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Identification |
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YMDB ID | YMDB08022 |
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Name | CL(14:1(11Z)/14:1(9Z)/16:0/26:1(11Z)) |
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Species | Saccharomyces cerevisiae |
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Strain | Brewer's yeast |
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Description | CL(14:1(11Z)/14:1(9Z)/16:0/26:1(11Z)) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(14:1(11Z)/14:1(9Z)/16:0/26:1(11Z)) contains one chain of (11Z-tetradecenoyl) at the C1 position, one chain of (9Z-tetradecenoyl) at the C2 position, one chain of hexadecanoic acid at the C3 position, one chain of (11Z-hexacosenoyl) at the C4 position. While the theoretical charge of cardiolipins is -2, under normal physiological conditions (pH near 7), the molecule may carry only one negative charge. In prokaryotes such as E. coli, the enzyme known as diphosphatidylglycerol synthase catalyses the transfer of the phosphatidyl moiety of one phosphatidylglycerol to the free 3'-hydroxyl group of another, with the elimination of one molecule of glycerol. In E. coli, which acylates its glycerophospholipids with acyl chains ranging in length from 12 to 18 carbons and possibly containing an unsaturation, or a cyclopropane group more than 100 possible CL molecular species are theoretically possible, 53 of these species having been characterized. E. coli membranes consist of ~5% cardiolipin (CL), 20-25% phosphatidylglycerol (PG), and 70-80% phosphatidylethanolamine (PE) as well as smaller amounts of phosphatidylserine (PS). CL is distributed between the two leaflets of the bilayers and is located preferentially at the poles and septa in E. coli and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in E. coli is dependent on CL. It is believed that cell shape may influence the localization of CL and the localization of certain membrane proteins. |
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Structure | |
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Synonyms | Not Available |
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CAS number | Not Available |
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Weight | Average: 1431.984 Monoisotopic: 1431.019177302 |
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InChI Key | ZJZGTVTWVOXCMX-NZDHGSPASA-N |
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InChI | InChI=1S/C79H148O17P2/c1-5-9-13-17-21-25-29-31-32-33-34-35-36-37-38-39-40-42-46-50-54-58-62-66-79(84)96-75(70-90-77(82)64-60-56-52-48-45-41-30-26-22-18-14-10-6-2)72-94-98(87,88)92-68-73(80)67-91-97(85,86)93-71-74(95-78(83)65-61-57-53-49-44-28-24-20-16-12-8-4)69-89-76(81)63-59-55-51-47-43-27-23-19-15-11-7-3/h11,15,20,24,36-37,73-75,80H,5-10,12-14,16-19,21-23,25-35,38-72H2,1-4H3,(H,85,86)(H,87,88)/b15-11-,24-20-,37-36-/t73-,74+,75+/m0/s1 |
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IUPAC Name | [(2R)-3-({[(2R)-2-[(12Z)-hexacos-12-enoyloxy]-3-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-3-[(11Z)-tetradec-11-enoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propoxy]phosphinic acid |
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Traditional IUPAC Name | (2R)-3-{[(2R)-2-[(12Z)-hexacos-12-enoyloxy]-3-(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-3-[(11Z)-tetradec-11-enoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propoxy)phosphinic acid |
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Chemical Formula | C79H148O17P2 |
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SMILES | [H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCC\C=C/CCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CC)OC(=O)CCCCCCC\C=C/CCCC |
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Chemical Taxonomy |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | Cardiolipin Biosynthesis CL(14:1(11Z)/14:1(9Z)/16:0/26:1(11Z)) | PW009584 | |
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KEGG Pathways | Not Available |
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SMPDB Reactions | |
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KEGG Reactions | Not Available |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-06vo-0098042000-d7eb3ac58d09807d05fd | JSpectraViewer |
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References |
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References: | - Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
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Synthesis Reference: | Not Available |
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External Links: | Resource | Link |
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CHEBI ID | Not Available | HMDB ID | Not Available | Pubchem Compound ID | Not Available | Kegg ID | Not Available | ChemSpider ID | Not Available | FOODB ID | Not Available | Wikipedia ID | Not Available | BioCyc ID | Not Available |
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