Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-04-06 16:20:42 UTC |
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Update Date | 2022-03-07 02:51:22 UTC |
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HMDB ID | HMDB0012188 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | all-trans-Hexaprenyl diphosphate |
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Description | all-trans-Hexaprenyl diphosphate is the final product of the hexaprenyl diphosphate biosynthesis pathway. In this pathway, multiple units of isopentenyl diphosphate (IPP) undergo a series of polymerizations to form various polyisoprenoids. There are two different pathways for the biosynthesis of IPP. Bacteria that possess ubiquinone generally use the methylerythritol phosphate pathway (MEP), while the eukaryotic microorganisms use the mevalonate pathway. However, exceptions exist. For example, some eukaryotic microbes, like the green algae and the malarial parasite Plasmodium falciparum, appear to utilize the MEP pathway, and some bacteria utilize the mevalonate pathway (Eisenreich01, Eisenreich04). In Saccharomyces cerevisiae S288C, the initial addition of two isoprenyl units to form (E, E)-farnesyl diphosphate is catalyzed by geranyltransferase / dimethylallyltransferase, encoded by FPP1. An additional unit is added by farnesyltranstransferase (encoded by BTS1), resulting in the formation of all-trans-geranyl-geranyl diphosphate. The last enzyme in this pathway is hexaprenyl diphosphate synthase (encoded by COQ1), which adds additional isoprenoid units to a maximal length unique to the organism. In the case of Saccharomyces cerevisiae S288C, it is 6 units. Polyprenyl diphosphate synthase enzymes, such as hexaprenyl diphosphate synthase, are responsible for determining the final length of the tail. When yeast COQ1 mutants are complemented with homologs from other organisms, ubiquinone biosynthesis is restored, but the tail length of the quinone depends on the source of the enzyme. |
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Structure | CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O InChI=1S/C30H52O7P2/c1-25(2)13-8-14-26(3)15-9-16-27(4)17-10-18-28(5)19-11-20-29(6)21-12-22-30(7)23-24-36-39(34,35)37-38(31,32)33/h13,15,17,19,21,23H,8-12,14,16,18,20,22,24H2,1-7H3,(H,34,35)(H2,31,32,33)/b26-15+,27-17+,28-19+,29-21+,30-23+ |
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Synonyms | Value | Source |
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(2E,6E,10E,14E,18E)-3,7,11,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl trihydrogen diphosphate | ChEBI | (2E,6E,10E,14E,18E)-3,7,11,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl trihydrogen diphosphoric acid | Generator | all-trans-Hexaprenyl diphosphoric acid | Generator | (E)-Hexaprenyl diphosphate | HMDB |
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Chemical Formula | C30H52O7P2 |
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Average Molecular Weight | 586.6772 |
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Monoisotopic Molecular Weight | 586.318827042 |
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IUPAC Name | [({[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid |
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Traditional Name | {[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]oxy(hydroxy)phosphoryl}oxyphosphonic acid |
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CAS Registry Number | 207513-95-9 |
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SMILES | CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O |
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InChI Identifier | InChI=1S/C30H52O7P2/c1-25(2)13-8-14-26(3)15-9-16-27(4)17-10-18-28(5)19-11-20-29(6)21-12-22-30(7)23-24-36-39(34,35)37-38(31,32)33/h13,15,17,19,21,23H,8-12,14,16,18,20,22,24H2,1-7H3,(H,34,35)(H2,31,32,33)/b26-15+,27-17+,28-19+,29-21+,30-23+ |
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InChI Key | NGFSMHKFTZROKJ-MMSZMYIBSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Polyprenols |
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Direct Parent | Bactoprenol diphosphates |
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Alternative Parents | |
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Substituents | - Bactoprenol diphosphate
- Polyprenyl diphosphate
- Polyprenyl monophosphate
- Sesterterpenoid
- Organic pyrophosphate
- Isoprenoid phosphate
- Monoalkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- 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 | |
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Role | |
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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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all-trans-Hexaprenyl diphosphate,1TMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O | 4023.6 | Semi standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,1TMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O | 3221.6 | Standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,1TMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O | 4948.9 | Standard polar | 33892256 | all-trans-Hexaprenyl diphosphate,1TMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C | 4022.8 | Semi standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,1TMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C | 3229.9 | Standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,1TMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C | 4971.3 | Standard polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C | 3944.5 | Semi standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C | 3288.5 | Standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C | 4460.4 | Standard polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3946.5 | Semi standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3266.5 | Standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4463.6 | Standard polar | 33892256 | all-trans-Hexaprenyl diphosphate,3TMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3873.1 | Semi standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,3TMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3324.2 | Standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,3TMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3921.4 | Standard polar | 33892256 | all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O | 4206.3 | Semi standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O | 3363.0 | Standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O | 5006.3 | Standard polar | 33892256 | all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 4201.9 | Semi standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 3377.9 | Standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,1TBDMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 5022.1 | Standard polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 4317.6 | Semi standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 3568.5 | Standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #1 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C | 4522.3 | Standard polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4320.4 | Semi standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3537.3 | Standard non polar | 33892256 | all-trans-Hexaprenyl diphosphate,2TBDMS,isomer #2 | CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4554.3 | Standard 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 - all-trans-Hexaprenyl diphosphate GC-MS (Non-derivatized) - 70eV, Positive | splash10-00tb-7466390000-1a091a15f69aa600fd33 | 2017-09-01 | 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 - all-trans-Hexaprenyl diphosphate 10V, Positive-QTOF | splash10-0a4r-0202690000-ca7be5f91d120b34e02f | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 20V, Positive-QTOF | splash10-0a4i-2312910000-a18bd263c2252df7e12b | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 40V, Positive-QTOF | splash10-0a59-4439820000-433602f028fdf8312339 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 10V, Negative-QTOF | splash10-000i-0400090000-eba550c0908e0bdcc04f | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 20V, Negative-QTOF | splash10-056r-7900010000-903a330facd80aef97a7 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 40V, Negative-QTOF | splash10-004i-9000000000-5db7557b14be93fbdd9b | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 10V, Positive-QTOF | splash10-000i-0100290000-dc5d848846327789fd85 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 20V, Positive-QTOF | splash10-0aos-0004930000-e9910289e743569a483c | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 40V, Positive-QTOF | splash10-020a-1925210000-a29abfabad842bde7acf | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 10V, Negative-QTOF | splash10-000i-0000090000-8f206fdd3583884650db | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 20V, Negative-QTOF | splash10-000i-1300190000-fbac398a5a0b0394af5d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - all-trans-Hexaprenyl diphosphate 40V, Negative-QTOF | splash10-056r-9400000000-c2d5c8e79c928bb87206 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | 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 | 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 | FDB028840 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4444089 |
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KEGG Compound ID | C01230 |
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BioCyc ID | ALL-TRANS-HEXAPRENYL-DIPHOSPHATE |
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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 | 5280413 |
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PDB ID | Not Available |
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ChEBI ID | 17528 |
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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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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