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 03:17:11 UTC |
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Update Date | 2022-11-30 19:26:00 UTC |
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HMDB ID | HMDB0114990 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) |
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Description | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 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(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one chain of gamma-linolenic acid at the C-1 position and one chain of eicosapentaenoic 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)CCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C41H65O8P/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/h5,7,11-14,17-19,21-22,24-25,27-28,30,39H,3-4,6,8-10,15-16,20,23,26,29,31-38H2,1-2H3,(H2,44,45,46)/b7-5-,13-11-,14-12-,19-17-,21-18-,24-22-,27-25-,30-28-/t39-/m1/s1 |
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Synonyms | Value | Source |
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1-gamma-Linolenoyl-2-eicosapentaenoyl-sn-glycero-3-phosphate | HMDB | 1-gamma-Linolenoyl-2-eicosapentaenoyl-sn-phosphatidic acid | HMDB | PA(18:3/20:5) | HMDB | PA(18:3N6/20:5N3) | HMDB | PA(18:3W6/20:5W3) | HMDB | PA(38:8) | HMDB | Phosphatidic acid(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | HMDB | Phosphatidic acid(18:3/20:5) | HMDB | Phosphatidic acid(18:3n6/20:5n3) | HMDB | Phosphatidic acid(18:3W6/20:5W3) | HMDB | Phosphatidic acid(38:8) | HMDB | Phosphatidate(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | HMDB | Phosphatidate(18:3/20:5) | HMDB | Phosphatidate(18:3N6/20:5N3) | HMDB | Phosphatidate(18:3W6/20:5W3) | HMDB | Phosphatidate(38:8) | HMDB | 1-gamma-linolenoyl-2-eicosapentaenoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-gamma-linolenoyl-2-eicosapentaenoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(18:3/20:5) | SMPDB, HMDB | PA(18:3n6/20:5n3) | SMPDB, HMDB | PA(18:3w6/20:5w3) | SMPDB, HMDB | PA(38:8) | SMPDB, HMDB | Phosphatidic acid(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | SMPDB, HMDB | Phosphatidic acid(18:3/20:5) | SMPDB, HMDB | Phosphatidic acid(18:3n6/20:5n3) | SMPDB, HMDB | Phosphatidic acid(18:3w6/20:5w3) | SMPDB, HMDB | Phosphatidic acid(38:8) | SMPDB, HMDB | Phosphatidate(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | SMPDB, HMDB | Phosphatidate(18:3/20:5) | SMPDB, HMDB | Phosphatidate(18:3n6/20:5n3) | SMPDB, HMDB | Phosphatidate(18:3w6/20:5w3) | SMPDB, HMDB | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | SMPDB |
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Chemical Formula | C41H65O8P |
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Average Molecular Weight | 716.937 |
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Monoisotopic Molecular Weight | 716.441706051 |
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IUPAC Name | [(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C41H65O8P/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/h5,7,11-14,17-19,21-22,24-25,27-28,30,39H,3-4,6,8-10,15-16,20,23,26,29,31-38H2,1-2H3,(H2,44,45,46)/b7-5-,13-11-,14-12-,19-17-,21-18-,24-22-,27-25-,30-28-/t39-/m1/s1 |
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InChI Key | ZIPIEDLWDARWQD-NXZDYZCBSA-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- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0075766)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0075770)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0075773)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0091044)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0091045)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)) (PathBank: SMP0075775)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)) (PathBank: SMP0067019)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)) (PathBank: SMP0075768)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0) (PathBank: SMP0075774)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0) (PathBank: SMP0091040)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0024688)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0024689)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0024693)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0024694)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0024695)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:2(11Z,14Z)) (PathBank: SMP0033359)
- De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0033360)
- Cardiolipin Biosynthesis CL(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0086510)
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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 IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | [H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5633.8 | Standard polar | 33892256 | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | [H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 4419.7 | Standard non polar | 33892256 | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | [H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5134.5 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCC/C=C\C/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C | 5174.0 | Semi standard non polar | 33892256 | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCC/C=C\C/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C | 4562.5 | Standard non polar | 33892256 | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCC/C=C\C/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C | 4993.5 | Standard polar | 33892256 | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCC/C=C\C/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 5121.5 | Semi standard non polar | 33892256 | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCC/C=C\C/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4529.7 | Standard non polar | 33892256 | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCC/C=C\C/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4409.2 | Standard polar | 33892256 | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCC/C=C\C/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5388.3 | Semi standard non polar | 33892256 | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCC/C=C\C/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4688.9 | Standard non polar | 33892256 | PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCC/C=C\C/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5026.7 | 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(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Positive-QTOF | splash10-014r-1192604300-a24ec8aea095a37f1a43 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Positive-QTOF | splash10-029j-2192212000-bc1ea56e6d8f9deb8f67 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Positive-QTOF | splash10-00kr-1094012000-3e2ddb048cf48783829a | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Negative-QTOF | splash10-056r-4092300200-979019a6a90f2e6068dc | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Negative-QTOF | splash10-004i-9050000000-c6b77069c920f48f460d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Negative-QTOF | splash10-004i-9000000000-5f2255cf9feeec4129d6 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Negative-QTOF | splash10-014i-0000000900-a17617836514233694c7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Negative-QTOF | splash10-0jr9-0033900400-2514115b3e115ec258e9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Negative-QTOF | splash10-0fb9-1196600100-285ba3be303793200c01 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Positive-QTOF | splash10-00kb-0000009500-8e305592ff99e63ed645 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Positive-QTOF | splash10-014i-0000007900-397959807ad87acbcac9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Positive-QTOF | splash10-014i-0000907100-24602a7bce599d161c08 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Positive-QTOF | splash10-000i-0000000900-22f648ca106818f18ab4 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Positive-QTOF | splash10-000o-0000009900-3fd62b528331a36cf7d6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Positive-QTOF | splash10-000i-0000902300-8c09ef045e70e44ad3b6 | 2021-09-24 | 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 | 74876736 |
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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 | 52928981 |
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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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