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 04:58:37 UTC |
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Update Date | 2022-11-30 19:26:15 UTC |
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HMDB ID | HMDB0115539 |
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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)/18:1(9Z)) |
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Description | PA(20:2(11Z,14Z)/18:1(9Z)) 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)/18:1(9Z)), in particular, consists of one chain of eicosadienoic acid at the C-1 position and one chain of oleic 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)CCCCCCC\C=C/CCCCCCCC InChI=1S/C41H75O8P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h11,13,17-19,21,39H,3-10,12,14-16,20,22-38H2,1-2H3,(H2,44,45,46)/b13-11-,19-17-,21-18-/t39-/m1/s1 |
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Synonyms | Value | Source |
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1-eicosadienoyl-2-oleoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-eicosadienoyl-2-oleoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(20:2/18:1) | SMPDB, HMDB | PA(20:2n6/18:1n9) | SMPDB, HMDB | PA(20:2w6/18:1w9) | SMPDB, HMDB | PA(38:3) | SMPDB, HMDB | Phosphatidic acid(20:2(11Z,14Z)/18:1(9Z)) | SMPDB, HMDB | Phosphatidic acid(20:2/18:1) | SMPDB, HMDB | Phosphatidic acid(20:2n6/18:1n9) | SMPDB, HMDB | Phosphatidic acid(20:2w6/18:1w9) | SMPDB, HMDB | Phosphatidic acid(38:3) | SMPDB, HMDB | Phosphatidate(20:2(11Z,14Z)/18:1(9Z)) | SMPDB, HMDB | Phosphatidate(20:2/18:1) | SMPDB, HMDB | Phosphatidate(20:2n6/18:1n9) | SMPDB, HMDB | Phosphatidate(20:2w6/18:1w9) | SMPDB, HMDB | Phosphatidate(38:3) | SMPDB, HMDB | PA(20:2(11Z,14Z)/18:1(9Z)) | SMPDB |
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Chemical Formula | C41H75O8P |
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Average Molecular Weight | 727.017 |
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Monoisotopic Molecular Weight | 726.519956373 |
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IUPAC Name | [(2R)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-2-[(9Z)-octadec-9-enoyloxy]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)CCCCCCC\C=C/CCCCCCCC |
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InChI Identifier | InChI=1S/C41H75O8P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h11,13,17-19,21,39H,3-10,12,14-16,20,22-38H2,1-2H3,(H2,44,45,46)/b13-11-,19-17-,21-18-/t39-/m1/s1 |
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InChI Key | LRTCKJJOUNZFDD-DBHIXKHWSA-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)/18:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0034592)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0034593)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/18:1(9Z)/20:2(11Z,14Z)) (PathBank: SMP0034594)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/18:1(9Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0034595)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0034596)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0034597)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0034598)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/18:1(9Z)/22:2(13Z,16Z)) (PathBank: SMP0034599)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0034600)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0034601)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0034602)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0034603)
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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)/18:1(9Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 5146.6 | Semi standard non polar | 33892256 | PA(20:2(11Z,14Z)/18:1(9Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 4521.0 | Standard non polar | 33892256 | PA(20:2(11Z,14Z)/18:1(9Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC | 5757.9 | Standard polar | 33892256 | PA(20:2(11Z,14Z)/18:1(9Z)),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)CCCCCCC/C=C\CCCCCCCC | 5099.9 | Semi standard non polar | 33892256 | PA(20:2(11Z,14Z)/18:1(9Z)),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)CCCCCCC/C=C\CCCCCCCC | 4487.8 | Standard non polar | 33892256 | PA(20:2(11Z,14Z)/18:1(9Z)),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)CCCCCCC/C=C\CCCCCCCC | 4998.2 | Standard polar | 33892256 | PA(20:2(11Z,14Z)/18:1(9Z)),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)CCCCCCC/C=C\CCCCCCCC | 5378.2 | Semi standard non polar | 33892256 | PA(20:2(11Z,14Z)/18:1(9Z)),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)CCCCCCC/C=C\CCCCCCCC | 4612.1 | Standard non polar | 33892256 | PA(20:2(11Z,14Z)/18:1(9Z)),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)CCCCCCC/C=C\CCCCCCCC | 5739.4 | 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)/18:1(9Z)) 10V, Positive-QTOF | splash10-016v-1092502400-c421896ffab750f6c165 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 20V, Positive-QTOF | splash10-00kb-1192202000-338a00cf9546e770c068 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 40V, Positive-QTOF | splash10-00r2-1196013000-e4d7c15284e7fd5cded4 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 10V, Negative-QTOF | splash10-0570-5095400300-e3e4a24a2a55a446f424 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 20V, Negative-QTOF | splash10-004i-9032000000-9ac052f4f7dca7a4ed86 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 40V, Negative-QTOF | splash10-004i-9000000000-d09e7ddee8abc7c85f53 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 10V, Positive-QTOF | splash10-0a6r-0000000900-691560b7d6d5a73cf455 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 20V, Positive-QTOF | splash10-004i-0000005900-0420dac6d97cae3fc18b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 40V, Positive-QTOF | splash10-00os-0000906200-a2980fda22bd1cb30c68 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 10V, Positive-QTOF | splash10-0002-0000000900-7b0df16deb61c6842248 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 20V, Positive-QTOF | splash10-0udk-0000009900-c1f02a3b0e87ccabcf93 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 40V, Positive-QTOF | splash10-0ktn-0000902300-30e9291760424f47e633 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 10V, Negative-QTOF | splash10-004i-0000000900-880b430b6be90fb7c879 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 20V, Negative-QTOF | splash10-05ru-0033900400-1cb4919fed051a3922f9 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/18:1(9Z)) 40V, Negative-QTOF | splash10-0a59-1169600100-f4603c5f185f4fd976c8 | 2021-09-23 | Wishart Lab | View Spectrum |
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