| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation date | 2010-04-08 22:11:14 UTC |
|---|
| Update date | 2019-11-26 03:09:56 UTC |
|---|
| Primary ID | FDB014373 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Chemical Information |
|---|
| FooDB Name | Ursolic acid |
|---|
| Description | 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. |
|---|
| CAS Number | 77-52-1 |
|---|
| Structure | |
|---|
| Synonyms | | Synonym | Source |
|---|
| Ursolate | Generator | | .beta.-ursolic acid | HMDB | | (3 beta)-3-hydroxyurs-12-en-28-oic acid | biospider | | (3b)-3-Hydroxyurs-12-en-28-Oate | Generator | | (3b)-3-Hydroxyurs-12-en-28-Oic acid | Generator | | (3beta)-3-hydroxy-Urs-12-en-28-oate | biospider | | (3beta)-3-hydroxy-Urs-12-en-28-oic acid | biospider | | (3beta)-3-Hydroxyurs-12-en-28-oate | biospider | | (3beta)-3-Hydroxyurs-12-en-28-oic acid | biospider | | (3β)-3-hydroxyurs-12-en-28-Oate | Generator | | (3β)-3-hydroxyurs-12-en-28-Oic acid | Generator | | β-ursolic acid | biospider | | 3-epi-ursolic acid | biospider | | 3.beta.-hydroxy-urs-12-en-28-Oate | HMDB | | 3.beta.-hydroxy-urs-12-en-28-Oic acid | HMDB | | 3beta-Hydroxy-12-ursen-28-ic acid | biospider | | 3beta-hydroxy-Urs-12-en-28-oate | biospider | | 3beta-hydroxy-Urs-12-en-28-oic acid | biospider | | 3beta-Hydroxyurs-12-en-28-oate | biospider | | 3beta-Hydroxyurs-12-en-28-oic acid | biospider | | Bungeolic acid | db_source | | Formosolic acid | db_source | | Forucosolic acid | db_source | | Malol | db_source | | Merotaine | biospider | | Micromerol | db_source | | Prunol | db_source | | Urs-12-en-28-oic acid, 3-hydroxy-, (3β)- | biospider | | Urs-12-en-28-oic acid, 3-hydroxy-, (3beta)- | biospider | | Urs-12-en-28-oic acid, 3β-hydroxy- | biospider | | Urs-12-en-28-oic acid, 3beta-hydroxy- | biospider | | Urs-12-en-28-oic acid, 3beta-hydroxy- (8CI) | biospider | | Ursolic acid | db_source | | Urson | db_source |
|
|---|
| Predicted Properties | |
|---|
| Chemical Formula | C30H48O3 |
|---|
| IUPAC name | (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 |
|---|
| InChI Identifier | 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 |
|---|
| InChI Key | WCGUUGGRBIKTOS-JJWDWEPMSA-N |
|---|
| Isomeric 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 |
|---|
| Average Molecular Weight | 456.7003 |
|---|
| Monoisotopic Molecular Weight | 456.360345402 |
|---|
| Classification |
|---|
| Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Prenol lipids |
|---|
| Sub Class | Triterpenoids |
|---|
| Direct Parent | Triterpenoids |
|---|
| Alternative Parents | |
|---|
| Substituents | - Triterpenoid
- Cyclic alcohol
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homopolycyclic compound
|
|---|
| Molecular Framework | Aliphatic homopolycyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Ontology |
|---|
| Ontology | No ontology term |
|---|
| Physico-Chemical Properties - Experimental |
|---|
| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
|---|
| Physical state | Solid | |
|---|
| Physical Description | Not Available | |
|---|
| Mass Composition | C 78.90%; H 10.59%; O 10.51% | DFC |
|---|
| Melting Point | Mp 291° | DFC |
|---|
| Boiling Point | Not Available | |
|---|
| Experimental Water Solubility | Not Available | |
|---|
| Experimental logP | Not Available | |
|---|
| Experimental pKa | Not Available | |
|---|
| Isoelectric point | Not Available | |
|---|
| Charge | Not Available | |
|---|
| Optical Rotation | [a]D +66 (EtOH) | DFC |
|---|
| Spectroscopic UV Data | Not Available | |
|---|
| Density | Not Available | |
|---|
| Refractive Index | Not Available | |
|---|
|
|---|
| Spectra |
|---|
| Spectra | |
|---|
| EI-MS/GC-MS | Not Available |
|---|
| MS/MS | | Type | Description | Splash Key | View |
|---|
| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-052r-0001900000-147d46bee2af34cb0e9e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01vx-1005900000-1032db86d8a91ecc2551 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-055f-9468500000-8b9923090e53d44a56bf | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000900000-018366f20c7fedd5f9d2 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08fu-0003900000-ef66d040d6b775abb94e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0005-2008900000-0691b4da8771672d1def | 2016-08-03 | View Spectrum |
|
|---|
| NMR | Not Available |
|---|
| External Links |
|---|
| ChemSpider ID | 58472 |
|---|
| ChEMBL ID | CHEMBL169 |
|---|
| KEGG Compound ID | C08988 |
|---|
| Pubchem Compound ID | 64945 |
|---|
| Pubchem Substance ID | Not Available |
|---|
| ChEBI ID | 9908 |
|---|
| Phenol-Explorer ID | Not Available |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | HMDB02395 |
|---|
| CRC / DFC (Dictionary of Food Compounds) ID | JFD04-U:JPW48-T |
|---|
| EAFUS ID | Not Available |
|---|
| Dr. Duke ID | URSOLIC-ACID|BETA-URSOLIC-ACID|URSOLIC-ACID-I|URSOLIC-ACID-II |
|---|
| BIGG ID | Not Available |
|---|
| KNApSAcK ID | C00003558 |
|---|
| HET ID | Not Available |
|---|
| Food Biomarker Ontology | Not Available |
|---|
| VMH ID | Not Available |
|---|
| Flavornet ID | Not Available |
|---|
| GoodScent ID | Not Available |
|---|
| SuperScent ID | Not Available |
|---|
| Wikipedia ID | Ursolic acid |
|---|
| Phenol-Explorer Metabolite ID | Not Available |
|---|
| Duplicate IDS | Not Available |
|---|
| Old DFC IDS | Not Available |
|---|
| Associated Foods |
|---|
| Food | Content Range | Average | Reference |
|---|
| Food | | | Reference |
|---|
|
| Biological Effects and Interactions |
|---|
| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
|---|
| analgesic | 35480 | 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. | DUKE | | anti Alzheimeran | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti arrhythmic | 38070 | 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. | DUKE | | anti arthritic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | anti cancer | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti carcinomic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti cariogenic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti cholestatic | | | DUKE | | anti complement | | | DUKE | | anti diabetic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti Epstein-Barr virus | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anti edemic | | | DUKE | | anti escherichic | | | DUKE | | anti fibrosarcomic | | | DUKE | | anti hepatotoxic | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | | anti histaminic | 37956 | Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. | DUKE | | anti HIV | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anti hyperlipidemic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | | anti leishmanic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti leukemic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti lymphomic | | | DUKE | | anti malarial | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti metastatic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti mutagenic | | | DUKE | | anti nephritic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti obesity | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | antioxidant | 22586 | 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. | DUKE | | anti peroxidant | | | DUKE | | anti plasmodial | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti proliferative | | | DUKE | | anti staphylococcic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | anti TGF-beta | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | anti thromboxane | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | anti trypanosomic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | antitumor promoter | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti ulcer | 49201 | One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. | DUKE | | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | aromatase inhibitor | 50790 | 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. | DUKE | | beta-blocker | | | DUKE | | beta-glucuronidase inhibitor | 23924 | 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. | DUKE | | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | candidicide | | | DUKE | | cardioprotective | 38070 | 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. | DUKE | | cardiotonic | 38070 | 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. | DUKE | | choleretic | | | DUKE | | central nervous system depressant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | | cyclooxygenase-2 inhibitor | 50629 | A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. | DUKE | | cyclooxygenase inhibitor | 35544 | 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. | DUKE | | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | | diuretic | 35498 | An agent that promotes the excretion of urine through its effects on kidney function. | DUKE | | elastase inhibitor | 23924 | 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. | DUKE | | hepatoprotective | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | | hypoglycemic | 35526 | A drug which lowers the blood glucose level. | DUKE | | hypotensive | | | DUKE | | immunomodulator | 50846 | Biologically active substance whose activity affects or plays a role in the functioning of the immune system. | DUKE | | leucocytogenic | | | DUKE | | lipoxygenase inhibitor | 35856 | 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. | DUKE | | matrix-metalloproteinase-9 inhibitor | 50664 | | DUKE | | ornithine-decarboxylase inhibitor | 23924 | 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. | DUKE | | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | | piscicide | | | DUKE | | potassium-sparing | | | DUKE | | protease inhibitor | 37670 | A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases). | DUKE | | protisticide | | | DUKE | | quinone-reductase inducer | | | DUKE | | sodium-sparing | | | DUKE | | topoisomerase-II inhibitor | 50750 | 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. | DUKE | | trypanocide | | | DUKE | | vasopressor | | | DUKE |
|
|---|
| Enzymes | Not Available |
|---|
| Pathways | Not Available |
|---|
| Metabolism | Not Available |
|---|
| Biosynthesis | Not Available |
|---|
| Organoleptic Properties |
|---|
| Flavours | Not Available |
|---|
| Files |
|---|
| MSDS | show |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| General Reference | Not Available |
|---|
| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
|
|---|
