oleandrin   Click here for help

GtoPdb Ligand ID: 12618

Synonyms: foliandrin | neriolin | PBI-05204 (mixture of botanical compounds) | PBI05204
Compound class: Natural product
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].

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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Calderón-Montaño JM, Burgos-Morón E, Guillén-Mancina E, López-Lázaro M. (2015)
Does the Nerium oleander extract PBI-05204 have potential for pancreatic cancer therapy?.
Invest New Drugs, 33 (3): 787. [PMID:25698441]
2. Francischini CRD, Mendonça CR, Barcelos KA, Silva MAM, Botelho AFM. (2022)
Antitumor effects of oleandrin in different types of cancers: Systematic review.
Toxicon, 216: 15-27. [PMID:35772506]
3. Roth MT, Cardin DB, Borazanci EH, Steinbach M, Picozzi VJ, Rosemury A, Wadlow RC, Newman RA, Berlin J. (2020)
A Phase II, Single-Arm, Open-Label, Bayesian Adaptive Efficacy and Safety Study of PBI-05204 in Patients with Stage IV Metastatic Pancreatic Adenocarcinoma.
Oncologist, 25 (10): e1446-e1450. [PMID:32452588]
4. Smith JA, Madden T, Vijjeswarapu M, Newman RA. (2001)
Inhibition of export of fibroblast growth factor-2 (FGF-2) from the prostate cancer cell lines PC3 and DU145 by Anvirzel and its cardiac glycoside component, oleandrin.
Biochem Pharmacol, 62 (4): 469-72. [PMID:11448457]
5. Van Kanegan MJ, Dunn DE, Kaltenbach LS, Shah B, He DN, McCoy DD, Yang P, Peng J, Shen L, Du L et al.. (2016)
Dual activities of the anti-cancer drug candidate PBI-05204 provide neuroprotection in brain slice models for neurodegenerative diseases and stroke.
Sci Rep, 6: 25626. [PMID:27172999]