Record Information |
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Version | 5.0 |
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Status | Predicted |
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Creation Date | 2021-12-18 01:17:08 UTC |
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Update Date | 2022-11-30 20:15:29 UTC |
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HMDB ID | HMDB0313203 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | CL(18:0/18:2(9Z,12Z)/20:2(11Z,14Z)/14:0) |
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Description | CL(18:0/18:2(9Z,12Z)/20:2(11Z,14Z)/14:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(18:0/18:2(9Z,12Z)/20:2(11Z,14Z)/14:0) contains one chain of octadecanoic acid at the C1 position, one chain of (9Z,12Z-octadecadienoyl) at the C2 position, one chain of (11Z,14Z-eicosadienoyl) at the C3 position, one chain of tetradecanoic acid at the C4 position 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 will 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 ). Tafazzin is an important enzyme in the remodeling of cardiolipins, and opposite to cardiolipin synthase, it shows strong acyl specificity. This suggest that the specificity in cardiolipin composition is achieved through the remodeling steps. Mutation in the tafazzin gene disrupts the remodeling of cardiolipin and is the cause of Barth syndrome (BTHS), an X-linked human disease (PMID: 16973164 ). BTHS patients seems to lack acyl specificity and as a result, there are many potential cardiolipin species that can exists (PMID: 16226238 ). Common fatty acyl chains determined through methods such as gas chromatography and high-performance liquid chromatography are used to generate various cardiolipins and a representative molecule is chosen from each variation. |
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Structure | [H][C@@](COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(=O)OC[C@H](O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCCCCCCCC InChI=1S/C79H146O17P2/c1-5-9-13-17-21-25-29-32-35-36-39-41-45-48-52-56-60-64-77(82)89-69-74(95-78(83)65-61-57-53-49-43-28-24-20-16-12-8-4)71-93-97(85,86)91-67-73(80)68-92-98(87,88)94-72-75(96-79(84)66-62-58-54-50-46-42-38-34-31-27-23-19-15-11-7-3)70-90-76(81)63-59-55-51-47-44-40-37-33-30-26-22-18-14-10-6-2/h21,23,25,27,32,34-35,38,73-75,80H,5-20,22,24,26,28-31,33,36-37,39-72H2,1-4H3,(H,85,86)(H,87,88)/b25-21-,27-23-,35-32-,38-34-/t73-,74+,75+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C79H146O17P2 |
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Average Molecular Weight | 1429.968 |
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Monoisotopic Molecular Weight | 1429.003527237 |
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IUPAC Name | [(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-2-(tetradecanoyloxy)propoxy]phosphoryl}oxy)propoxy][(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxy]phosphinic acid |
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Traditional Name | (2S)-2-hydroxy-3-{[hydroxy((2R)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-2-(tetradecanoyloxy)propoxy)phosphoryl]oxy}propoxy((2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(=O)OC[C@H](O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C79H146O17P2/c1-5-9-13-17-21-25-29-32-35-36-39-41-45-48-52-56-60-64-77(82)89-69-74(95-78(83)65-61-57-53-49-43-28-24-20-16-12-8-4)71-93-97(85,86)91-67-73(80)68-92-98(87,88)94-72-75(96-79(84)66-62-58-54-50-46-42-38-34-31-27-23-19-15-11-7-3)70-90-76(81)63-59-55-51-47-44-40-37-33-30-26-22-18-14-10-6-2/h21,23,25,27,32,34-35,38,73-75,80H,5-20,22,24,26,28-31,33,36-37,39-72H2,1-4H3,(H,85,86)(H,87,88)/b25-21-,27-23-,35-32-,38-34-/t73-,74+,75+/m0/s1 |
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InChI Key | VCKZFHNQAAHKKN-NJUNTSNFSA-N |
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Chemical Taxonomy |
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Classification | Not classified |
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Ontology |
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Disposition | |
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Physical Properties |
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State | Not Available |
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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 Kovats Retention IndicesNot Available |
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