oleandrin   Click here for help

GtoPdb Ligand ID: 12618

Synonyms: foliandrin | neriolin | PBI-05204 (mixture of botanical compounds) | PBI05204
Compound class: Natural product or derivative
Comment: Oleandrin is a plant-derived glycoside. It has been associated with a range of biological effects in animals [5], including potential anti-tumour activity [1-3]. Inhibition of FGF-2 export from prostate cancer cells has been reported, and this is proposed as a potential mechanism underlying its anti-tumour effect [4].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 120.75
Molecular weight 576.72
XLogP 3.68
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]5(C)[C@@H](C6=CC(=O)OC6)[C@H](C[C@]45O)OC(=O)C)C2)OC)O
Isomeric SMILES C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(C[C@@H]([C@@H]5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)O
InChI 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
InChI Key JLPDBLFIVFSOCC-XYXFTTADSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
Synonyms Click here for help
foliandrin | neriolin | PBI-05204 (mixture of botanical compounds) | PBI05204
Database Links Click here for help
BindingDB Ligand 50465465
ChEMBL Ligand CHEMBL4285883
DrugBank Ligand DB12843
GtoPdb PubChem SID 479821408
PubChem CID 11541511
Search Google for chemical match using the InChIKey JLPDBLFIVFSOCC-XYXFTTADSA-N
Search Google for chemicals with the same backbone JLPDBLFIVFSOCC
UniChem Compound Search for chemical match using the InChIKey JLPDBLFIVFSOCC-XYXFTTADSA-N
UniChem Connectivity Search for chemical match using the InChIKey JLPDBLFIVFSOCC-XYXFTTADSA-N