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 15:12:12 UTC |
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Update Date | 2022-03-07 02:49:17 UTC |
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HMDB ID | HMDB0002823 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Docosatrienoic acid |
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Description | Docosatrienoic acid, also known as docosatrienoate, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Docosatrienoic acid is a very hydrophobic molecule, is practically insoluble (in water), and is relatively neutral. Application of docosatrienoic acid was shown to dose-dependently decrease the peak K+ current amplitude and accelerate the potassium activation and inactivation kinetics at all membrane potentials. |
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Structure | CC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O InChI=1S/C22H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10H,2,5,8,11-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9- |
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Synonyms | Value | Source |
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(13Z,16Z,19Z) Docosatrienoic acid | ChEBI | all-cis-13,16,19 Docosatrienoic acid | ChEBI | (13Z,16Z,19Z) Docosatrienoate | Generator | all-cis-13,16,19 Docosatrienoate | Generator | Docosatrienoate | Generator | 13,16,19-Docosatrienoate | HMDB | 13,16,19-Docosatrienoic acid | HMDB | (13Z,16Z,19Z)-Docosatrienoate | HMDB | (13Z,16Z,19Z)-13,16,19-Docosatrienoic acid | HMDB | FA(22:3(13Z,16Z,19Z)) | HMDB | FA(22:3n3) | HMDB | cis-13,cis-16,cis-19-Docosatrienoic acid | HMDB | Docosatrienoic acid | HMDB |
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Chemical Formula | C22H38O2 |
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Average Molecular Weight | 334.5359 |
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Monoisotopic Molecular Weight | 334.28718046 |
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IUPAC Name | (13Z,16Z,19Z)-docosa-13,16,19-trienoic acid |
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Traditional Name | DTrE |
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CAS Registry Number | 28845-86-5 |
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SMILES | CC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C22H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10H,2,5,8,11-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9- |
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InChI Key | WBBQTNCISCKUMU-PDBXOOCHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 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 | Very long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Very 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 | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | 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 SectionsPredicted 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 - Docosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0007-4951000000-1aad4863d2ec911cb7a8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Docosatrienoic acid GC-MS (1 TMS) - 70eV, Positive | splash10-00ds-9883000000-0f3500426715a9c51ccf | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Docosatrienoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Docosatrienoic 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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 10V, Positive-QTOF | splash10-014r-0029000000-12563c9311c272b03ef4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 20V, Positive-QTOF | splash10-00n0-5493000000-291ecbb14a0d724890cd | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 40V, Positive-QTOF | splash10-06g3-9860000000-e96804bc997c3b08d694 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 10V, Negative-QTOF | splash10-001i-0019000000-12025f680802c5b83784 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 20V, Negative-QTOF | splash10-00m0-1039000000-e7477e45366329874498 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 40V, Negative-QTOF | splash10-052f-9130000000-a8051c16fa686909e011 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 10V, Negative-QTOF | splash10-001i-0009000000-31a1efc0c1d4ea277a4a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 20V, Negative-QTOF | splash10-00lr-1009000000-836d44588c0b993abebf | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 40V, Negative-QTOF | splash10-0006-9111000000-eb033fb8799e55aec4f9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 10V, Positive-QTOF | splash10-00kr-3339000000-ba30b08961f96e0795e3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 20V, Positive-QTOF | splash10-067i-9734000000-250c3c0d8fa667dd1b8c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Docosatrienoic acid 40V, Positive-QTOF | splash10-05po-9200000000-0b8ac85be8fec95c7ff1 | 2021-09-24 | Wishart Lab | View Spectrum |
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Disease References | Colorectal cancer |
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- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- 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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General References | - Soares MC, Alessio ML, Leger CL, Bluet-Pajot MT, Clauser H, Enjalbert A, Kordon C, Wandscheer DE: Effect of essential fatty acid deficiency on membrane fatty acid content and growth hormone stimulation of rat pituitaries during postnatal development. J Lipid Res. 1995 Jun;36(6):1401-6. [PubMed:7666016 ]
- Krutetskaia ZI, Lebedev OE, Roshchina NG, Butov SN: [The effect of docosatrienoic acid on the potassium channels of outward rectification in the membrane of rat peritoneal macrophages]. Fiziol Zh Im I M Sechenova. 1995 Jul;81(7):111-9. [PubMed:8714386 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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