| 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 15:12:43 UTC |
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| Update Date | 2020-02-26 21:24:27 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, also known as 18:1 trans-11 or 11(e)-vaccenate, 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 | |
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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 | | Vaccenic acid | ChEBI | | FA(18:1(11Z)) | HMDB | | FA(18:1n7) | HMDB |
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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 | Health effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Biological role: Industrial application: |
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| Physical Properties |
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| State | Liquid |
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| Experimental 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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| Predicted Properties | |
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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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