1.02010-04-08 22:10:29 UTC2019-11-26 03:07:54 UTCFDB013034Oleanolic acidOccurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone
Oleanolic acid or oleanic acid is a naturally occurring triterpenoid, widely distributed in food and medicinal plants, related to betulinic acid. It can be found in Phytolacca americana (American pokeweed), and Syzygium spp, garlic, etc. It is relatively non-toxic, antitumor, and hepatoprotective, as well as exhibiting antiviral properties. (+)-Oleanolic acid(3-beta)-3-Hydroxyolean-12-en-28-oate(3-beta)-3-Hydroxyolean-12-en-28-oic acid(3.beta.)-3-beta-hydroxy-olean-12-en-28-Oate(3.beta.)-3-beta-hydroxy-olean-12-en-28-Oic acid(3.beta.)-3-hydroxy-olean-12-en-28-Oate(3.beta.)-3-hydroxy-olean-12-en-28-Oic acid(4AS,5S,6as,6br,8R,8ar,10S,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid3-beta-Hydroxyolean-12-en-28-oate3-beta-Hydroxyolean-12-en-28-oic acid3.beta.-hydroxy-olean-12-en-28-Oate3.beta.-hydroxy-olean-12-en-28-Oic acid3b-Hydroxyolean-12-en-28-Oate3b-Hydroxyolean-12-en-28-Oic acid3beta-Hydroxy-olean-12-en-28-Oate3beta-Hydroxy-olean-12-en-28-Oic acid3beta-Hydroxyolean-12-en-28-Oate3beta-Hydroxyolean-12-en-28-Oic acid3β-hydroxyolean-12-en-28-Oate3β-hydroxyolean-12-en-28-Oic acidAstrantiagenin CCaryophyllinGiganteumgenin CGledigenin 1Olean-12-en-28-oic acid, 3-beta-hydroxy- (8CI)Olean-12-en-28-oic acid, 3-hydroxy-, (3-beta)-Olean-12-en-28-oic acid, 3-hydroxy-, (3β)-Olean-12-en-28-oic acid, 3β-hydroxy-Olean-12-en-28-oic acid, 3beta-hydroxy- (8CI)OleanateOleanic acidOleanolic acidVirgaureagenin BC30H48O3456.711456.360345406(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acidoleanolic acid508-02-1CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=OInChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1MIJYXULNPSFWEK-GTOFXWBISA-N belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.TriterpenoidsOrganic compoundsLipids and lipid-like moleculesPrenol lipidsTriterpenoidsAliphatic homopolycyclic compoundsCarbonyl compoundsCarboxylic acidsCyclic alcohols and derivativesHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesSecondary alcoholsAlcoholAliphatic homopolycyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeCyclic alcoholHydrocarbon derivativeMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundSecondary alcoholTriterpenoidOleanane triterpenoidsOleanane triterpenoidsOleananeshydroxy monocarboxylic acidpentacyclic triterpenoidSolidlogp7.09logs-5.75solubility8.17e-04 g/lmelting_pointMp 306-308°logp6.59pka_strongest_acidic4.74pka_strongest_basic-0.84iupac(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acidaverage_mass456.711mono_mass456.360345406smilesCC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=OformulaC30H48O3inchiInChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1inchikeyMIJYXULNPSFWEK-GTOFXWBISA-Npolar_surface_area57.53refractivity133.62polarizability54.87rotatable_bond_count1acceptor_count3donor_count2physiological_charge-1formal_charge0Specdb::NmrTwoD1820Specdb::CMs2331Specdb::CMs10506Specdb::CMs31415Specdb::CMs38393Specdb::CMs160783Specdb::NmrOneD1883Specdb::MsMs6346Specdb::MsMs239683Specdb::MsMs239684Specdb::MsMs239685Specdb::MsMs241738Specdb::MsMs241739Specdb::MsMs241740Specdb::MsMs2245276Specdb::MsMs2249022Specdb::MsMs2249381Specdb::MsMs2251063Specdb::MsMs2251332Specdb::MsMs2302791Specdb::MsMs2302792Specdb::MsMs2302793Specdb::MsMs3066803Specdb::MsMs3066804Specdb::MsMs3066805HMDB0236437659#<Reference:0x0000555675ce6348>#<Reference:0x0000555675ce6190>#<Reference:0x0000555675ce5fd8>American cranberryType 1specificVaccinium macrocarpon13750American pokeweedType 1specificPhytolacca americana3527AnatidaeType 1specificAnatidae8830AppleType 1specificMalus pumila283210BeefaloType 1specificBos taurus X Bison bison297284BilberryType 1specificVaccinium myrtillus180763BisonType 1specificBison bison9901Black elderberryType 1specificSambucus nigra4202BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031ClovesType 1specificSyzygium aromaticum2198681500.02000.01000.0mg/100 gColumbidae (Dove, Pigeon)Type 1specificColumbidae8930Common grapeType 1specificVitis vinifera29760Common oreganoType 1specificOriganum vulgare39352Common sageType 1specificSalvia officinalis3886843.1546.340.0mg/100 gCommon thymeType 1specificThymus vulgaris49992630.0630.0630.0mg/100 gCornType 1specificZea mays4577DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Fats and oilsUnknowngenericFennelType 1specificFoeniculum vulgare48038FigType 1specificFicus carica3494Garden onionType 1specificAllium cepa4679German camomileType 1specificMatricaria recutita127986Greylag gooseType 1specificAnser anser8843GuavaType 1specificPsidium guajava120290Guinea henType 1specificNumida meleagris8996Herbs and SpicesUnknowngenericHighbush blueberryType 1specificVaccinium corymbosum69266HorseType 1specificEquus caballus9796HyssopType 1specificHyssopus officinalis39324Japanese persimmonType 1specificDiospyros kaki35925JujubeType 1specificZiziphus zizyphus48393LambsquartersType 1specificChenopodium album3559Lemon balmType 1specificMelissa officinalis39338LoquatType 1specificEriobotrya japonica32224Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871NutmegType 1specificMyristica fragrans51089OliveType 1specificOlea europaea4146OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054PomegranateType 1specificPunica granatum22663QuailType 1specificPhasianidae9005QuinoaType 1specificChenopodium quinoa63459RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Root vegetablesUnknowngenericRosemaryType 1specificRosmarinus officinalis39367526.01050.02.0mg/100 gSaffronType 1specificCrocus sativus82528Sheep (Mutton, Lamb)Type 1specificOvis aries9940Soft-necked garlicType 1specificAllium sativum L. var. sativum4682Sour cherryType 1specificPrunus cerasus140311SpearmintType 1specificMentha spicata29719SquabType 1specificColumba8931Summer savoryType 1specificSatureja hortensis4998760.060.060.0mg/100 gSunflowerType 1specificHelianthus annuus4232Sweet basilType 1specificOcimum basilicum39350130.0130.0130.0mg/100 gSweet cherryType 1specificPrunus avium42229Sweet marjoramType 1specificOriganum majorana268884470.0470.0470.0mg/100 gTowel gourdType 1specificLuffa aegyptiaca3670TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Winter savoryType 1specificSatureja montana49988abortifacient13A chemical substance that interrupts pregnancy after implantation.anti allergic103A drug used to treat allergic reactions.anti arrhythmic129A 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 atherosclerotic138A 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 bacterial145A substance that kills or slows the growth of bacteria.anti carcinomic162A substance that inhibits or prevents the proliferation of neoplasms.anti cariogenic165Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti complement200anti edemic248anti fertility276anti gingivitic298Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti hepatotoxic328Any compound that is able to prevent damage to the liver.anti HIV333A substance that destroys or inhibits replication of viruses.anti hyperlipidemic348Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti inflammatory370A substance that reduces or suppresses inflammation.anti ischemic377Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti leukemic393A substance that inhibits or prevents the proliferation of neoplasms.anti leukotriene399A substance that diminishes the rate of a chemical reaction.anti malarial416A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anti nephritic466Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti periodontic515anti peroxidant519anti plaque531anti plasmodial532A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anti prostaglandin-E2525A compound that inhibits the action of prostaglandins.anti sarcomic592A substance that inhibits or prevents the proliferation of neoplasms.anti septic603A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anti TGF-beta644A substance that diminishes the rate of a chemical reaction.anti ulcer676One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.anti viral689A substance that destroys or inhibits replication of viruses.antioxidant502A 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.antitumor672A substance that inhibits or prevents the proliferation of neoplasms.aromatase inhibitor705An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.beta-blocker728beta-glucuronidase inhibitor729A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.cancer preventive754A substance that inhibits or prevents the proliferation of neoplasms.cardioprotective769A 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.cardiotonic771A 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.cyclooxygenase inhibitor849A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.cyclooxygenase-2 inhibitor841A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.diuretic883An agent that promotes the excretion of urine through its effects on kidney function.elastase inhibitor897A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.hepatoprotective981Any compound that is able to prevent damage to the liver.hypolipemic1019hypotensive1021immunomodulator1031Biologically active substance whose activity affects or plays a role in the functioning of the immune system.leucocytogenic1069NF-kappa-B inhibitor1164A substance that diminishes the rate of a chemical reaction.phagocytotic1212piscicide1228prostaglandin synthesis inhibitor1258A substance that diminishes the rate of a chemical reaction.sedative1311A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.utero tonic1405Any substance introduced into a living organism with therapeutic or diagnostic purpose.vasopressor1415