CHEBI:7747 - oleuropein

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ChEBI Name oleuropein
ChEBI ID CHEBI:7747
Definition A secoiridoid glycoside 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 anomeric hydroxy group at position 2 has been converted into its β-D-glucoside and the carboxylic acid moiety of the carboxymethyl substituent has been converted to the corresponding 3,4-dihydroxyphenethyl ester (the 2S,3E,4S stereoisomer). The most important phenolic compound present in olive cultivars.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:68987
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Formula C25H32O13
Net Charge 0
Average Mass 540.515
Monoisotopic Mass 540.18429
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
InChIKey RFWGABANNQMHMZ-ZCHJGGQASA-N
SMILES [C@@H]1([C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O[C@H]2/C(/[C@](C(=CO2)C(=O)OC)([H])CC(=O)OCCC=3C=CC(=C(C3)O)O)=C/C
Metabolite of Species Details
Olea europaea (NCBI:txid4146) Found in leaf (BTO:0000713). Found particularly in leaves, bark and branches See: PubMed
Olea europaea (NCBI:txid4146) Found in leaf (BTO:0000713). Methanolic and aqueous extract of dried olive leaves See: PubMed
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
NF-kappaB inhibitor
An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing oleuropein (CHEBI:7747) has role anti-inflammatory agent (CHEBI:67079)
oleuropein (CHEBI:7747) has role antihypertensive agent (CHEBI:35674)
oleuropein (CHEBI:7747) has role antineoplastic agent (CHEBI:35610)
oleuropein (CHEBI:7747) has role antioxidant (CHEBI:22586)
oleuropein (CHEBI:7747) has role apoptosis inducer (CHEBI:68495)
oleuropein (CHEBI:7747) has role NF-κB inhibitor (CHEBI:73240)
oleuropein (CHEBI:7747) has role nutraceutical (CHEBI:50733)
oleuropein (CHEBI:7747) has role plant metabolite (CHEBI:76924)
oleuropein (CHEBI:7747) has role radical scavenger (CHEBI:48578)
oleuropein (CHEBI:7747) is a β-D-glucoside (CHEBI:22798)
oleuropein (CHEBI:7747) is a catechols (CHEBI:33566)
oleuropein (CHEBI:7747) is a diester (CHEBI:51307)
oleuropein (CHEBI:7747) is a methyl ester (CHEBI:25248)
oleuropein (CHEBI:7747) is a pyrans (CHEBI:26407)
oleuropein (CHEBI:7747) is a secoiridoid glycoside (CHEBI:50274)
Incoming oleuropein aglycone (CHEBI:139162) has functional parent oleuropein (CHEBI:7747)
IUPAC Name
methyl (2S,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate
Synonyms Sources
2-(3,4-dihydroxyphenyl)ethyl (2S-(2α,3E,4β))-3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetate ChemIDplus
[2S-(2α,3E,4β)]-3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetic acid 2-(3,4-dihydroxyphenyl)ethyl ester ChEBI
oleuropein UniProt
Manual Xrefs Databases
C00003093 KNApSAcK
C09794 KEGG COMPOUND
CPD-17784 MetaCyc
FDB014653 FooDB
HMDB0035872 HMDB
Oleuropein Wikipedia
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Registry Numbers Types Sources
32619-42-4 CAS Registry Number KEGG COMPOUND
32619-42-4 CAS Registry Number ChemIDplus
72250 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
28 April 2020
General Comment
2014-10-17 Suggested Classification: ISA:disaccharide(CHEBI:36233); ISA:phenols(CHEBI:33853); ISA:alcohol(CHEBI:30879); ISA:catechols(CHEBI:33566); ISA:oxanes(CHEBI:46942); ISA:ester(CHEBI:35701); ISA:polyol(CHEBI:26191); ISA:secondary alcohol(CHEBI:35681); ISA:monocarboxylic acid(CHEBI:25384); ISA:organonitrogen compound(CHEBI:35352); ISA:acetal(CHEBI:59769); ISA:carbonyl compound(CHEBI:36586); ISA:aromatic alcohol(CHEBI:33854); ISA:primary alcohol(CHEBI:15734);