| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:29 UTC |
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| Update date | 2019-11-26 03:07:54 UTC |
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| Primary ID | FDB013034 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Oleanolic acid |
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| Description | Occurs 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. |
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| CAS Number | 508-02-1 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| 3beta-Hydroxyolean-12-en-28-Oic acid | ChEBI | | Astrantiagenin C | ChEBI | | Caryophyllin | ChEBI | | Giganteumgenin C | ChEBI | | Oleanic acid | ChEBI | | Virgaureagenin b | ChEBI | | Oleanolate | Kegg | | 3b-Hydroxyolean-12-en-28-Oate | Generator | | 3b-Hydroxyolean-12-en-28-Oic acid | Generator | | 3beta-Hydroxyolean-12-en-28-Oate | Generator | | 3Β-hydroxyolean-12-en-28-Oate | Generator | | 3Β-hydroxyolean-12-en-28-Oic acid | Generator | | Oleanate | Generator | | (3-beta)-3-Hydroxyolean-12-en-28-Oate | HMDB | | (3-beta)-3-Hydroxyolean-12-en-28-Oic acid | HMDB | | (3.beta.)-3-beta-hydroxy-olean-12-en-28-Oate | HMDB | | (3.beta.)-3-beta-hydroxy-olean-12-en-28-Oic acid | HMDB | | (3.beta.)-3-hydroxy-olean-12-en-28-Oate | HMDB | | (3.beta.)-3-hydroxy-olean-12-en-28-Oic acid | HMDB | | (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 acid | HMDB | | 3-beta-Hydroxyolean-12-en-28-Oate | HMDB | | 3-beta-Hydroxyolean-12-en-28-Oic acid | HMDB | | 3.beta.-hydroxy-olean-12-en-28-Oate | HMDB | | 3.beta.-hydroxy-olean-12-en-28-Oic acid | HMDB | | 3beta-Hydroxy-olean-12-en-28-Oate | HMDB | | 3beta-Hydroxy-olean-12-en-28-Oic acid | HMDB | | Oleanane triterpenes | HMDB | | Triterpenes, oleanane | HMDB | | Oleanol | HMDB | | Hederins | HMDB | | (+)-Oleanolic acid | manual | | (3-beta)-3-Hydroxyolean-12-en-28-oate | biospider | | (3-beta)-3-Hydroxyolean-12-en-28-oic acid | biospider | | (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 acid | HMDB | | 3-beta-Hydroxyolean-12-en-28-oate | biospider | | 3-beta-Hydroxyolean-12-en-28-oic acid | biospider | | 3β-hydroxyolean-12-en-28-Oate | Generator | | 3β-hydroxyolean-12-en-28-Oic acid | Generator | | Gledigenin 1 | db_source | | Olean-12-en-28-oic acid, 3-beta-hydroxy- (8CI) | biospider | | Olean-12-en-28-oic acid, 3-hydroxy-, (3-beta)- | biospider | | Olean-12-en-28-oic acid, 3-hydroxy-, (3β)- | biospider | | Olean-12-en-28-oic acid, 3β-hydroxy- | biospider | | Olean-12-en-28-oic acid, 3beta-hydroxy- (8CI) | biospider | | Oleanolic acid | db_source | | Virgaureagenin B | db_source |
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| Predicted Properties | |
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| Chemical Formula | C30H48O3 |
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| IUPAC name | (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 acid |
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| InChI Identifier | InChI=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/s1 |
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| InChI Key | MIJYXULNPSFWEK-GTOFXWBISA-N |
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| Isomeric SMILES | CC1(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)=O |
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| Average Molecular Weight | 456.711 |
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| Monoisotopic Molecular Weight | 456.360345406 |
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| Classification |
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| Description | belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Triterpenoids |
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| Direct Parent | Triterpenoids |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Industrial application: Biological role: |
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| Foods | Fats and oils: |
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| Physico-Chemical Properties - Experimental |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 78.90%; H 10.59%; O 10.51% | DFC |
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| Melting Point | Mp 306-308° | DFC |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | [a]12D +79.5 (CHCl3) | DFC |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0udi-2951000000-3ffcf6404c28c9072e6e | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0udi-2951000000-3ffcf6404c28c9072e6e | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002f-0014900000-844b76f23b4a02a75c20 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-000i-1011190000-4d07cbb48cd57a724a3c | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative | splash10-0a4i-0000900002-a0a4b7ccad94baf5df67 | JSpectraViewer | MoNA | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-052r-0001900000-948551e80a675e804945 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01vx-0116900000-a7bbd734cfb389f003ce | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001l-3459300000-fe5b4ff0a697d946a205 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000900000-24b5f92b17a675bd0042 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08fu-0003900000-df302b7b4b1f9bf77cc5 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000e-2007900000-2e9882aa899cbe3bd6da | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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| External Links |
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| ChemSpider ID | 10062 |
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| ChEMBL ID | CHEMBL168 |
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| KEGG Compound ID | C17148 |
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| Pubchem Compound ID | 10494 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 37659 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB02364 |
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| CRC / DFC (Dictionary of Food Compounds) ID | KMF67-H:HNW57-L |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | OLEANOLIC-ACID|BETA-OLEANOLIC-ACID |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00019064 |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Oleanolic_acid |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| abortifacient | 50691 | A chemical substance that interrupts pregnancy after implantation. | DUKE | | anti allergic | 50857 | A drug used to treat allergic reactions. | 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 atherosclerotic | 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 bacterial | 33282 | A substance that kills or slows the growth of bacteria. | 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 complement | | | DUKE | | anti edemic | | | DUKE | | anti fertility | | | DUKE | | anti gingivitic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti hepatotoxic | 62868 | Any compound that is able to prevent damage to the liver. | 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 ischemic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti leukemic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti leukotriene | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | anti malarial | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti nephritic | 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 periodontic | | | DUKE | | anti peroxidant | | | DUKE | | anti prostaglandin-E2 | 49023 | A compound that inhibits the action of prostaglandins. | DUKE | | anti plaque | | | DUKE | | anti plasmodial | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti sarcomic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti TGF-beta | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | antitumor | 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 | | 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 | | 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 | | 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 | | hypolipemic | | | 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 | | NF-kappa-B inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | phagocytotic | | | DUKE | | piscicide | | | DUKE | | prostaglandin synthesis inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | sedative | 35717 | A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. | DUKE | | utero tonic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | vasopressor | | | DUKE |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| 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.
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