Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-08-25 08:48:07 UTC |
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Update Date | 2019-07-23 09:13:06 UTC |
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HMDB ID | HMDB0111865 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CL(20:4(5Z,8Z,11Z,14Z)/16:0/16:0/16:0) |
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Description | CL(20:4(5Z,8Z,11Z,14Z)/16:0/16:0/16:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(20:4(5Z,8Z,11Z,14Z)/16:0/16:0/16:0) contains one chain of (5Z,8Z,11Z,14Z-eicosatetraenoyl) at the C1 position, three chains of hexadecanoic acid at the C2, C3 and C4 positions. 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 | Value | Source |
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CL(20:4/16:0/16:0/16:0) | Lipid Annotator, HMDB | Cardiolipin(20:4/16:0/16:0/16:0) | Lipid Annotator, HMDB | 1'-[1-arachidonoyl-2-palmitoyl-sn-glycero-3-phospho],3'-[1,2-dipalmitoyl-rac-glycero-3-phospho]-glycerol | Lipid Annotator, HMDB | CL(1'-[20:4(5Z,8Z,11Z,14Z)/16:0],3'-[16:0/16:0]) | Lipid Annotator, HMDB | Cardiolipin(68:4) | Lipid Annotator, HMDB | CL(20:4(5Z,8Z,11Z,14Z)/16:0/16:0/16:0) | Lipid Annotator | 1'-[1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-hexadecanoyl-sn-glycero-3-phospho],3'-[1,2-dihexadecanoyl-rac-glycero-3-phospho]-glycerol | Lipid Annotator, HMDB | CL(68:4) | Lipid Annotator, HMDB |
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Chemical Formula | C77H142O17P2 |
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Average Molecular Weight | 1401.914 |
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Monoisotopic Molecular Weight | 1400.972227108 |
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IUPAC Name | [(2R)-3-({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphinic acid |
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Traditional Name | (2R)-3-{[(2R)-2,3-bis(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-(hexadecanoyloxy)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C77H142O17P2/c1-5-9-13-17-21-25-29-33-34-35-36-40-42-46-50-54-58-62-75(80)88-68-73(94-77(82)64-60-56-52-48-44-39-32-28-24-20-16-12-8-4)70-92-96(85,86)90-66-71(78)65-89-95(83,84)91-69-72(93-76(81)63-59-55-51-47-43-38-31-27-23-19-15-11-7-3)67-87-74(79)61-57-53-49-45-41-37-30-26-22-18-14-10-6-2/h21,25,33-34,36,40,46,50,71-73,78H,5-20,22-24,26-32,35,37-39,41-45,47-49,51-70H2,1-4H3,(H,83,84)(H,85,86)/b25-21-,34-33-,40-36-,50-46-/t71-,72-,73-/m1/s1 |
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InChI Key | ZEXMKVRSHXLZMD-JTDLGHPOSA-N |
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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
- Fatty acid ester
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Organooxygen compound
- Alcohol
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Organoleptic effect: |
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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | |
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General References | - Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. doi: 10.1194/jlr.M009449. Epub 2010 Jul 29. [PubMed:20671299 ]
- Lopez-Lopez A, Lopez-Sabater MC, Campoy-Folgoso C, Rivero-Urgell M, Castellote-Bargallo AI: Fatty acid and sn-2 fatty acid composition in human milk from Granada (Spain) and in infant formulas. Eur J Clin Nutr. 2002 Dec;56(12):1242-54. [PubMed:12494309 ]
- Jenkins B, West JA, Koulman A: A review of odd-chain fatty acid metabolism and the role of pentadecanoic Acid (c15:0) and heptadecanoic Acid (c17:0) in health and disease. Molecules. 2015 Jan 30;20(2):2425-44. doi: 10.3390/molecules20022425. [PubMed:25647578 ]
- Kingsbury KJ, Morgan DM: The analysis of the fatty acids of normal human depot fat by gas-liquid chromatography. Biochem J. 1964 Jan;90(1):140-7. [PubMed:5832283 ]
- Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- 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 ]
- Schlame M, Ren M: The role of cardiolipin in the structural organization of mitochondrial membranes. Biochim Biophys Acta. 2009 Oct;1788(10):2080-3. doi: 10.1016/j.bbamem.2009.04.019. Epub 2009 May 4. [PubMed:19413994 ]
- 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 ]
- Schlame M, Rua D, Greenberg ML: The biosynthesis and functional role of cardiolipin. Prog Lipid Res. 2000 May;39(3):257-88. [PubMed:10799718 ]
- McMillin JB, Dowhan W: Cardiolipin and apoptosis. Biochim Biophys Acta. 2002 Dec 30;1585(2-3):97-107. [PubMed:12531542 ]
- Houtkooper RH, Vaz FM: Cardiolipin, the heart of mitochondrial metabolism. Cell Mol Life Sci. 2008 Aug;65(16):2493-506. doi: 10.1007/s00018-008-8030-5. [PubMed:18425414 ]
- 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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