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CHEBI:139162 - oleuropein aglycone

Default Structure
ChEBI IDCHEBI:139162
ChEBI Nameoleuropein aglycone
Stars
DefinitionA secoiridoid that is the methyl ester of 3,4-dihydro-2H-pyran-5-carboxylic acid which is substituted at positions 2, 3, and 4 by hydroxy, ethylidene, and carboxymethyl groups, respectively and in which the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2R,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.
Last Modified31 January 2018
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC19H22O8
Net Charge0
Average Mass378.377
Monoisotopic Mass378.13147
SMILES[H][C@@]1(CC(=O)OCCc2ccc(O)c(O)c2)C(C(=O)OC)=CO[C@@H](O)/C1=C/C
InChIInChI=1S/C19H22O8/c1-3-12-13(14(18(23)25-2)10-27-19(12)24)9-17(22)26-7-6-11-4-5-15(20)16(21)8-11/h3-5,8,10,13,19-21,24H,6-7,9H2,1-2H3/b12-3+/t13-,19+/m0/s1
InChIKeyBIWKXNFEOZXNLX-BBHIFXBUSA-N
Species of MetaboliteComponentSourceComments
Olea europaea (ncbitaxon:4146) - PubMed (21411195)
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
TRPA1 channel agonist  An agonist at the transient receptor potential cation channel A1 (TRPA1).
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
mTOR inhibitor  A protein kinase inhibitor of the mammalian target of rapamycin (mTOR), a protein that regulates cell growth, cell proliferation, cell motility, cell survival, protein synthesis and transcription. mTOR inhibitors are used to prevent transplant rejection and in treatment of cancer.
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
oleuropein aglycone (CHEBI:139162) has functional parent oleuropein (CHEBI:7747)
oleuropein aglycone (CHEBI:139162) has role anti-inflammatory agent (CHEBI:67079)
oleuropein aglycone (CHEBI:139162) has role antioxidant (CHEBI:22586)
oleuropein aglycone (CHEBI:139162) has role mTOR inhibitor (CHEBI:68481)
oleuropein aglycone (CHEBI:139162) has role neuroprotective agent (CHEBI:63726)
oleuropein aglycone (CHEBI:139162) has role plant metabolite (CHEBI:76924)
oleuropein aglycone (CHEBI:139162) has role TRPA1 channel agonist (CHEBI:137514)
oleuropein aglycone (CHEBI:139162) is a catechols (CHEBI:33566)
oleuropein aglycone (CHEBI:139162) is a diester (CHEBI:51307)
oleuropein aglycone (CHEBI:139162) is a lactol (CHEBI:38131)
oleuropein aglycone (CHEBI:139162) is a methyl ester (CHEBI:25248)
oleuropein aglycone (CHEBI:139162) is a pyrans (CHEBI:26407)
oleuropein aglycone (CHEBI:139162) is a secoiridoid (CHEBI:139166)
IUPAC Name 
methyl (2R,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-hydroxy-3,4-dihydro-2H-pyran-5-carboxylate
UniProt Name  Source
oleuropein aglyconeUniProt
Manual XrefsDatabases
CPD-20219MetaCyc
HMDB0029304HMDB
Registry NumbersSources
Reaxys:8397738Reaxys
CAS:31773-95-2ChemIDplus
Citations