oleuropein (CHEBI:7747)

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CHEBI:7747 - oleuropein

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ChEBI ID	CHEBI:7747
ChEBI Name	oleuropein
Stars
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.
Secondary ChEBI ID	CHEBI:68987
Last Modified	28 April 2020
Downloads	Molfile

Formula	C25H32O13
Net Charge	0
Average Mass	540.518
Monoisotopic Mass	540.18429
SMILES	[H][C@@]1(CC(=O)OCCc2ccc(O)c(O)c2)C(C(=O)OC)=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)/C1=C/C
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

Wikipedia

Species of Metabolite	Component	Source	Comments
Olea europaea (ncbitaxon:4146)
	leaf (BTO:0000713)	PubMed (22014168)	Methanolic and aqueous extract of dried olive leaves
	leaf (BTO:0000713)	PubMed (28576392)	Found particularly in leaves, bark and branches

Roles Classification

Chemical Roles:	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. radical scavenger A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Roles:	apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. NF-kappaB inhibitor An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:	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. anti-inflammatory agent Any compound that has anti-inflammatory effects. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	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 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)
	oleuropein (CHEBI:7747) is a β-D-glucoside (CHEBI:22798)
Incoming Relation(s)
Incoming Relation(s)	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	Source
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

UniProt Name	Source
oleuropein	UniProt

Manual Xrefs	Databases
C09794	KEGG COMPOUND
C00003093	KNApSAcK
CPD-17784	MetaCyc
Oleuropein	Wikipedia
HMDB0035872	HMDB
FDB014653	FooDB

Registry Numbers	Sources
Reaxys:72250	Reaxys
CAS:32619-42-4	KEGG COMPOUND
CAS:32619-42-4	ChemIDplus

Citations