Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2008-09-26 12:17:44 UTC |
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Update Date | 2022-11-30 19:03:54 UTC |
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HMDB ID | HMDB0010691 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z)) |
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Description | CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z)) is a cardiolipin (CL). Cardiolipins are sometimes called 'double' phospholipids because they have four fatty acid tails, instead of the usual two. They are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,3-diacylglyerol 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. CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z)) contains four chains of (9Z-octadecenoyl) at the C1, C2, C3 and C4 positions fatty acids. Cardiolipins are known to be present in all mammalian cells, especially cells with a high number of mitochondria. De novo synthesis of Cardiolipins begins with condensing phosphatidic acid (PA) with cytidine-5’-triphosphate (CTP) to form cytidine-diphosphate-1,2-diacyl-sn-glycerol (CDP-DG). Glycerol-3-phosphate is subsequently added to this newly formed CDP-DG molecule to form phosphatidylglycerol phosphate (PGP), which is immediately dephosphorylated to form PG. The final step is the process of condensing the PG molecule with another CDP-DG molecule to form a new cardiolipin, which is catalyzed by cardiolipin synthase. All new cardiolipins immediately undergo a series remodeling resulting in the common cardiolipin compositions. (PMID: 16442164 ). Cardiolipin synthase shows no selectivity for fatty acyl chains used in the de novo synthesis of cardiolipin (PMID: 16442164 ). Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20% of the total lipid. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane and are important for mitochondrial respiratory capacity. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. Tafazzin is an important enzyme in the remodeling of cardiolipins, and in contrast to cardiolipin synthase, it shows strong acyl specificity. This suggests that the specificity in cardiolipin composition is achieved through the remodeling steps. Mutation in the tafazzin gene disrupts the remodeling of cardiolipins and is the cause of Barth syndrome (BTHS), an X-linked human disease (PMID: 16973164 ). BTHS patients seem to lack acyl specificity. As a result, there are many potential cardiolipin species that can exist (PMID: 16226238 ). |
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Structure | [H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C81H150O17P2/c1-5-9-13-17-21-25-29-33-37-41-45-49-53-57-61-65-78(83)91-71-76(97-80(85)67-63-59-55-51-47-43-39-35-31-27-23-19-15-11-7-3)73-95-99(87,88)93-69-75(82)70-94-100(89,90)96-74-77(98-81(86)68-64-60-56-52-48-44-40-36-32-28-24-20-16-12-8-4)72-92-79(84)66-62-58-54-50-46-42-38-34-30-26-22-18-14-10-6-2/h33-40,75-77,82H,5-32,41-74H2,1-4H3,(H,87,88)(H,89,90)/b37-33-,38-34-,39-35-,40-36-/t76-,77-/m1/s1 |
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Synonyms | Value | Source |
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1,1'2,2'-Tetraoleoyl cardiolipin | HMDB | 1,1'2,2'-Tetraoleoylcardiolipin | HMDB | 1,1'2,2'-Tetraoleyl cardiolipin | HMDB | 1,1'2,2'-Tetraoleylcardiolipin | HMDB | Tetraoleoyl cardiolipin | HMDB | Tetraoleoylcardiolipin | HMDB | Tetraoleylcardiolipin | HMDB | Cardiolipin(18:1/18:1/18:1/18:1) | HMDB | Cardiolipin(72:4) | HMDB | CL(72:4) | HMDB | CL(1'-[18:1(9Z)/18:1(9Z)],3'-[18:1(9Z)/18:1(9Z)]) | HMDB | CL(18:1/18:1/18:1/18:1) | HMDB | 1'-[1,2-Di(9Z-octadecenoyl)-rac-glycero-3-phospho],3'-[1,2-di(9Z-octadecenoyl)-rac-glycero-3-phospho]-glycerol | HMDB | 1'-[1,2-Dioleoyl-rac-glycero-3-phospho],3'-[1,2-dioleoyl-rac-glycero-3-phospho]-glycerol | HMDB | 1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phospho-(1'-glycerol) | HMDB | 1-a-Linolenoyl-2-docosahexaenoyl-sn-glycero-3-phosphoglycerol | HMDB | 1-alpha-Linolenoyl-2-docosahexaenoyl-sn-glycero-3-phosphoglycerol | HMDB | GPG(18:3/22:6) | HMDB | GPG(18:3N3/22:6N3) | HMDB | GPG(18:3W3/22:6W3) | HMDB | GPG(40:9) | HMDB | PG(18:3/22:6) | HMDB | PG(18:3N3/22:6N3) | HMDB | PG(18:3W3/22:6W3) | HMDB | PG(40:9) | HMDB | Phosphatidylglycerol(18:3/22:6) | HMDB | Phosphatidylglycerol(18:3n3/22:6n3) | HMDB | Phosphatidylglycerol(18:3W3/22:6W3) | HMDB | Phosphatidylglycerol(40:9) | HMDB | 1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoglycerol | HMDB | CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z)) | Lipid Annotator |
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Chemical Formula | C81H150O17P2 |
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Average Molecular Weight | 1458.022 |
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Monoisotopic Molecular Weight | 1457.034827366 |
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IUPAC Name | [(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy][3-({[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid |
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Traditional Name | tetraoleoyl cardiolipin |
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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)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC |
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InChI Identifier | InChI=1S/C81H150O17P2/c1-5-9-13-17-21-25-29-33-37-41-45-49-53-57-61-65-78(83)91-71-76(97-80(85)67-63-59-55-51-47-43-39-35-31-27-23-19-15-11-7-3)73-95-99(87,88)93-69-75(82)70-94-100(89,90)96-74-77(98-81(86)68-64-60-56-52-48-44-40-36-32-28-24-20-16-12-8-4)72-92-79(84)66-62-58-54-50-46-42-38-34-30-26-22-18-14-10-6-2/h33-40,75-77,82H,5-32,41-74H2,1-4H3,(H,87,88)(H,89,90)/b37-33-,38-34-,39-35-,40-36-/t76-,77-/m1/s1 |
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InChI Key | TWHQNHQPSCPQNY-WVRHUKEESA-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 | |
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Ontology |
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Physiological effect | |
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Disposition | |
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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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 380.691 | 30932474 | DeepCCS | [M-H]- | 378.224 | 30932474 | DeepCCS | [M-2H]- | 412.498 | 30932474 | DeepCCS | [M+Na]+ | 387.873 | 30932474 |
Predicted Kovats Retention IndicesNot Available |
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General References | - 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 ]
- Schlame M, Ren M, Xu Y, Greenberg ML, Haller I: Molecular symmetry in mitochondrial cardiolipins. Chem Phys Lipids. 2005 Dec;138(1-2):38-49. Epub 2005 Sep 7. [PubMed:16226238 ]
- Schlame M, Ren M: Barth syndrome, a human disorder of cardiolipin metabolism. FEBS Lett. 2006 Oct 9;580(23):5450-5. Epub 2006 Jul 17. [PubMed:16973164 ]
- 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 ]
- Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- 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 ]
- Hauff KD, Hatch GM: Cardiolipin metabolism and Barth Syndrome. Prog Lipid Res. 2006 Mar;45(2):91-101. Epub 2006 Jan 18. [PubMed:16442164 ]
- 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 ]
- 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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