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 (28576392)	Found particularly in leaves, bark and branches
	leaf (BTO:0000713)	PubMed (22014168)	Methanolic and aqueous extract of dried olive leaves

Roles Classification

Chemical Roles:	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 Roles:	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. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Applications:	anti-inflammatory agent Any compound that has anti-inflammatory effects. 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. 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.

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

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

Citations