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 [2]. Oleuropein and its metabolite hydroxytyrosol have been shown to have strong antimicrobial activity against both Gram-negative and Gram-positive bacteria [1].
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
SMILES / InChI / InChIKey
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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
InChI Key RFWGABANNQMHMZ-ZCHJGGQASA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 707
Other databases
CAS Registry No. 32619-42-4 (source: Scifinder)
ChEBI CHEBI:7747
ChEMBL Ligand CHEMBL1911053
GtoPdb PubChem SID 405560468
PubChem CID 5281544
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Wikipedia Oleuropein