Showing metabocard for CL(14:1(9Z)/14:1(9Z)/16:0/24:1(9Z)) (MMDBc0040954)
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| Version | 1.0 | ||||||||||||
| Status | Detected and Quantified | ||||||||||||
| Creation Date | 2021-11-19 10:18:26 UTC | ||||||||||||
| Update Date | 2022-08-31 23:42:25 UTC | ||||||||||||
| Metabolite ID | MMDBc0040954 | ||||||||||||
| Metabolite Identification | |||||||||||||
| Common Name | CL(14:1(9Z)/14:1(9Z)/16:0/24:1(9Z)) | ||||||||||||
| Description | CL(14:1(9Z)/14:1(9Z)/16:0/24:1(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(14:1(9Z)/14:1(9Z)/16:0/24:1(9Z)) contains two chains of (9Z-tetradecenoyl) at the C1 and C2 positions, one chain of hexadecanoic acid at the C3 position, one chain of (9Z-tetracosenoyl) 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. | ||||||||||||
| Structure |  | ||||||||||||
| Synonyms | Not Available | ||||||||||||
| Molecular Formula | C77H144O17P2 | ||||||||||||
| Average Mass | 1403.93 | ||||||||||||
| Monoisotopic Mass | 1402.987877173 | ||||||||||||
| IUPAC Name | Not Available | ||||||||||||
| Traditional Name | Not Available | ||||||||||||
| CAS Registry Number | Not Available | ||||||||||||
| SMILES | Not Available | ||||||||||||
| InChI Identifier | InChI=1S/C77H144O17P2/c1-5-9-13-17-21-25-29-31-32-33-34-35-36-37-38-40-44-48-52-56-60-64-77(82)94-73(68-88-75(80)62-58-54-50-46-43-39-30-26-22-18-14-10-6-2)70-92-96(85,86)90-66-71(78)65-89-95(83,84)91-69-72(93-76(81)63-59-55-51-47-42-28-24-20-16-12-8-4)67-87-74(79)61-57-53-49-45-41-27-23-19-15-11-7-3/h19-20,23-24,37-38,71-73,78H,5-18,21-22,25-36,39-70H2,1-4H3,(H,83,84)(H,85,86)/b23-19-,24-20-,38-37-/t71-,72+,73+/m0/s1 | ||||||||||||
| InChI Key | VGQGDIHBDGJWJT-NYKQVIGZSA-N | ||||||||||||
| Chemical Taxonomy | |||||||||||||
| 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. | ||||||||||||
| Kingdom | Organic compounds | ||||||||||||
| Super Class | Lipids and lipid-like molecules | ||||||||||||
| Class | Glycerophospholipids | ||||||||||||
| Sub Class | Glycerophosphoglycerophosphoglycerols | ||||||||||||
| Direct Parent | Cardiolipins | ||||||||||||
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| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||
| External Descriptors | Not Available | ||||||||||||
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| Physical Properties | |||||||||||||
| State | Solid | ||||||||||||
| Predicted Properties | Not Available | ||||||||||||
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| Cellular Locations | Not Available | ||||||||||||
| Biospecimen Locations | Not Available | ||||||||||||
| Tissue Locations | Not Available | ||||||||||||
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| HMDB ID | Not Available | ||||||||||||
| DrugBank ID | Not Available | ||||||||||||
| Phenol Explorer Compound ID | Not Available | ||||||||||||
| FooDB ID | Not Available | ||||||||||||
| KNApSAcK ID | Not Available | ||||||||||||
| Chemspider ID | Not Available | ||||||||||||
| KEGG Compound ID | Not Available | ||||||||||||
| BioCyc ID | Not Available | ||||||||||||
| BiGG ID | Not Available | ||||||||||||
| Wikipedia Link | Not Available | ||||||||||||
| METLIN ID | Not Available | ||||||||||||
| PubChem Compound | Not Available | ||||||||||||
| PDB ID | Not Available | ||||||||||||
| ChEBI ID | Not Available | ||||||||||||
| Food Biomarker Ontology | Not Available | ||||||||||||
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| Synthesis Reference | Not Available | ||||||||||||
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