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 02:41:42 UTC |
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Update Date | 2022-11-30 19:25:54 UTC |
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HMDB ID | HMDB0114782 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(14:0/18:4(6Z,9Z,12Z,15Z)) |
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Description | PA(14:0/18:4(6Z,9Z,12Z,15Z)) 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(14:0/18:4(6Z,9Z,12Z,15Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of stearidonic 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)CCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C35H61O8P/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-35(37)43-33(32-42-44(38,39)40)31-41-34(36)29-27-25-23-21-19-14-12-10-8-6-4-2/h5,7,11,13,16-17,20,22,33H,3-4,6,8-10,12,14-15,18-19,21,23-32H2,1-2H3,(H2,38,39,40)/b7-5-,13-11-,17-16-,22-20-/t33-/m1/s1 |
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Synonyms | Value | Source |
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1-Myristoyl-2-stearidonoyl-sn-glycero-3-phosphate | HMDB | 1-Myristoyl-2-stearidonoyl-sn-phosphatidic acid | HMDB | PA(14:0/18:4) | HMDB | PA(14:0/18:4N3) | HMDB | PA(14:0/18:4W3) | HMDB | PA(32:4) | HMDB | Phosphatidic acid(14:0/18:4(6Z,9Z,12Z,15Z)) | HMDB | Phosphatidic acid(14:0/18:4) | HMDB | Phosphatidic acid(14:0/18:4n3) | HMDB | Phosphatidic acid(14:0/18:4W3) | HMDB | Phosphatidic acid(32:4) | HMDB | Phosphatidate(14:0/18:4(6Z,9Z,12Z,15Z)) | HMDB | Phosphatidate(14:0/18:4) | HMDB | Phosphatidate(14:0/18:4N3) | HMDB | Phosphatidate(14:0/18:4W3) | HMDB | Phosphatidate(32:4) | HMDB | 1-myristoyl-2-stearidonoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-myristoyl-2-stearidonoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(14:0/18:4) | SMPDB, HMDB | PA(14:0/18:4n3) | SMPDB, HMDB | PA(14:0/18:4w3) | SMPDB, HMDB | PA(32:4) | SMPDB, HMDB | Phosphatidic acid(14:0/18:4(6Z,9Z,12Z,15Z)) | SMPDB, HMDB | Phosphatidic acid(14:0/18:4) | SMPDB, HMDB | Phosphatidic acid(14:0/18:4n3) | SMPDB, HMDB | Phosphatidic acid(14:0/18:4w3) | SMPDB, HMDB | Phosphatidic acid(32:4) | SMPDB, HMDB | Phosphatidate(14:0/18:4(6Z,9Z,12Z,15Z)) | SMPDB, HMDB | Phosphatidate(14:0/18:4) | SMPDB, HMDB | Phosphatidate(14:0/18:4n3) | SMPDB, HMDB | Phosphatidate(14:0/18:4w3) | SMPDB, HMDB | PA(14:0/18:4(6Z,9Z,12Z,15Z)) | SMPDB |
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Chemical Formula | C35H61O8P |
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Average Molecular Weight | 640.839 |
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Monoisotopic Molecular Weight | 640.410405922 |
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IUPAC Name | [(2R)-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]-3-(tetradecanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]-3-(tetradecanoyloxy)propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C35H61O8P/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-35(37)43-33(32-42-44(38,39)40)31-41-34(36)29-27-25-23-21-19-14-12-10-8-6-4-2/h5,7,11,13,16-17,20,22,33H,3-4,6,8-10,12,14-15,18-19,21,23-32H2,1-2H3,(H2,38,39,40)/b7-5-,13-11-,17-16-,22-20-/t33-/m1/s1 |
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InChI Key | CNTQTQQWDNRDJY-GSBCBEKWSA-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(14:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0064165)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0064170)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)) (PathBank: SMP0064176)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:0) (PathBank: SMP0072917)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z)) (PathBank: SMP0072918)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0072930)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0072931)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0088185)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z)) (PathBank: SMP0088189)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0088192)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z)) (PathBank: SMP0088196)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:0) (PathBank: SMP0064174)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:0) (PathBank: SMP0064181)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) (PathBank: SMP0072919)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0088186)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0088187)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0088191)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0072920)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/14:0) (PathBank: SMP0016788)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/15:0) (PathBank: SMP0016789)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/16:0) (PathBank: SMP0016790)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/18:0) (PathBank: SMP0016791)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/14:1(9Z)) (PathBank: SMP0016795)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/16:1(9Z)) (PathBank: SMP0016796)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/18:1(11Z)) (PathBank: SMP0016797)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/18:1(9Z)) (PathBank: SMP0016798)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/18:2(9Z,12Z)) (PathBank: SMP0016803)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0016804)
- De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0016809)
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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(14:0/18:4(6Z,9Z,12Z,15Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4545.1 | Semi standard non polar | 33892256 | PA(14:0/18:4(6Z,9Z,12Z,15Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4055.7 | Standard non polar | 33892256 | PA(14:0/18:4(6Z,9Z,12Z,15Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5297.3 | Standard polar | 33892256 | PA(14:0/18:4(6Z,9Z,12Z,15Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4510.6 | Semi standard non polar | 33892256 | PA(14:0/18:4(6Z,9Z,12Z,15Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4036.3 | Standard non polar | 33892256 | PA(14:0/18:4(6Z,9Z,12Z,15Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4586.8 | Standard polar | 33892256 | PA(14:0/18:4(6Z,9Z,12Z,15Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4758.8 | Semi standard non polar | 33892256 | PA(14:0/18:4(6Z,9Z,12Z,15Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4174.8 | Standard non polar | 33892256 | PA(14:0/18:4(6Z,9Z,12Z,15Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5287.6 | Standard polar | 33892256 | PA(14:0/18:4(6Z,9Z,12Z,15Z)),2TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4955.9 | Semi standard non polar | 33892256 | PA(14:0/18:4(6Z,9Z,12Z,15Z)),2TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4223.3 | Standard non polar | 33892256 | PA(14:0/18:4(6Z,9Z,12Z,15Z)),2TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4646.2 | 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(14:0/18:4(6Z,9Z,12Z,15Z)) 10V, Positive-QTOF | splash10-06r6-1193114000-22e61fae47eee8bb2bfb | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 20V, Positive-QTOF | splash10-07wa-2392110000-604f384018125658257b | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 40V, Positive-QTOF | splash10-015i-1391020000-3b2af9826353156711df | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 10V, Negative-QTOF | splash10-004i-3092002000-98411999fdfdc6944375 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 20V, Negative-QTOF | splash10-004i-9050000000-86aee7108243a407a296 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 40V, Negative-QTOF | splash10-004i-9000000000-3d8199e51c39b8e9381a | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 10V, Positive-QTOF | splash10-00dl-0000009000-08947541ff96d7691f9c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 20V, Positive-QTOF | splash10-0006-0000059000-abaeb11196718037f582 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 40V, Positive-QTOF | splash10-0296-0006693000-bda77b46516989f331fd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 10V, Positive-QTOF | splash10-03di-0000009000-43696592d61cf3abe148 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 20V, Positive-QTOF | splash10-04i0-0000099000-06867d29a943192b15d1 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 40V, Positive-QTOF | splash10-01p9-0003934000-37349f83c27a16b302ef | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 10V, Negative-QTOF | splash10-000i-0000009000-becfb690d3729d25614c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 20V, Negative-QTOF | splash10-01ti-1197506000-3b380a55876178de8d02 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(14:0/18:4(6Z,9Z,12Z,15Z)) 40V, Negative-QTOF | splash10-004i-0091100000-0d4ab674493d042e8f88 | 2021-09-23 | 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 | 74876549 |
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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 | 52929516 |
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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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