oleuropein   Click here for help

GtoPdb Ligand ID: 11027

Comment: Oleuropein is one of the main phenolic compounds found in the European olive tree Olea europaea. It has been reported to have a number of pharmacological properties and associated health benefits including anti-inflammatory, anti-atherogenic, anti-cancer, antimicrobial and antiviral activities [3]. Oleuropein and its metabolite hydroxytyrosol have been shown to have strong antimicrobial activity against both Gram-negative and Gram-positive bacteria [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 6
Rotatable bonds 11
Topological polar surface area 201.67
Molecular weight 540.18
XLogP 0.26
No. Lipinski's rules broken 3
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Canonical SMILES OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H](/C/2=C\C)CC(=O)OCCc2ccc(c(c2)O)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Isomeric SMILES OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H](/C/2=C\C)CC(=O)OCCc2ccc(c(c2)O)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1
1. Bisignano G, Tomaino A, Lo Cascio R, Crisafi G, Uccella N, Saija A. (1999)
On the in-vitro antimicrobial activity of oleuropein and hydroxytyrosol.
J Pharm Pharmacol, 51 (8): 971-4. [PMID:10504039]
2. Cui M, Chen B, Xu K, Rigakou A, Diamantakos P, Melliou E, Logothetis DE, Magiatis P. (2021)
Activation of specific bitter taste receptors by olive oil phenolics and secoiridoids.
Sci Rep, 11 (1): 22340. [PMID:34785711]
3. Omar SH. (2010)
Oleuropein in olive and its pharmacological effects.
Sci Pharm, 78 (2): 133-54. [PMID:21179340]