Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-09-09 04:59:22 UTC |
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Update Date | 2022-11-30 19:26:15 UTC |
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HMDB ID | HMDB0115544 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(20:2(11Z,14Z)/20:1(11Z)) |
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Description | PA(20:2(11Z,14Z)/20:1(11Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(20:2(11Z,14Z)/20:1(11Z)), in particular, consists of one chain of eicosadienoic acid at the C-1 position and one chain of eicosenoic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. |
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Structure | [H][C@@](COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/CCCCCCCC InChI=1S/C43H79O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-42(44)49-39-41(40-50-52(46,47)48)51-43(45)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11,13,17-20,41H,3-10,12,14-16,21-40H2,1-2H3,(H2,46,47,48)/b13-11-,19-17-,20-18-/t41-/m1/s1 |
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Synonyms | Value | Source |
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1-eicosadienoyl-2-eicosenoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-eicosadienoyl-2-eicosenoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(20:2/20:1) | SMPDB, HMDB | PA(20:2n6/20:1n9) | SMPDB, HMDB | PA(20:2w6/20:1w9) | SMPDB, HMDB | PA(40:3) | SMPDB, HMDB | Phosphatidic acid(20:2(11Z,14Z)/20:1(11Z)) | SMPDB, HMDB | Phosphatidic acid(20:2/20:1) | SMPDB, HMDB | Phosphatidic acid(20:2n6/20:1n9) | SMPDB, HMDB | Phosphatidic acid(20:2w6/20:1w9) | SMPDB, HMDB | Phosphatidic acid(40:3) | SMPDB, HMDB | Phosphatidate(20:2(11Z,14Z)/20:1(11Z)) | SMPDB, HMDB | Phosphatidate(20:2/20:1) | SMPDB, HMDB | Phosphatidate(20:2n6/20:1n9) | SMPDB, HMDB | Phosphatidate(20:2w6/20:1w9) | SMPDB, HMDB | Phosphatidate(40:3) | SMPDB, HMDB | PA(20:2(11Z,14Z)/20:1(11Z)) | SMPDB |
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Chemical Formula | C43H79O8P |
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Average Molecular Weight | 755.071 |
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Monoisotopic Molecular Weight | 754.551256502 |
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IUPAC Name | [(2R)-2-[(11Z)-icos-11-enoyloxy]-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-2-[(11Z)-icos-11-enoyloxy]-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/CCCCCCCC |
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InChI Identifier | InChI=1S/C43H79O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-42(44)49-39-41(40-50-52(46,47)48)51-43(45)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11,13,17-20,41H,3-10,12,14-16,21-40H2,1-2H3,(H2,46,47,48)/b13-11-,19-17-,20-18-/t41-/m1/s1 |
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InChI Key | RTVYRNMZZMMGAN-LGYIKAGVSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages. |
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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 | 1,2-diacylglycerol-3-phosphates |
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Alternative Parents | |
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Substituents | - 1,2-diacylglycerol-3-phosphate
- Fatty acid ester
- Monoalkyl phosphate
- Dicarboxylic acid or derivatives
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Carboxylic acid ester
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- 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 | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0034664)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0034665)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/20:2(11Z,14Z)) (PathBank: SMP0034666)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0034667)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0034668)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0034669)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0034670)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/22:2(13Z,16Z)) (PathBank: SMP0034671)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0034672)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0034673)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0034674)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0034675)
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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PA(20:2(11Z,14Z)/20:1(11Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\CCCCCCCC | 5362.5 | Semi standard non polar | 33892256 | PA(20:2(11Z,14Z)/20:1(11Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\CCCCCCCC | 4685.4 | Standard non polar | 33892256 | PA(20:2(11Z,14Z)/20:1(11Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\CCCCCCCC | 5929.7 | Standard polar | 33892256 | PA(20:2(11Z,14Z)/20:1(11Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\CCCCCCCC | 5306.5 | Semi standard non polar | 33892256 | PA(20:2(11Z,14Z)/20:1(11Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\CCCCCCCC | 4651.9 | Standard non polar | 33892256 | PA(20:2(11Z,14Z)/20:1(11Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\CCCCCCCC | 5168.4 | Standard polar | 33892256 | PA(20:2(11Z,14Z)/20:1(11Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC/C=C\CCCCCCCC | 5592.3 | Semi standard non polar | 33892256 | PA(20:2(11Z,14Z)/20:1(11Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC/C=C\CCCCCCCC | 4771.4 | Standard non polar | 33892256 | PA(20:2(11Z,14Z)/20:1(11Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC/C=C\CCCCCCCC | 5907.9 | Standard polar | 33892256 |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 10V, Positive-QTOF | splash10-052e-1164903600-bc0ac86b45b22222516f | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 20V, Positive-QTOF | splash10-0002-3295504200-52da4fade84035f6741c | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 40V, Positive-QTOF | splash10-00ke-1189104000-e74afb3266176cbae0d9 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 10V, Negative-QTOF | splash10-0pdr-8089800600-777686455df52e00713b | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 20V, Negative-QTOF | splash10-004i-9022000000-c6f706dd899132daf965 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 40V, Negative-QTOF | splash10-004i-9000000000-5f6b78559f2487786432 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 10V, Positive-QTOF | splash10-004i-0000000900-44de4af0a2c45d16b2de | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 20V, Positive-QTOF | splash10-004i-0000009900-f1904a07d550fbfdd6c2 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 40V, Positive-QTOF | splash10-0170-0000902300-8e157c98f06c47d54436 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 10V, Positive-QTOF | splash10-052r-0000000900-b900051551a00a8f477d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 20V, Positive-QTOF | splash10-0a4i-0000005900-0b5db6b792e21b8dd097 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 40V, Positive-QTOF | splash10-052b-0000906200-e8e7601b65bbc14a3ca9 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 10V, Negative-QTOF | splash10-0udi-0000000900-20a88bbe2594111b579b | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 20V, Negative-QTOF | splash10-0pbd-0006900400-1439155df05522b7aa65 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/20:1(11Z)) 40V, Negative-QTOF | splash10-0a4i-0009300000-8a72fad03d3b9e0aae0b | 2021-09-25 | Wishart Lab | View Spectrum |
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