Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-09-25 13:35:12 UTC |
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Update Date | 2022-03-07 02:51:01 UTC |
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HMDB ID | HMDB0010655 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) |
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Description | PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols 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. PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the arachidonic acid moiety is derived from animal fats and eggs. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. |
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Structure | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C44H75O10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-44(48)54-42(40-53-55(49,50)52-38-41(46)37-45)39-51-43(47)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-22,24,28,30,41-42,45-46H,3-10,15-16,20,23,25-27,29,31-40H2,1-2H3,(H,49,50)/b13-11-,14-12-,19-17-,21-18-,24-22-,30-28-/t41-,42+/m0/s1 |
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Synonyms | Value | Source |
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1-(9Z,12Z-Octadecadienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1'-glycerol) | HMDB | 1-Linoleoyl-2-arachidonoyl-sn-glycero-3-phosphoglycerol | HMDB | GPG(18:2/20:4) | HMDB | GPG(18:2N6/20:4N6) | HMDB | GPG(18:2W6/20:4W6) | HMDB | GPG(38:6) | HMDB | PG(18:2/20:4) | HMDB | PG(18:2N6/20:4N6) | HMDB | PG(18:2W6/20:4W6) | HMDB | PG(38:6) | HMDB | Phosphatidylglycerol(18:2/20:4) | HMDB | Phosphatidylglycerol(18:2n6/20:4n6) | HMDB | Phosphatidylglycerol(18:2W6/20:4W6) | HMDB | Phosphatidylglycerol(38:6) | HMDB | 1-(9Z,12Z-Octadecadienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoglycerol | HMDB | PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) | Lipid Annotator |
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Chemical Formula | C44H75O10P |
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Average Molecular Weight | 795.0341 |
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Monoisotopic Molecular Weight | 794.509785132 |
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IUPAC Name | [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid |
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Traditional Name | (2S)-2,3-dihydroxypropoxy(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C44H75O10P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-44(48)54-42(40-53-55(49,50)52-38-41(46)37-45)39-51-43(47)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-22,24,28,30,41-42,45-46H,3-10,15-16,20,23,25-27,29,31-40H2,1-2H3,(H,49,50)/b13-11-,14-12-,19-17-,21-18-,24-22-,30-28-/t41-,42+/m0/s1 |
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InChI Key | MMWTVDJVEFZVRA-KJNUSYEHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. |
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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 | Glycerophosphoglycerols |
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Direct Parent | Phosphatidylglycerols |
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Alternative Parents | |
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Substituents | - 1,2-diacylglycerophosphoglycerol
- Fatty acid ester
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- 1,2-diol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Organic oxide
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Primary alcohol
- Carbonyl group
- Hydrocarbon derivative
- 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(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0071865)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0071867)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0) (PathBank: SMP0071869)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)) (PathBank: SMP0071872)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0071875)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0071876)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0071883)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0071888)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0079653)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0) (PathBank: SMP0079656)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)) (PathBank: SMP0079664)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0079666)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0094924)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0094947)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)) (PathBank: SMP0071873)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0071877)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) (PathBank: SMP0079659)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0079663)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0079665)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0079670)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)) (PathBank: SMP0071870)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0071882)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0071886)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0071887)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099816)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099819)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0071884)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085409)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085411)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085412)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0) (PathBank: SMP0099817)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) (PathBank: SMP0099818)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0) (PathBank: SMP0099820)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) (PathBank: SMP0099821)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:0/22:0) (PathBank: SMP0099822)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:0/22:1(13Z)) (PathBank: SMP0099823)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:1(13Z)) (PathBank: SMP0099824)
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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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PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 5458.3 | Standard polar | 33892256 | PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 4702.3 | Standard non polar | 33892256 | PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 5601.0 | Semi standard non polar | 33892256 |
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Spectra |
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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 - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-19 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-19 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-19 | 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 - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Positive-QTOF | splash10-004s-3091322700-312f85b42bf1ec92d47d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Positive-QTOF | splash10-004r-4191211300-4834f80064cde30534c3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Positive-QTOF | splash10-0a70-7094103200-113f8084d1a2207ae79c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Negative-QTOF | splash10-0h00-0192110400-7bec53fa9a068c90f51a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Negative-QTOF | splash10-004i-5290100100-85dc9835340af45aac11 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Negative-QTOF | splash10-004i-9020000000-9787334db4a33c8e44f3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Negative-QTOF | splash10-0006-0000000900-56aeff663cc038761162 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Negative-QTOF | splash10-0ufu-0199440900-07440b470b43a225468e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Negative-QTOF | splash10-0ufu-0399440900-8033371ef91b72fbde3a | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.919 +/- 0.137 uM | Adult (>18 years old) | Both | Normal | | details |
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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 | FDB027805 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 24768154 |
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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 | 52927140 |
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PDB ID | Not Available |
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ChEBI ID | 89371 |
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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 | - 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 ]
- 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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