CHEBI:85673 - oleocanthal

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ChEBI Name oleocanthal
ChEBI ID CHEBI:85673
Definition A carboxylic ester that is the 2-(p-hydroxyphenyl)ethyl ester of (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid. Oleocanthal is found in olive oil but it is not clear whether the natural product is a mixture of E/Z isomers or a single isomer as the two isomers readily interconvert in solution; most pharmacological studies will have been performed using a mixture.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C17H20O5
Net Charge 0
Average Mass 304.33770
Monoisotopic Mass 304.131
InChI InChI=1S/C17H20O5/c1-2-14(12-19)15(7-9-18)11-17(21)22-10-8-13-3-5-16(20)6-4-13/h2-6,9,12,15,20H,7-8,10-11H2,1H3/t15-/m0/s1
InChIKey VPOVFCBNUOUZGG-HNNXBMFYSA-N
SMILES CC=C(C=O)[C@@H](CC=O)CC(=O)OCCc1ccc(O)cc1
Metabolite of Species Details
Olea europaea (NCBI:txid4146) Found in fruit (BTO:0000486). See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Hsp90 inhibitor
An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing oleocanthal (CHEBI:85673) has functional parent 2-(4-hydroxyphenyl)ethanol (CHEBI:1879)
oleocanthal (CHEBI:85673) has role anti-inflammatory agent (CHEBI:67079)
oleocanthal (CHEBI:85673) has role antineoplastic agent (CHEBI:35610)
oleocanthal (CHEBI:85673) has role antioxidant (CHEBI:22586)
oleocanthal (CHEBI:85673) has role apoptosis inducer (CHEBI:68495)
oleocanthal (CHEBI:85673) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
oleocanthal (CHEBI:85673) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
oleocanthal (CHEBI:85673) has role Hsp90 inhibitor (CHEBI:63962)
oleocanthal (CHEBI:85673) has role neuroprotective agent (CHEBI:63726)
oleocanthal (CHEBI:85673) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
oleocanthal (CHEBI:85673) has role nutraceutical (CHEBI:50733)
oleocanthal (CHEBI:85673) has role plant metabolite (CHEBI:76924)
oleocanthal (CHEBI:85673) is a carboxylic ester (CHEBI:33308)
oleocanthal (CHEBI:85673) is a dialdehyde (CHEBI:38124)
oleocanthal (CHEBI:85673) is a enal (CHEBI:51688)
oleocanthal (CHEBI:85673) is a phenols (CHEBI:33853)
IUPAC Name
2-(4-hydroxyphenyl)ethyl (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoate
Synonyms Sources
(−)-deacetoxy ligstroside aglycon ChEBI
(−)-deacetoxy ligstroside aglycone ChEBI
(−)-oleocanthal ChemIDplus
deacetoxy ligstroside aglycon ChemIDplus
deacetoxy ligstroside aglycone ChEBI
Manual Xrefs Databases
CPD-17783 MetaCyc
Oleocanthal Wikipedia
View more database links
Registry Numbers Types Sources
10180050 Reaxys Registry Number Reaxys
289030-99-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
14 November 2017