Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-16 03:42:29 UTC |
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Update Date | 2022-03-07 03:17:52 UTC |
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HMDB ID | HMDB0062306 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate |
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Description | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate is classified as a member of the 1-acylglycerol-3-phosphates. 1-acylglycerol-3-phosphates are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position. 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate is considered to be practically insoluble (in water) and acidic. 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate is a glycerophosphate lipid molecule |
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Structure | [H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O InChI=1S/C25H47O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(27)31-22-24(26)23-32-33(28,29)30/h6-7,9-10,24,26H,2-5,8,11-23H2,1H3,(H2,28,29,30)/b7-6-,10-9-/t24-/m1/s1 |
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Synonyms | Value | Source |
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1-(13Z,16Z-Docosadienoyl)-glycero-3-phosphoric acid | Generator |
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Chemical Formula | C25H47O7P |
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Average Molecular Weight | 490.618 |
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Monoisotopic Molecular Weight | 490.305940851 |
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IUPAC Name | [(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-hydroxypropoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-hydroxypropoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O |
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InChI Identifier | InChI=1S/C25H47O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(27)31-22-24(26)23-32-33(28,29)30/h6-7,9-10,24,26H,2-5,8,11-23H2,1H3,(H2,28,29,30)/b7-6-,10-9-/t24-/m1/s1 |
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InChI Key | GFXKNONHFFXXOL-XBJNFHHOSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerophospholipids |
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Sub Class | Glycerophosphates |
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Direct Parent | 1-acylglycerol-3-phosphates |
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Alternative Parents | |
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Substituents | - 1-acylglycerol-3-phosphate
- Fatty acid ester
- Monoalkyl phosphate
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Alcohol
- Organooxygen compound
- 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 | Not Available |
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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 | Not Available |
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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 | 0.00067 g/l | ALOGPS | LogP | 6.20 | ALOGPS |
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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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1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C | 3682.0 | Semi standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,1TMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C | 3663.1 | Semi standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C | 3658.1 | Semi standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C | 3375.2 | Standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C | 4230.0 | Standard polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3651.7 | Semi standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3392.7 | Standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3954.2 | Standard polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,3TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3644.2 | Semi standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,3TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3391.6 | Standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,3TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3672.9 | Standard polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C | 3925.6 | Semi standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,1TBDMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 3879.8 | Semi standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4113.9 | Semi standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3658.7 | Standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4243.2 | Standard polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TBDMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4089.3 | Semi standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TBDMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3643.6 | Standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,2TBDMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4052.2 | Standard polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,3TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4311.3 | Semi standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,3TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3750.8 | Standard non polar | 33892256 | 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate,3TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3812.0 | Standard polar | 33892256 |
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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 - 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate GC-MS (1 TMS) - 70eV, Positive | splash10-01ot-9431000000-74903ff7272ce5ffb65a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate 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 - 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate 10V, Negative-QTOF | splash10-000i-0000900000-8f77a88ae04740383aef | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate 20V, Negative-QTOF | splash10-000i-0000900000-8f77a88ae04740383aef | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate 40V, Negative-QTOF | splash10-0f79-2905600000-275eefa6865b59d47913 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate 10V, Positive-QTOF | splash10-0006-0000900000-99882c53809428d07aff | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate 20V, Positive-QTOF | splash10-0006-0000900000-99882c53809428d07aff | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 1-(13Z,16Z-docosadienoyl)-glycero-3-phosphate 40V, Positive-QTOF | splash10-00di-0905700000-c6193c22e6a3e320a891 | 2021-09-22 | Wishart Lab | View Spectrum |
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General References | - Moritz A, De Graan PN, Gispen WH, Wirtz KW: Phosphatidic acid is a specific activator of phosphatidylinositol-4-phosphate kinase. J Biol Chem. 1992 Apr 15;267(11):7207-10. [PubMed:1313792 ]
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- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- Moolenaar WH, Kruijer W, Tilly BC, Verlaan I, Bierman AJ, de Laat SW: Growth factor-like action of phosphatidic acid. Nature. 1986 Sep 11-17;323(6084):171-3. [PubMed:3748188 ]
- Yang CY, Frohman MA: Mitochondria: signaling with phosphatidic acid. Int J Biochem Cell Biol. 2012 Aug;44(8):1346-50. doi: 10.1016/j.biocel.2012.05.006. Epub 2012 May 15. [PubMed:22609101 ]
- Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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