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 03:44:39 UTC |
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Update Date | 2022-11-30 19:26:04 UTC |
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HMDB ID | HMDB0115148 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) |
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Description | PA(20:4(5Z,8Z,11Z,14Z)/16:1(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(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)), in particular, consists of one chain of arachidonic acid at the C-1 position and one chain of palmitoleic 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)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCC InChI=1S/C39H67O8P/c1-3-5-7-9-11-13-15-17-18-19-20-22-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-21-16-14-12-10-8-6-4-2/h11,13-14,16-18,20,22,25,27,37H,3-10,12,15,19,21,23-24,26,28-36H2,1-2H3,(H2,42,43,44)/b13-11-,16-14-,18-17-,22-20-,27-25-/t37-/m1/s1 |
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Synonyms | Value | Source |
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1-Arachidonoyl-2-palmitoleoyl-sn-glycero-3-phosphate | HMDB | 1-Arachidonoyl-2-palmitoleoyl-sn-phosphatidic acid | HMDB | PA(20:4/16:1) | HMDB | PA(20:4N6/16:1N7) | HMDB | PA(20:4W6/16:1W7) | HMDB | PA(36:5) | HMDB | Phosphatidic acid(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) | HMDB | Phosphatidic acid(20:4/16:1) | HMDB | Phosphatidic acid(20:4n6/16:1n7) | HMDB | Phosphatidic acid(20:4W6/16:1W7) | HMDB | Phosphatidic acid(36:5) | HMDB | Phosphatidate(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) | HMDB | Phosphatidate(20:4/16:1) | HMDB | Phosphatidate(20:4N6/16:1N7) | HMDB | Phosphatidate(20:4W6/16:1W7) | HMDB | Phosphatidate(36:5) | HMDB | 1-arachidonoyl-2-palmitoleoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-arachidonoyl-2-palmitoleoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(20:4/16:1) | SMPDB, HMDB | PA(20:4n6/16:1n7) | SMPDB, HMDB | PA(20:4w6/16:1w7) | SMPDB, HMDB | PA(36:5) | SMPDB, HMDB | Phosphatidic acid(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) | SMPDB, HMDB | Phosphatidic acid(20:4/16:1) | SMPDB, HMDB | Phosphatidic acid(20:4n6/16:1n7) | SMPDB, HMDB | Phosphatidic acid(20:4w6/16:1w7) | SMPDB, HMDB | Phosphatidic acid(36:5) | SMPDB, HMDB | Phosphatidate(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) | SMPDB, HMDB | Phosphatidate(20:4/16:1) | SMPDB, HMDB | Phosphatidate(20:4n6/16:1n7) | SMPDB, HMDB | Phosphatidate(20:4w6/16:1w7) | SMPDB, HMDB | PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) | SMPDB |
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Chemical Formula | C39H67O8P |
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Average Molecular Weight | 694.931 |
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Monoisotopic Molecular Weight | 694.457356115 |
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IUPAC Name | [(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCC |
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InChI Identifier | InChI=1S/C39H67O8P/c1-3-5-7-9-11-13-15-17-18-19-20-22-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-21-16-14-12-10-8-6-4-2/h11,13-14,16-18,20,22,25,27,37H,3-10,12,15,19,21,23-24,26,28-36H2,1-2H3,(H2,42,43,44)/b13-11-,16-14-,18-17-,22-20-,27-25-/t37-/m1/s1 |
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InChI Key | TZUXUCWGFBDAOF-XMQUFBQNSA-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 | |
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Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) (PathBank: SMP0072010)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0072014)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)) (PathBank: SMP0072018)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0072029)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0079811)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0095073)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0095077)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)) (PathBank: SMP0072011)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) (PathBank: SMP0072012)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) (PathBank: SMP0072013)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0072016)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0072022)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0072024)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0072028)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0095081)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0095083)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0072021)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0072017)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0072020)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0024797)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:2(13Z,16Z)) (PathBank: SMP0024798)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0024799)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0024800)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0024801)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0024802)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0024803)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0024804)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0024805)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0024806)
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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 | | Show more...
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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(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCC | 4930.0 | Semi standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCC | 4362.3 | Standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCC | 5342.3 | Standard polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCC | 4910.7 | Semi standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCC | 4329.9 | Standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCC | 4631.5 | Standard polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCC | 5147.2 | Semi standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCC | 4476.3 | Standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCC | 5338.3 | Standard polar | 33892256 |
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Spectra |
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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(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 10V, Positive-QTOF | splash10-000m-1193315000-0cab2f024f90f731b6ab | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 20V, Positive-QTOF | splash10-000b-2292121000-264bdea0e82e2cb537b2 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 40V, Positive-QTOF | splash10-052k-1395022000-60f4061b4af92ee09111 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 10V, Negative-QTOF | splash10-0udr-5095303000-d919df3c588ded8bcc4d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 20V, Negative-QTOF | splash10-004i-9033000000-e3131070f184a50f00d7 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 40V, Negative-QTOF | splash10-004i-9000000000-32af693834db117f9c16 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 10V, Negative-QTOF | splash10-0006-0000009000-4f67b6407c110ededfb0 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 20V, Negative-QTOF | splash10-0f7c-1149906000-eafa0d55ae08314f82c9 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 40V, Negative-QTOF | splash10-0udi-1159301000-0d914a7541399d4da257 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 10V, Positive-QTOF | splash10-014i-0000000900-e6be93f355860a27326b | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 20V, Positive-QTOF | splash10-014i-0000009900-9f3691a8c67c438d4409 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 40V, Positive-QTOF | splash10-03yi-0000902300-12cefbc0118b18d1d004 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 10V, Positive-QTOF | splash10-004j-0000009000-7e7fd23bd5202e8e1a80 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 20V, Positive-QTOF | splash10-0002-0000059000-bfb4b27e1dbd2022c895 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) 40V, Positive-QTOF | splash10-0007-0006693000-a87fd8c71c05bd62f701 | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 74876890 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 52929217 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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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 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- 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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