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CHEBI:139162 - oleuropein aglycone

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).
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
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