Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-09-12 01:27:20 UTC |
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Update Date | 2022-03-07 02:49:56 UTC |
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HMDB ID | HMDB0007861 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PA(18:0/18:2(9Z,12Z)) |
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Description | PA(18:0/18:2(9Z,12Z)) 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(18:0/18:2(9Z,12Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the linoleic acid moiety is derived from seed oils. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-CoA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218 , 16185776 ). |
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Structure | CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C39H73O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,37H,3-11,13,15-17,19,21-36H2,1-2H3,(H2,42,43,44)/b14-12-,20-18-/t37-/m1/s1 |
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Synonyms | Value | Source |
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(2R)-1-(Phosphonooxy)-3-(stearoyloxy)propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate | ChEBI | 1-18:0-2-18:2-Phosphatidic acid | ChEBI | 1-Octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate | ChEBI | 1-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphate | ChEBI | 18:0-18:2-PA | ChEBI | PA(18:0/18:2) | ChEBI | PA(18:0/18:2N6) | ChEBI | PA(18:0/18:2OMEGA6) | ChEBI | PA(36:2) | ChEBI | Phosphatidic acid(18:0/18:2) | ChEBI | Phosphatidic acid(18:0/18:2n6) | ChEBI | Phosphatidic acid(18:0/18:2omega6) | ChEBI | Phosphatidic acid(36:2) | ChEBI | (2R)-1-(Phosphonooxy)-3-(stearoyloxy)propan-2-yl (9Z,12Z)-octadeca-9,12-dienoic acid | Generator | 1-18:0-2-18:2-Phosphatidate | Generator | 1-Octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoric acid | Generator | 1-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoric acid | Generator | Phosphatidate(18:0/18:2) | Generator | Phosphatidate(18:0/18:2N6) | Generator | Phosphatidate(18:0/18:2OMEGA6) | Generator | Phosphatidate(36:2) | Generator | 1-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-phosphatidic acid | HMDB | 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphate | HMDB | PA(18:0/18:2W6) | HMDB | Phosphatidic acid(18:0/18:2W6) | HMDB |
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Chemical Formula | C39H73O8P |
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Average Molecular Weight | 700.9659 |
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Monoisotopic Molecular Weight | 700.504305824 |
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IUPAC Name | [(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C39H73O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,37H,3-11,13,15-17,19,21-36H2,1-2H3,(H2,42,43,44)/b14-12-,20-18-/t37-/m1/s1 |
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InChI Key | QYYWMYCDFOLKKH-DAKWMOBOSA-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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Not Available | 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(18:0/18:2(9Z,12Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4930.3 | Semi standard non polar | 33892256 | PA(18:0/18:2(9Z,12Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4397.9 | Standard non polar | 33892256 | PA(18:0/18:2(9Z,12Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5767.6 | Standard polar | 33892256 | PA(18:0/18:2(9Z,12Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4903.2 | Semi standard non polar | 33892256 | PA(18:0/18:2(9Z,12Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4371.8 | Standard non polar | 33892256 | PA(18:0/18:2(9Z,12Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 5048.0 | Standard polar | 33892256 | PA(18:0/18:2(9Z,12Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5165.2 | Semi standard non polar | 33892256 | PA(18:0/18:2(9Z,12Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4490.3 | Standard non polar | 33892256 | PA(18:0/18:2(9Z,12Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5753.6 | 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 - PA(18:0/18:2(9Z,12Z)) GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2022-08-08 | 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 - PA(18:0/18:2(9Z,12Z)) 10V, Positive-QTOF | splash10-0uxr-1171905400-69c1fb870dc2dc7f674d | 2015-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 20V, Positive-QTOF | splash10-014j-2393505000-7d80d3958dc3cc4c8a77 | 2015-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 40V, Positive-QTOF | splash10-00vl-0194233000-72a24588ee17dea63d32 | 2015-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 10V, Negative-QTOF | splash10-017j-4090403000-d4941212f149135595b6 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 20V, Negative-QTOF | splash10-004i-9050000000-9db11b1be5dca535d31c | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 40V, Negative-QTOF | splash10-004i-9000000000-1272fe43292da7553178 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 10V, Positive-QTOF | splash10-00di-0000000900-af2da6ae565960d02a74 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 20V, Positive-QTOF | splash10-00i0-0000009900-7e41e59856bf50ddbb3c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 40V, Positive-QTOF | splash10-0773-0000902300-bc749dd94af6446df65a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 10V, Negative-QTOF | splash10-0002-0000009000-55a7c1167cbe0f25b0be | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 20V, Negative-QTOF | splash10-017j-0060904000-916fe5b246329a558e98 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 40V, Negative-QTOF | splash10-003r-0090300000-8b54e6cad8c14493034c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 10V, Positive-QTOF | splash10-0f89-0000009500-c84c90ec7d2e858c69f3 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 20V, Positive-QTOF | splash10-0udi-0000007900-6386210cf4e9425daf33 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:0/18:2(9Z,12Z)) 40V, Positive-QTOF | splash10-0v4i-0000907100-042e00adfff6b52cf41c | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum |
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