Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:17:50 UTC |
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Update Date | 2020-11-09 23:16:47 UTC |
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HMDB ID | HMDB0002364 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Oleanolic acid |
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Description | Oleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic 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. (PMID: 17292619 , 15522132 , 15994040 ). |
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Structure | |
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Synonyms | Value | 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 | (3beta)-3-Hydroxyolean-12-en-28-oic acid | PhytoBank | (3β)-3-Hydroxyolean-12-en-28-oic acid | PhytoBank | (+)-Oleanolic acid | PhytoBank | Gledigenin 1 | PhytoBank | Oleonolic acid | PhytoBank | OA | PhytoBank |
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Chemical Formula | C30H48O3 |
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Average Molecular Weight | 456.711 |
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Monoisotopic Molecular Weight | 456.360345406 |
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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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Traditional Name | oleanolic acid |
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CAS Registry Number | 508-02-1 |
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SMILES | [H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O |
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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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Chemical Taxonomy |
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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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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 310 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0udi-2951000000-3ffcf6404c28c9072e6e | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0udi-2951000000-3ffcf6404c28c9072e6e | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002f-0014900000-844b76f23b4a02a75c20 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-000i-1011190000-4d07cbb48cd57a724a3c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative | splash10-0a4i-0000900002-a0a4b7ccad94baf5df67 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-052r-0001900000-948551e80a675e804945 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01vx-0116900000-a7bbd734cfb389f003ce | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001l-3459300000-fe5b4ff0a697d946a205 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000900000-24b5f92b17a675bd0042 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08fu-0003900000-df302b7b4b1f9bf77cc5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000e-2007900000-2e9882aa899cbe3bd6da | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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