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 15:12:43 UTC |
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Update Date | 2022-03-07 02:49:18 UTC |
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HMDB ID | HMDB0003231 |
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Secondary Accession Numbers | - HMDB0010377
- HMDB03231
- HMDB10377
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Metabolite Identification |
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Common Name | Vaccenic acid |
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Description | Vaccenic acid is a naturally occurring trans fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food. Its IUPAC name is (11E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow). Vaccenic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Vaccenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. |
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Structure | CCCCCC\C=C\CCCCCCCCCC(O)=O InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+ |
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Synonyms | Value | Source |
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(11E)-Octadecenoic acid | ChEBI | (e)-11-Octadecenoic acid | ChEBI | 11(e)-Vaccenic acid | ChEBI | 18:1 trans-11 | ChEBI | C18:1 trans-11 | ChEBI | Octadec-11(e)-enoic acid | ChEBI | trans-11-Octadecenoic acid | ChEBI | trans-11-Octadecensaeure | ChEBI | trans-Octadec-11-enoic acid | ChEBI | TVA | ChEBI | (11E)-Octadecenoate | Generator | (e)-11-Octadecenoate | Generator | 11(e)-Vaccenate | Generator | Octadec-11(e)-enoate | Generator | trans-11-Octadecenoate | Generator | trans-Octadec-11-enoate | Generator | Vaccenate | Generator | (e)-Octadec-11-enoate | HMDB | 11-Octadecenoic acid, (e)-isomer | HMDB | 11-Octadecenoic acid | HMDB | trans-Vaccenic acid | HMDB | FA(18:1(11Z)) | HMDB | FA(18:1n7) | HMDB | Vaccenic acid | ChEBI |
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Chemical Formula | C18H34O2 |
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Average Molecular Weight | 282.468 |
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Monoisotopic Molecular Weight | 282.255880335 |
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IUPAC Name | (11E)-octadec-11-enoic acid |
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Traditional Name | trans-vaccenic acid |
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CAS Registry Number | 693-72-1 |
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SMILES | CCCCCC\C=C\CCCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+ |
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InChI Key | UWHZIFQPPBDJPM-BQYQJAHWSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Long-chain fatty acid
- Unsaturated fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect
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Adverse health effect
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Disposition
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Biological location
Source
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 44 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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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 SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 177.656 | 30932474 | DeepCCS | [M-H]- | 173.636 | 30932474 | DeepCCS | [M-2H]- | 210.822 | 30932474 | DeepCCS | [M+Na]+ | 186.709 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Vaccenic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0apl-9200000000-f39f178414756ab6ad8a | 2018-05-25 | Not Available | 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 - Vaccenic acid Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-001i-0090000000-dee621bf09f57d88e5ed | 2018-05-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Vaccenic acid Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-001i-9340000000-654e2ea72d5477e26606 | 2018-05-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Vaccenic acid Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-0aou-9000000000-413d3363f22e7baf1df7 | 2018-05-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Vaccenic acid 30V, Positive-QTOF | splash10-001i-0090000000-2a569bab7642a2f75401 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Vaccenic acid 20V, Positive-QTOF | splash10-001i-0090000000-dd6c9ec9fb483004fb56 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Vaccenic acid 10V, Positive-QTOF | splash10-001i-0090000000-6d641aebf861b449bc93 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 10V, Positive-QTOF | splash10-014i-0090000000-36b21b13adac790098f8 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 20V, Positive-QTOF | splash10-00rj-4490000000-16982dc88f830f9024c2 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 40V, Positive-QTOF | splash10-0096-9830000000-7359fa780da86e1ebab3 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 10V, Negative-QTOF | splash10-001i-0090000000-1b80c5a75129c09b94ae | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 20V, Negative-QTOF | splash10-01qi-0090000000-6bb63cb21fc095c3aa5c | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 40V, Negative-QTOF | splash10-0a4l-9230000000-c86275a736982cfe3139 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 10V, Positive-QTOF | splash10-00lr-4290000000-ef21daa5591bbeb17f87 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 20V, Positive-QTOF | splash10-067j-9310000000-8cc733ca58b618258ca0 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 40V, Positive-QTOF | splash10-0aou-9000000000-60e1d3c5c8de0e9f209c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 10V, Negative-QTOF | splash10-001i-0090000000-8b8562cadde7e7a8ba4f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 20V, Negative-QTOF | splash10-01q9-1090000000-827ccf4b0fb321cd543d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Vaccenic acid 40V, Negative-QTOF | splash10-0006-9220000000-9024da2ccb79132d937a | 2021-09-24 | 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, CDCl3, experimental) | 2018-05-25 | Wishart Lab | View Spectrum |
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Disease References | 11-beta-Hydroxylase deficiency |
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- Psychogios N, Hau DD, Peng J, Guo AC, Mandal R, Bouatra S, Sinelnikov I, Krishnamurthy R, Eisner R, Gautam B, Young N, Xia J, Knox C, Dong E, Huang P, Hollander Z, Pedersen TL, Smith SR, Bamforth F, Greiner R, McManus B, Newman JW, Goodfriend T, Wishart DS: The human serum metabolome. PLoS One. 2011 Feb 16;6(2):e16957. doi: 10.1371/journal.pone.0016957. [PubMed:21359215 ]
- Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
| Isovaleric acidemia |
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- Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
| Obesity |
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- Haro C, Montes-Borrego M, Rangel-Zuniga OA, Alcala-Diaz JF, Gomez-Delgado F, Perez-Martinez P, Delgado-Lista J, Quintana-Navarro GM, Tinahones FJ, Landa BB, Lopez-Miranda J, Camargo A, Perez-Jimenez F: Two Healthy Diets Modulate Gut Microbial Community Improving Insulin Sensitivity in a Human Obese Population. J Clin Endocrinol Metab. 2016 Jan;101(1):233-42. doi: 10.1210/jc.2015-3351. Epub 2015 Oct 27. [PubMed:26505825 ]
| 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 ]
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