1.0 2010-04-08 22:11:23 UTC 2019-11-26 03:10:32 UTC FDB014653 Oleuropein Bitter 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. C25H32O13 540.5138 540.18429111 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 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 32619-42-4 [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=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 RFWGABANNQMHMZ-WLFYAOHHSA-N 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. Terpene glycosides Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene glycosides Aromatic heteromonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Acetals Aromatic monoterpenoids Benzene and substituted derivatives Carbonyl compounds Catechols Dicarboxylic acids and derivatives Enoate esters Hydrocarbon derivatives Iridoids and derivatives Methyl esters Monocyclic monoterpenoids Monosaccharides O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Sugar acids and derivatives Tyrosols and derivatives Vinylogous esters 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Acetal Alcohol Alpha,beta-unsaturated carboxylic ester Aromatic heteromonocyclic compound Aromatic monoterpenoid Benzenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Catechol Dicarboxylic acid or derivatives Enoate ester Glycosyl compound Hydrocarbon derivative Methyl ester Monocyclic benzene moiety Monocyclic monoterpenoid Monosaccharide Monoterpenoid O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Polyol Primary alcohol Secoiridoid-skeleton Secondary alcohol Sugar acid Terpene glycoside Tyrosol derivative Vinylogous ester logp 0.63 ALOGPS logs -2.87 ALOGPS solubility 7.33e-01 g/l ALOGPS melting_point Mp 89-91° logp 0.11 ChemAxon pka_strongest_acidic 4.94 ChemAxon pka_strongest_basic -3 ChemAxon iupac 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 ChemAxon average_mass 540.5138 ChemAxon mono_mass 540.18429111 ChemAxon 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 ChemAxon formula C25H32O13 ChemAxon 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 ChemAxon inchikey RFWGABANNQMHMZ-WLFYAOHHSA-N ChemAxon polar_surface_area 201.67 ChemAxon refractivity 128.22 ChemAxon polarizability 53.4 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 11 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 19415 Specdb::CMs 44613 Specdb::MsMs 49893 Specdb::MsMs 49894 Specdb::MsMs 49895 Specdb::MsMs 115869 Specdb::MsMs 115870 Specdb::MsMs 115871 HMDB35872 #<Reference:0x000055ce30a80be8> #<Reference:0x000055ce30a80738> #<Reference:0x000055ce30a80530> #<Reference:0x000055ce30a800f8> #<Reference:0x000055ce30a7fcc0> Fruits Unknown generic Olive Type 1 specific Olea europaea 4146 31.939616 72.01629982 0.000055 mg/100 g Rape Type 1 specific Brassica napus var. napus 138011 0.0 0.0 0.0 mg/100 g bitter Angiotensin converting enzyme inhibitor 18 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). Anti hypertensive 352 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-arrhythmic 129 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Anti-spasmodic 619 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Bacteristat 725 A substance that kills or slows the growth of bacteria. Coronarydilator 835 Hypotensive 1021 Vasodilator 1413 A drug used to cause dilation of the blood vessels.