Structure Database (LMSD)

O H H O O O H O HO O H O OH
Common Name
Oleandrin
Systematic Name
(3β,5β,16β)-16-(acetyloxy)-3-[(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)oxy]-14-hydroxy-card-20(22)-enolide
Synonyms
LM ID
LMST01120025
Formula
C32H48O9
Exact Mass
Calculate m/z
576.329835
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Cardanolides and derivatives [ST0112]

String Representations

InChiKey (Click to copy)
JLPDBLFIVFSOCC-XYXFTTADSA-N
InChi (Click to copy)
InChI=1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17-,20+,21-,22-,23+,24-,25-,27-,28-,29-,30-,31+,32-/m0/s1
SMILES (Click to copy)
C1[C@@]2(C)[C@]([H])(CC[C@]3([H])[C@]2([H])CC[C@]2(C)[C@@]([H])(C4COC(=O)C=4)[C@@H](OC(=O)C)C[C@]32O)C[C@@H](O[C@H]2C[C@H](OC)[C@@H](O)[C@H](C)O2)C1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Nerium oleander (#63479)
Magnoliopsida (#3398)
Oleandrin suppresses activation of nuclear transcription factor-kappaB, activator protein-1, and c-Jun NH2-terminal kinase.,
Cancer Res, 2000
Pubmed ID: 10919658

Other Databases

CHEBI ID
59030
PubChem CID
11541511
GuidePharm ID
12618

Calculated Physicochemical Properties

Heavy Atoms 41
Rings 6
Aromatic Rings
Rotatable Bonds 6
Van der Waals Molecular Volume 559.19
Topological Polar Surface Area 124.89
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 9
logP 5.97
Molar Refractivity 151.36

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Created at
19th Jul 2021
Updated at
19th Jul 2021