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Identification |
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YMDB ID | YMDB05629 |
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Name | CL(12:0/15:0/15:0/18:1(9Z)) |
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Species | Saccharomyces cerevisiae |
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Strain | Brewer's yeast |
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Description | CL(12:0/15:0/15:0/18:1(9Z)) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(12:0/15:0/15:0/18:1(9Z)) contains one chain of dodecanoic acid at the C1 position, two chains of pentadecanoic acid at the C2 and C3 positions, one chain of (9Z-octadecenoyl) 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: 1295.746 Monoisotopic: 1294.893976786 |
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InChI Key | HDLKOSZPGFKHOD-NKGZKSAMSA-N |
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InChI | InChI=1S/C69H132O17P2/c1-5-9-13-17-21-25-28-31-32-33-36-40-44-48-52-56-69(74)86-65(60-80-67(72)54-50-46-42-38-34-29-26-22-18-14-10-6-2)62-84-88(77,78)82-58-63(70)57-81-87(75,76)83-61-64(59-79-66(71)53-49-45-41-37-24-20-16-12-8-4)85-68(73)55-51-47-43-39-35-30-27-23-19-15-11-7-3/h31-32,63-65,70H,5-30,33-62H2,1-4H3,(H,75,76)(H,77,78)/b32-31-/t63-,64+,65+/m0/s1 |
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IUPAC Name | [(2S)-3-({[(2R)-3-(dodecanoyloxy)-2-(pentadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy]phosphinic acid |
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Traditional IUPAC Name | (2S)-3-{[(2R)-3-(dodecanoyloxy)-2-(pentadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy)phosphinic acid |
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Chemical Formula | C69H132O17P2 |
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SMILES | [H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as cardiolipins. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,2-diacylglycerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains. |
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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 | Glycerophosphoglycerophosphoglycerols |
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Direct Parent | Cardiolipins |
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Alternative Parents | |
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Substituents | - Cardiolipin
- Tetracarboxylic acid or derivatives
- Dialkyl phosphate
- Fatty acid ester
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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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(12:0/15:0/15:0/18:1(9Z)) | PW006805 | |
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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 | splash10-001m-0493240000-3d1290780aaa433ca303 | 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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