1.0 2010-04-08 22:11:14 UTC 2019-11-26 03:09:56 UTC FDB014373 Ursolic acid Found in wax of apples, pears and other fruits. V. widely distributed in plants Ursolic acid is a pentacyclic triterpene acid, used in cosmetics, that is also capable of inhibiting various types of cancer cells by inhibiting the STAT3 activation pathway and human fibrosarcoma cells by reducing the expression of matrix metalloproteinase-9 by acting through the glucocorticoid receptor.; Ursolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. Ursolic acid (UA), a pentacyclic triterpene acid, has been isolated from many kinds of medicinal plants, such as Eriobotrya japonica, Rosmarinns officinalis, Melaleuca leucadendron, Ocimum sanctum and Glechoma hederaceae. UA has been reported to produce antitumor activities and antioxidant activity, and is reported to have an antioxidant activity. UA may play an important role in regulating the apoptosis induced by high glucose presumably through scavenging of ROS (reactive oxygen species). It has been found recently that ursolic acid treatment affects growth and apoptosis in cancer cells. (PMID: 15994040, 17516235, 17213663); Ursolic acid is also known as Prunol, Malol, Urson, beta-Ursolic acid, NSC4060, CCRIS 7123, CHEBI:9908, TOS-BB-0966, and 3-Beta-Hydroxy-Urs-12-En-28-Oic Acid. As medicine it is well tolerated and can be used topically and orally. .beta.-ursolic acid (3 beta)-3-hydroxyurs-12-en-28-oic acid (3b)-3-Hydroxyurs-12-en-28-Oate (3b)-3-Hydroxyurs-12-en-28-Oic acid (3beta)-3-hydroxy-Urs-12-en-28-oate (3beta)-3-hydroxy-Urs-12-en-28-oic acid (3beta)-3-Hydroxyurs-12-en-28-oate (3beta)-3-Hydroxyurs-12-en-28-oic acid (3β)-3-hydroxyurs-12-en-28-Oate (3β)-3-hydroxyurs-12-en-28-Oic acid β-ursolic acid 3-epi-ursolic acid 3.beta.-hydroxy-urs-12-en-28-Oate 3.beta.-hydroxy-urs-12-en-28-Oic acid 3beta-Hydroxy-12-ursen-28-ic acid 3beta-hydroxy-Urs-12-en-28-oate 3beta-hydroxy-Urs-12-en-28-oic acid 3beta-Hydroxyurs-12-en-28-oate 3beta-Hydroxyurs-12-en-28-oic acid Bungeolic acid Formosolic acid Forucosolic acid Malol Merotaine Micromerol Prunol Urs-12-en-28-oic acid, 3-hydroxy-, (3β)- Urs-12-en-28-oic acid, 3-hydroxy-, (3beta)- Urs-12-en-28-oic acid, 3β-hydroxy- Urs-12-en-28-oic acid, 3beta-hydroxy- Urs-12-en-28-oic acid, 3beta-hydroxy- (8CI) Ursolate Ursolic acid Urson C30H48O3 456.7003 456.360345402 (1S,2R,4aS,6aS,6bR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,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 acid (1S,2R,4aS,6aS,6bR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid 77-52-1 [H][C@@]12[C@@H](C)[C@H](C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)C3CC[C@@]12C)C(O)=O InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21?,22-,23+,24+,27+,28-,29-,30+/m1/s1 WCGUUGGRBIKTOS-JJWDWEPMSA-N belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Triterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Triterpenoids Aliphatic homopolycyclic compounds Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Triterpenoid Solid logp 6.35 ALOGPS logs -5.89 ALOGPS solubility 5.90e-04 g/l ALOGPS melting_point Mp 291° logp 6.58 ChemAxon pka_strongest_acidic 4.74 ChemAxon pka_strongest_basic -0.84 ChemAxon iupac (1S,2R,4aS,6aS,6bR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,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 acid ChemAxon average_mass 456.7003 ChemAxon mono_mass 456.360345402 ChemAxon smiles [H][C@@]12[C@@H](C)[C@H](C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)C3CC[C@@]12C)C(O)=O ChemAxon formula C30H48O3 ChemAxon inchi InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21?,22-,23+,24+,27+,28-,29-,30+/m1/s1 ChemAxon inchikey WCGUUGGRBIKTOS-JJWDWEPMSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 133.7 ChemAxon polarizability 54.75 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 77628 Specdb::MsMs 77629 Specdb::MsMs 77630 Specdb::MsMs 137802 Specdb::MsMs 137803 Specdb::MsMs 137804 HMDB02395 9908 #<Reference:0x000055ce30aaf3a8> #<Reference:0x000055ce30aaf1f0> #<Reference:0x000055ce30aaf038> American cranberry Type 1 specific Vaccinium macrocarpon 13750 37297.0 37297.0 37297.0 mg/100 g Anatidae Type 1 specific Anatidae 8830 Apple Type 1 specific Malus pumila 283210 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bilberry Type 1 specific Vaccinium myrtillus 180763 250.0 250.0 250.0 mg/100 g Bison Type 1 specific Bison bison 9901 Black elderberry Type 1 specific Sambucus nigra 4202 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Common grape Type 1 specific Vitis vinifera 29760 Common oregano Type 1 specific Origanum vulgare 39352 310.0 310.0 310.0 mg/100 g Common persimmon Type 1 specific Diospyros virginiana 13493 Common sage Type 1 specific Salvia officinalis 38868 73.875 127.75 20.0 mg/100 g Common thyme Type 1 specific Thymus vulgaris 49992 1690.0 1690.0 1690.0 mg/100 g Common verbena Type 1 specific Verbena officinalis 79772 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European cranberry Type 1 specific Vaccinium oxycoccos 516948 0.0 0.0 0.0 European rabbit Type 1 specific Oryctolagus 9984 Fruits Unknown generic Greylag goose Type 1 specific Anser anser 8843 Guava Type 1 specific Psidium guajava 120290 Guinea hen Type 1 specific Numida meleagris 8996 Highbush blueberry Type 1 specific Vaccinium corymbosum 69266 Horse Type 1 specific Equus caballus 9796 Hyssop Type 1 specific Hyssopus officinalis 39324 490.0 490.0 490.0 mg/100 g Jackfruit Type 1 specific Artocarpus heterophyllus 3489 Lemon balm Type 1 specific Melissa officinalis 39338 Loquat Type 1 specific Eriobotrya japonica 32224 Mallard duck Type 1 specific Anas platyrhynchos 8839 Malus (Crab apple) Type 1 specific Malus 3749 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Mustard Type 2 specific Olive Type 1 specific Olea europaea 4146 Ostrich Type 1 specific Struthio camelus 8801 Peach Type 1 specific Prunus persica 3760 Pear Type 1 specific Pyrus communis 23211 Pheasant Type 1 specific Phasianus colchicus 9054 Pomegranate Type 1 specific Punica granatum 22663 525.0 600.0 450.0 mg/100 g Pomes Unknown generic Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Rosemary Type 1 specific Rosmarinus officinalis 39367 1726.0 3450.0 2.0 mg/100 g Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Sour cherry Type 1 specific Prunus cerasus 140311 Spearmint Type 1 specific Mentha spicata 29719 Squab Type 1 specific Columba 8931 Star fruit Type 1 specific Averrhoa carambola 28974 Summer savory Type 1 specific Satureja hortensis 49987 135.0 170.0 100.0 mg/100 g Sweet basil Type 1 specific Ocimum basilicum 39350 85.65 174.0 6.3 mg/100 g Sweet cherry Type 1 specific Prunus avium 42229 Sweet marjoram Type 1 specific Origanum majorana 268884 260.0 260.0 260.0 mg/100 g Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Winter savory Type 1 specific Satureja montana 49988 1600.0 1600.0 1600.0 mg/100 g Analgesic 56 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti carcinomic 162 A substance that inhibits or prevents the proliferation of neoplasms. Anti cariogenic 165 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti complement 200 Anti Epstein-Barr virus 245 A substance that destroys or inhibits replication of viruses. Anti fibrosarcomic 279 Anti hepatotoxic 328 Any compound that is able to prevent damage to the liver. Anti histaminic 331 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. Anti HIV 333 A substance that destroys or inhibits replication of viruses. Anti hyperlipidemic 348 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti leishmanic 388 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti leukemic 393 A substance that inhibits or prevents the proliferation of neoplasms. Anti metastatic 434 A substance that inhibits or prevents the proliferation of neoplasms. Anti nephritic 466 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti peroxidant 519 Anti plasmodial 532 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti TGF-beta 644 A substance that diminishes the rate of a chemical reaction. Anti thromboxane 651 A substance that diminishes the rate of a chemical reaction. Anti trypanosomic 669 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti ulcer 676 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. Anti-Alzheimeran 105 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-arthritic 131 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-cancer 159 A substance that inhibits or prevents the proliferation of neoplasms. Anti-cholestatic 180 Anti-diabetic 228 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-edemic 248 Anti-escherichic 269 Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-lymphomic 414 Anti-malarial 416 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-mutagenic 451 Anti-obesity 486 Any substance introduced into a living organism with therapeutic or diagnostic purpose. 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-proliferative 548 Anti-staphylococcic 627 A substance that kills or slows the growth of bacteria. Anti-viral 689 A substance that destroys or inhibits replication of viruses. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Antitumor promoter 673 A substance that inhibits or prevents the proliferation of neoplasms. Aromatase inhibitor 705 An 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-blocker 728 Beta-glucuronidase inhibitor 729 A 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 preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Candidicide 756 Cardioprotective 769 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. Cardiotonic 771 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. Central nervous system depressant 812 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. Choleretic 801 Cyclooxygenase inhibitor 849 A 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 inhibitor 841 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. Diuretic 883 An agent that promotes the excretion of urine through its effects on kidney function. Elastase inhibitor 897 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Hepatoprotective 981 Any compound that is able to prevent damage to the liver. Hypoglycemic 1017 A drug which lowers the blood glucose level. Hypotensive 1021 Immunomodulator 1031 Biologically active substance whose activity affects or plays a role in the functioning of the immune system. Leucocytogenic 1069 Lipoxygenase inhibitor 1077 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. Matrix-metalloproteinase-9 inhibitor 1112 Ornithine-decarboxylase inhibitor 1175 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Piscicide 1228 Potassium-sparing 1237 Protease inhibitor 1262 A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases). Protisticide 1266 Quinone-reductase inducer 1277 Sodium-sparing 1317 Topoisomerase-II inhibitor 1366 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands. Trypanocide 1384 Vasopressor 1415