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 03:04:07 UTC |
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Update Date | 2022-11-30 19:25:58 UTC |
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HMDB ID | HMDB0114908 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(18:1(11Z)/20:3(5Z,8Z,11Z)) |
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Description | PA(18:1(11Z)/20:3(5Z,8Z,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(18:1(11Z)/20:3(5Z,8Z,11Z)), in particular, consists of one chain of cis-vaccenic acid at the C-1 position and one chain of mead 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/CCCCCC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC InChI=1S/C41H73O8P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(43)49-39(38-48-50(44,45)46)37-47-40(42)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h14,16-17,19,22,24,28,30,39H,3-13,15,18,20-21,23,25-27,29,31-38H2,1-2H3,(H2,44,45,46)/b16-14-,19-17-,24-22-,30-28-/t39-/m1/s1 |
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Synonyms | Value | Source |
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1-cis-vaccenoyl-2-meadoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-cis-vaccenoyl-2-meadoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(18:1/20:3) | SMPDB, HMDB | PA(18:1n7/20:3n9) | SMPDB, HMDB | PA(18:1w7/20:3w9) | SMPDB, HMDB | PA(38:4) | SMPDB, HMDB | Phosphatidic acid(18:1(11Z)/20:3(5Z,8Z,11Z)) | SMPDB, HMDB | Phosphatidic acid(18:1/20:3) | SMPDB, HMDB | Phosphatidic acid(18:1n7/20:3n9) | SMPDB, HMDB | Phosphatidic acid(18:1w7/20:3w9) | SMPDB, HMDB | Phosphatidic acid(38:4) | SMPDB, HMDB | Phosphatidate(18:1(11Z)/20:3(5Z,8Z,11Z)) | SMPDB, HMDB | Phosphatidate(18:1/20:3) | SMPDB, HMDB | Phosphatidate(18:1n7/20:3n9) | SMPDB, HMDB | Phosphatidate(18:1w7/20:3w9) | SMPDB, HMDB | Phosphatidate(38:4) | SMPDB, HMDB | PA(18:1(11Z)/20:3(5Z,8Z,11Z)) | SMPDB | [(2R)-2-[(5Z,8Z,11Z)-Icosa-5,8,11-trienoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C41H73O8P |
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Average Molecular Weight | 725.001 |
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Monoisotopic Molecular Weight | 724.504306309 |
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IUPAC Name | [(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC |
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InChI Identifier | InChI=1S/C41H73O8P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(43)49-39(38-48-50(44,45)46)37-47-40(42)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h14,16-17,19,22,24,28,30,39H,3-13,15,18,20-21,23,25-27,29,31-38H2,1-2H3,(H2,44,45,46)/b16-14-,19-17-,24-22-,30-28-/t39-/m1/s1 |
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InChI Key | SWLSYTQCNTUXLR-ZQTJDSEGSA-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 | Not Available |
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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(18:1(11Z)/20:3(5Z,8Z,11Z)/18:1(11Z)) (PathBank: SMP0021867)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/18:1(9Z)) (PathBank: SMP0021868)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:1(11Z)) (PathBank: SMP0021869)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0021870)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:1(13Z)) (PathBank: SMP0021871)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/24:1(15Z)) (PathBank: SMP0021872)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)) (PathBank: SMP0021873)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0021874)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0021875)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z)) (PathBank: SMP0021876)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0021877)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0021878)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0021879)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0021880)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0021881)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0021882)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0021883)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0021884)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:2(11Z,14Z)) (PathBank: SMP0033087)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0033088)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:0) (PathBank: SMP0066273)
- De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/24:0) (PathBank: SMP0066280)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085217)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085218)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085219)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085220)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085221)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085222)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085223)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085224)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085225)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085226)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085227)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085228)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085229)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085230)
- Cardiolipin Biosynthesis CL(18:1(11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085231)
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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(18:1(11Z)/20:3(5Z,8Z,11Z)),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC | 5137.4 | Semi standard non polar | 33892256 | PA(18:1(11Z)/20:3(5Z,8Z,11Z)),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC | 4521.3 | Standard non polar | 33892256 | PA(18:1(11Z)/20:3(5Z,8Z,11Z)),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC | 5648.9 | Standard polar | 33892256 | PA(18:1(11Z)/20:3(5Z,8Z,11Z)),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC | 5107.9 | Semi standard non polar | 33892256 | PA(18:1(11Z)/20:3(5Z,8Z,11Z)),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC | 4485.0 | Standard non polar | 33892256 | PA(18:1(11Z)/20:3(5Z,8Z,11Z)),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC | 4913.1 | Standard polar | 33892256 | PA(18:1(11Z)/20:3(5Z,8Z,11Z)),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC | 5366.3 | Semi standard non polar | 33892256 | PA(18:1(11Z)/20:3(5Z,8Z,11Z)),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC | 4619.5 | Standard non polar | 33892256 | PA(18:1(11Z)/20:3(5Z,8Z,11Z)),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\CCCCCCCC | 5636.9 | 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(18:1(11Z)/20:3(5Z,8Z,11Z)) 10V, Positive-QTOF | splash10-0699-1192602400-a77b1e48dfebc3087757 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 20V, Positive-QTOF | splash10-00kk-2192212000-8f50c1f1d3962bba2fd1 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 40V, Positive-QTOF | splash10-007a-1095013000-7494404aba0fc0e80764 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 10V, Negative-QTOF | splash10-071i-4092300200-c555613d79ff7d58cbe9 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 20V, Negative-QTOF | splash10-004i-9050000000-3759dc98f9d59527f9c1 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 40V, Negative-QTOF | splash10-004i-9000000000-a3a2568d8051f6ff486e | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 10V, Negative-QTOF | splash10-00di-0000000900-503da6078c6f482f0a70 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 20V, Negative-QTOF | splash10-06l3-0033900400-aea534043355d742b7df | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 40V, Negative-QTOF | splash10-053r-1196600100-4c64ed3d5bc54ae8a3c7 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 10V, Positive-QTOF | splash10-0002-0000000900-c7217cc8b4fecc83cb81 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 20V, Positive-QTOF | splash10-0002-0000009900-9aeab714e87e1529316e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 40V, Positive-QTOF | splash10-00ke-0000902300-0c84845f6ef43415a187 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 10V, Positive-QTOF | splash10-0a6r-0000000900-f25618a4673f1c76e672 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 20V, Positive-QTOF | splash10-004i-0000005900-4871ac345f15ca0d32cd | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:1(11Z)/20:3(5Z,8Z,11Z)) 40V, Positive-QTOF | splash10-00ou-0000906200-20e6c1ec468f74264e6d | 2021-09-25 | Wishart Lab | View Spectrum |
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