oleandrin   Click here for help

GtoPdb Ligand ID: 12618

Synonyms: foliandrin | neriolin | PBI-05204 (mixture of botanical compounds) | PBI05204
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
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
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