ChemFOnt: Showing chemical card for Oleuropein (CFc000016866)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:06:37 UTC

Chemfont ID

CFc000016866

Molecule Identification

Common Name

Oleuropein

Definition

Oleuropein is found in fruits. Oleuropein is a bitter principle of olives. Nutriceutical with antioxidant properties.Oleuropein is a chemical compound found in olive leaf from the olive tree (and leaves of privet) together with other closely related compounds such as 10-hydroxyoleuropein, ligstroside, and 10-hydroxyligstroside. All these compounds are tyrosol esters of elenolic acid that are further hydroxylated and glycosylated. Oleuropein and its metabolite hydroxytyrosol have powerful antioxidant activity both in vivo and in vitro and give extra-virgin olive oil its bitter, pungent taste. Oleuropein preparations have been claimed to strengthen the immune system

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Methyl (2S,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator
Oleuropein	MeSH

Chemical Formula

C₂₅H₃₂O₁₃

Average Molecular Weight

540.5138

Monoisotopic Molecular Weight

540.18429111

IUPAC Name

methyl (2S,3Z,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl (4S,5Z,6S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethylidene-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

CAS Registry Number

32619-42-4

SMILES

[H][C@]1(CC(=O)OCCC2=CC(O)=C(O)C=C2)\C(=C\C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC

InChI Identifier

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

InChI Key

RFWGABANNQMHMZ-WLFYAOHHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Tyrosol derivative
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Sugar acid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Vinylogous ester
Secondary alcohol
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035872)

Source

Endogenous

Endogenous (HMDB: HMDB0035872)

Plant

Plant (HMDB: HMDB0035872)

Animal

Animal (HMDB: HMDB0035872)

Exogenous

Food

Food (HMDB: HMDB0035872)

Vegetable

Root vegetable

Rape (FooDB: FOOD00029)

Fruit vegetable

Olive (FooDB: FOOD00121)

Fat and oil

Olive oil (HMDB: HMDB0035872)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0035872)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035872)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035872)

Lipid metabolism pathway (HMDB: HMDB0035872)

Cellular process

Cell signaling (HMDB: HMDB0035872)

Biochemical process

Lipid transport (HMDB: HMDB0035872)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.73 g/L	ALOGPS
logP	0.63	ALOGPS
logP	0.11	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.94	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.67 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	128.22 m³·mol⁻¹	ChemAxon
Polarizability	53.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon