethano, three hydroxy and five methyl substituents. It is the aglycone of the antibiotic oleandomycin. It is a spiro-epoxide, a macrolide, a triol and a cyclic ketone.

Names & identifiers

Preferred name: Oleandolide
IUPAC: (3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6,8,14-trihydroxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione

Names & synonyms

OleandolideOleandonolideOleandomycin aglycone(-)-Oleandolide68540-16-9CHEBI:29658(3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6,8,14-trihydroxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione(3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6,8,14-trihydroxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro(2.13)hexadecane-10,16-dioneRefChem:168078(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-dioneSCHEMBL3290903DTXSID50988208

Show more names

LMPK04000031Q271102116,12,14-Trihydroxy-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione

Database identifiers

CAS: 68540-16-9
PubChem CID: 443564
DTXSID: DTXSID50988208
ChEBI: CHEBI:29658

Properties

Computed structural properties

XLogP: 1.5
Topological polar surface area: 117 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 7
Rotatable bonds: 0
Heavy atoms: 27
Formal charge: 0
Complexity: 565

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Macrolides and lactone polyketides [PK04]

Related reactions

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Compound notes

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