Record Information |
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Version | 5.0 |
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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 | 2022-03-07 02:49:15 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 | [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 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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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 | MeSH, HMDB | Triterpenes, oleanane | MeSH, HMDB | Oleanol | MeSH, HMDB | Hederins | MeSH, 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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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Oleanolic acid,1TMS,isomer #1 | CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1 | 3725.7 | Semi standard non polar | 33892256 | Oleanolic acid,1TMS,isomer #2 | CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1 | 3618.0 | Semi standard non polar | 33892256 | Oleanolic acid,2TMS,isomer #1 | CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1 | 3591.4 | Semi standard non polar | 33892256 | Oleanolic acid,1TBDMS,isomer #1 | CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1 | 3953.4 | Semi standard non polar | 33892256 | Oleanolic acid,1TBDMS,isomer #2 | CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1 | 3887.1 | Semi standard non polar | 33892256 | Oleanolic acid,2TBDMS,isomer #1 | CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1 | 4090.1 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Oleanolic acid GC-MS (2 TMS) | splash10-0udi-2951000000-3ffcf6404c28c9072e6e | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Oleanolic acid GC-MS (Non-derivatized) | splash10-0udi-2951000000-3ffcf6404c28c9072e6e | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Oleanolic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-002f-0014900000-844b76f23b4a02a75c20 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Oleanolic acid GC-MS (2 TMS) - 70eV, Positive | splash10-000i-1011190000-4d07cbb48cd57a724a3c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Oleanolic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Oleanolic acid LC-ESI-ITTOF (LCMS-IT-TOF) , Negative-QTOF | splash10-0a4i-0000900002-a0a4b7ccad94baf5df67 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Oleanolic acid 50V, Negative-QTOF | splash10-0a4i-0000900000-bc55e4c6ed84a38ec6a8 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Oleanolic acid 40V, Negative-QTOF | splash10-0a4i-0000900000-6a5c27def3e5639abbbc | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Oleanolic acid 30V, Negative-QTOF | splash10-0a4i-0000900000-62f98aa71d39d7185d67 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Oleanolic acid 10V, Negative-QTOF | splash10-0a4i-0000900000-0492f069e415506430f0 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Oleanolic acid 20V, Negative-QTOF | splash10-0a4i-0000900000-09b6dab9027bd312a816 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 10V, Positive-QTOF | splash10-052r-0001900000-948551e80a675e804945 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 20V, Positive-QTOF | splash10-01vx-0116900000-a7bbd734cfb389f003ce | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 40V, Positive-QTOF | splash10-001l-3459300000-fe5b4ff0a697d946a205 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 10V, Negative-QTOF | splash10-0a4i-0000900000-24b5f92b17a675bd0042 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 20V, Negative-QTOF | splash10-08fu-0003900000-df302b7b4b1f9bf77cc5 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 40V, Negative-QTOF | splash10-000e-2007900000-2e9882aa899cbe3bd6da | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 10V, Negative-QTOF | splash10-0a4i-0000900000-0d11296813b631a2140f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 20V, Negative-QTOF | splash10-0a4i-0000900000-a04074ef438068f127bb | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 40V, Negative-QTOF | splash10-0a4i-0001900000-ec650846439f5cbbb4c2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 10V, Positive-QTOF | splash10-0a4i-0000900000-a2106bcf05d5c3dc7def | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 20V, Positive-QTOF | splash10-052r-0694700000-aa642e480c6b2dafc5d5 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleanolic acid 40V, Positive-QTOF | splash10-00ei-0940000000-67c9b141383d1a95ec29 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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