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Showing Compound Oleuropein (FDB014653)

Record Information
Version1.0
Creation date2010-04-08 22:11:23 UTC
Update date2019-11-26 03:10:32 UTC
Primary IDFDB014653
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameOleuropein
DescriptionBitter principle of olives. Nutriceutical with antioxidant props. 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.
CAS Number32619-42-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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 acidGenerator
OleuropeinMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.73 g/LALOGPS
logP0.63ALOGPS
logP0.11ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.94ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area201.67 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity128.22 m³·mol⁻¹ChemAxon
Polarizability53.4 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC25H32O13
IUPAC namemethyl (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
InChI IdentifierInChI=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 KeyRFWGABANNQMHMZ-WLFYAOHHSA-N
Isomeric 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
Average Molecular Weight540.5138
Monoisotopic Molecular Weight540.18429111
Classification
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTerpene 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 FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Foods

Fats and oils:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.55%; H 5.97%; O 38.48%DFC
Melting PointMp 89-91°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]26D -168 (c, 0.67 in MeOH)DFC
Spectroscopic UV Data326 (E1%/1cm 49) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSOleuropein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0c09-9807550000-77b88c3208433770b81aSpectrum
Predicted GC-MSOleuropein, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0aw9-4770809000-47d809792be9bb073a2dSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0203-0849050000-bc4c5d2612c3a25aa4f52016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0924000000-bfe04edc9fcb703a21e12016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-6195a4c34ddc5a07f2852016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-1529060000-8943dc0f78c01da9825e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-024i-2739120000-261fe969828a9fd9f92f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7987010000-0a65dd0cbf567552b1c12016-08-03View Spectrum
NMRNot Available
ChemSpider ID4444876
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5281544
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID677
DrugBank IDNot Available
HMDB IDHMDB35872
CRC / DFC (Dictionary of Food Compounds) IDJTL00-Y:JTL00-Y
EAFUS IDNot Available
Dr. Duke IDOLEUROPEIN
BIGG IDNot Available
KNApSAcK IDC00003093
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDOleuropein
Phenol-Explorer Metabolite ID677
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Angiotensin converting enzyme inhibitor35457 An agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.DUKE
Anti-arrhythmic38070 An agent that regulates heart rhythm, correcting irregular heartbeat patterns. Therapeutically, it restores normal cardiac function, commonly used to manage arrhythmias, prevent sudden cardiac death, and treat conditions like atrial fibrillation and ventricular tachycardia.DUKE
Anti hypertensive52217 An agent that lowers blood pressure, reducing the risk of cardiovascular disease. It plays a biological role in relaxing blood vessels, decreasing cardiac workload, and improving blood flow. Therapeutically, it's used to manage hypertension, heart failure, and stroke, with key medical applications in preventing organ damage and improving overall cardiovascular health.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Bacteristat33282 An agent that inhibits bacterial growth, reducing the proliferation of microorganisms without killing them. Therapeutically, bacteristats are used to treat infections, preventing the spread of bacteria and allowing the host's immune system to clear the infection. Key medical uses include treating urinary tract infections, acne, and other bacterial infections where bactericidal agents may not be necessary.DUKE
CoronarydilatorAn agent that dilates coronary vessels, increasing blood flow to the heart. Its biological role is to reduce cardiac workload and improve oxygen delivery. Therapeutically, it's used to treat angina, myocardial infarction, and other cardiovascular conditions, improving cardiac function and reducing symptoms.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).