Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2008-12-10 02:05:51 UTC |
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Update Date | 2022-11-30 19:03:55 UTC |
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HMDB ID | HMDB0011222 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) |
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Description | Phosphatidylcholines are a class of phospholipids which incorporate choline as a headgroup. They are a major component of biological membranes and can be isolated from either egg yolk (in Greek lekithos) or soy beans from which they are mechanically extracted or chemically extracted using hexane. Phosphatidylcholines are such a major component of lecithin, that, in some contexts, the terms are sometime used as synonyms. However, lecithin extract consists of a mixture of phosphatidylcholine and other compounds. It is also used along with sodium taurocholate for simulating fed- and fasted-state biorelevant media in dissolution studies of highly-lipophilic drugs. Phosphatidylcholine is a major constituent of cell membranes, and also plays a role in membrane-mediated cell signalling. Phospholipase D catalyzes the hydrolysis of phosphatidylcholine to form phosphatidic acid (PA), releasing the soluble choline headgroup into the cytosol. Some medical researchers are experimenting with using Phosphatidylcholine in a type of injection that will break down fat cells; to be used as an alternative to liposuction known as Injection lipolysis. (Wikipedia). 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. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. |
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Structure | CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C44H78NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-44(46)52-43(42-51-53(47,48)50-40-38-45(3,4)5)41-49-39-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,24-25,29,31,36,39,43H,6-7,9,11-13,15,17-19,21,23,26-28,30,32-35,37-38,40-42H2,1-5H3/b10-8-,16-14-,22-20-,25-24-,31-29-,39-36-/t43-/m1/s1 |
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Synonyms | Value | Source |
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Glycerophosphocholine | HMDB | 1-(1Z-Hexadecenyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholine | HMDB | Glycerophosphocholine(p-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) | HMDB | Lecithin | HMDB | PC(20:5) | HMDB | Gpcho(20:5) | HMDB | Phosphatidylcholine(20:5) | HMDB | PC(p-16:0/20:5) | HMDB | Gpcho(p-16:0/20:5) | HMDB | Phosphatidylcholine(p-16:0/20:5) | HMDB | 1-(1Z-Hexadecenyl)-2-eicosapentaenoyl-GPC | HMDB | 1-(1Z-Hexadecenyl)-2-eicosapentaenoyl-sn-glycero-3-phosphocholine | HMDB | 1-(1Z-Hexadecenyl)-2-eicosapentaenoyl-sn-glycero-phosphatidylcholine | HMDB | GPC(16:1/20:5) | HMDB | GPC(36:6) | HMDB | GPC(O-16:1(1Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | HMDB | GPC(O-16:1(1Z)/20:5n3) | HMDB | GPC(O-16:1(1Z)/20:5W3) | HMDB | GPC(p-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) | HMDB | GPC(p-16:0/20:5n3) | HMDB | GPC(p-16:0/20:5W3) | HMDB | GPCho(16:1/20:5) | HMDB | GPCho(36:6) | HMDB | GPCho(O-16:1(1Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | HMDB | GPCho(O-16:1(1Z)/20:5n3) | HMDB | GPCho(O-16:1(1Z)/20:5W3) | HMDB | GPCho(p-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) | HMDB | GPCho(p-16:0/20:5n3) | HMDB | GPCho(p-16:0/20:5W3) | HMDB | PC(16:1/20:5) | HMDB | PC(36:6) | HMDB | PC(O-16:1(1Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | HMDB | PC(O-16:1(1Z)/20:5n3) | HMDB | PC(O-16:1(1Z)/20:5W3) | HMDB | PC(p-16:0/20:5n3) | HMDB | PC(p-16:0/20:5W3) | HMDB | Phosphatidylcholine(16:1/20:5) | HMDB | Phosphatidylcholine(36:6) | HMDB | Phosphatidylcholine(O-16:1(1Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | HMDB | Phosphatidylcholine(O-16:1(1Z)/20:5n3) | HMDB | Phosphatidylcholine(O-16:1(1Z)/20:5W3) | HMDB | Phosphatidylcholine(p-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) | HMDB | Phosphatidylcholine(p-16:0/20:5n3) | HMDB | Phosphatidylcholine(p-16:0/20:5W3) | HMDB |
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Chemical Formula | C44H78NO7P |
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Average Molecular Weight | 764.0664 |
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Monoisotopic Molecular Weight | 763.551590367 |
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IUPAC Name | (2-{[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
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Traditional Name | (2-{[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)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/C44H78NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-44(46)52-43(42-51-53(47,48)50-40-38-45(3,4)5)41-49-39-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h8,10,14,16,20,22,24-25,29,31,36,39,43H,6-7,9,11-13,15,17-19,21,23,26-28,30,32-35,37-38,40-42H2,1-5H3/b10-8-,16-14-,22-20-,25-24-,31-29-,39-36-/t43-/m1/s1 |
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InChI Key | OEZJTMNFEIOILN-ACTKFRKUSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acyl-glycerophosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position. |
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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 | Glycerophosphocholines |
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Direct Parent | 1-(1Z-alkenyl),2-acyl-glycerophosphocholines |
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Alternative Parents | |
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Substituents | - 1-(1z-alkenyl),2-acyl-glycerophosphocholine
- Phosphocholine
- Glycerol vinyl ether
- Fatty acid ester
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Quaternary ammonium salt
- Tetraalkylammonium salt
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Amine
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic salt
- 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 | Not Available |
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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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PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) | CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5626.9 | Standard polar | 33892256 | PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) | CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 4430.2 | Standard non polar | 33892256 | PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) | CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5067.5 | Semi standard non 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 - PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Positive-QTOF | splash10-03di-0000000900-02671b0c451109667518 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Positive-QTOF | splash10-01q9-0900000500-84937171e27072e1cad3 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Positive-QTOF | splash10-06si-0500210900-0e9a974e38e141c9eefd | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Negative-QTOF | splash10-0002-0000000900-0b3addbc4a30e889b9bc | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Negative-QTOF | splash10-0002-0000000900-0b3addbc4a30e889b9bc | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Negative-QTOF | splash10-0002-0004921700-33864ee71ef59ae7b228 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Negative-QTOF | splash10-03di-0000000900-5e879d0a64a34ebf5084 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Negative-QTOF | splash10-03di-0021010900-8b294e8bd90868700fb8 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(P-16:0/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Negative-QTOF | splash10-0ufr-4194100000-2496c3d43e9ceacbe146 | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 54.193 +/- 1.620 uM | Adult (>18 years old) | Both | Normal (Upper Limit) | Concentration data updated from parsing Nick's... | Blood | 0.409 +/- 0.070 uM | Adult (>18 years old) | Both | Normal (Most Probable) | Concentration data updated from parsing Nick's... |
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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 | FDB027977 |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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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 | 52923910 |
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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 | - 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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