Record Information |
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Version | 5.0 |
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Status | Predicted |
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Creation Date | 2021-09-22 01:01:58 UTC |
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Update Date | 2021-10-01 16:55:00 UTC |
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HMDB ID | HMDB0301562 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA |
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Description | 3-[(1s,2r,5s)-5-hydroxy-2-[(1e,3s,5z,8z,11z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a 3-[(1S_2R_5S)-5-hydroxy-2-[(1E_3S_5Z_8Z_11Z)-3-hydroxytetradeca-1_5_8_11-tetraen-1-yl]-3-oxocyclopentyl]propanoic acid thioester of coenzyme A. 3-[(1s,2r,5s)-5-hydroxy-2-[(1e,3s,5z,8z,11z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-coa is an acyl-CoA with 22 fatty acid group as the acyl moiety attached to coenzyme A. Coenzyme A was discovered in 1946 by Fritz Lipmann (Journal of Biological Chemistry (1946) 162 (3): 743–744) and its structure was determined in the early 1950s at the Lister Institute in London. Coenzyme A is a complex, thiol-containing molecule that is naturally synthesized from pantothenate (vitamin B5), which is found in various foods such as meat, vegetables, cereal grains, legumes, eggs, and milk. More specifically, coenzyme A (CoASH or CoA) consists of a beta-mercaptoethylamine group linked to the vitamin pantothenic acid (B5) through an amide linkage and 3'-phosphorylated ADP. Coenzyme A is synthesized in a five-step process that requires four molecules of ATP, pantothenate and cysteine. It is believed that there are more than 1100 types of acyl-CoA’s in the human body, which also corresponds to the number of acylcarnitines in the human body. Acyl-CoAs exists in all living species, ranging from bacteria to plants to humans. The general role of acyl-CoA’s is to assist in transferring fatty acids from the cytoplasm to mitochondria. This process facilitates the production of fatty acids in cells, which are essential in cell membrane structure. Acyl-CoA's are also susceptible to beta oxidation, forming, ultimately, acetyl-CoA. Acetyl-CoA can enter the citric acid cycle, eventually forming several equivalents of ATP. In this way, fats are converted to ATP -- or biochemical energy. Acyl-CoAs can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain acyl-CoAs; 2) medium-chain acyl-CoAs; 3) long-chain acyl-CoAs; and 4) very long-chain acyl-CoAs; 5) hydroxy acyl-CoAs; 6) branched chain acyl-CoAs; 7) unsaturated acyl-CoAs; 8) dicarboxylic acyl-CoAs and 9) miscellaneous acyl-CoAs. Short-chain acyl-CoAs have acyl-groups with two to four carbons (C2-C4), medium-chain acyl-CoAs have acyl-groups with five to eleven carbons (C5-C11), long-chain acyl-CoAs have acyl-groups with twelve to twenty carbons (C12-C20) while very long-chain acyl-CoAs have acyl groups with more than 20 carbons. 3-[(1s,2r,5s)-5-hydroxy-2-[(1e,3s,5z,8z,11z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-coa is therefore classified as a very long chain acyl-CoA. The oxidative degradation of fatty acids is a two-step process, catalyzed by acyl-CoA synthetase/synthase. Fatty acids are first converted to their acyl phosphate, the precursor to acyl-CoA. The latter conversion is mediated by acyl-CoA synthase. Three types of acyl-CoA synthases are employed, depending on the chain length of the fatty acid. 3-[(1s,2r,5s)-5-hydroxy-2-[(1e,3s,5z,8z,11z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-coa, being a very long chain acyl-CoA is a substrate for very long chain acyl-CoA synthase. The second step of fatty acid degradation is beta oxidation. Beta oxidation occurs in mitochondria and, in the case of very long chain acyl-CoAs, the peroxisome. After its formation in the cytosol, 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA into 3-[(1S_2R_5S)-5-hydroxy-2-[(1E_3S_5Z_8Z_11Z)-3-hydroxytetradeca-1_5_8_11-tetraen-1-yl]-3-oxocyclopentyl]propanoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, 3-[(1S_2R_5S)-5-hydroxy-2-[(1E_3S_5Z_8Z_11Z)-3-hydroxytetradeca-1_5_8_11-tetraen-1-yl]-3-oxocyclopentyl]propanoylcarnitine is converted back to 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA occurs in four steps. First, since 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA is a very long chain acyl-CoA it is the substrate for a very long chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA, creating a double bond between the alpha and beta carbons. FAD is the hydrogen acceptor, yielding FADH2. Second, Enoyl-CoA hydrase catalyzes the addition of water across the newly formed double bond to make an alcohol. Third, 3-hydroxyacyl-CoA dehydrogenase oxidizes the alcohol group to a ketone and NADH is produced from NAD+. Finally, Thiolase cleaves between the alpha carbon and ketone to release one molecule of acetyl-CoA and a new acyl-CoA which is now 2 carbons shorter. This four-step process repeats until 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA has had all its carbons removed from the chain, leaving only acetyl-CoA. Beta oxidation, as well as alpha-oxidation, also occurs in the peroxisome. The peroxisome handles beta oxidation of fatty acids that have more than 20 carbons in their chain because the peroxisome contains very-long-chain Acyl-CoA synthetases and dehydrogenases. The heart primarily metabolizes fat for energy and Acyl-CoA metabolism has been identified as a critical molecule in early-stage heart muscle pump failure. Cellular acyl-CoA content also correlates with insulin resistance, suggesting that it can mediate lipotoxicity in non-adipose tissues. Acyl-CoA: diacylglycerol acyltransferase (DGAT) plays an important role in energy metabolism on account of key enzyme in triglyceride biosynthesis. The study of acyl-CoAs is an active area of research and it is likely that many novel acyl-CoAs will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules. |
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Structure | CCC=CCC=CCC=CCC(O)C=CC1C(CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2OP(O)(O)=O)N2C=NC3=C2N=CN=C3N)C(O)CC1=O InChI=1S/C43H66N7O20P3S/c1-4-5-6-7-8-9-10-11-12-13-27(51)14-15-28-29(31(53)22-30(28)52)16-17-34(55)74-21-20-45-33(54)18-19-46-41(58)38(57)43(2,3)24-67-73(64,65)70-72(62,63)66-23-32-37(69-71(59,60)61)36(56)42(68-32)50-26-49-35-39(44)47-25-48-40(35)50/h5-6,8-9,11-12,14-15,25-29,31-32,36-38,42,51,53,56-57H,4,7,10,13,16-24H2,1-3H3,(H,45,54)(H,46,58)(H,62,63)(H,64,65)(H2,44,47,48)(H2,59,60,61) |
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Synonyms | Value | Source |
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4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-(2-{[2-({3-[5-hydroxy-2-(3-hydroxytetradeca-1,5,8,11-tetraen-1-yl)-3-oxocyclopentyl]propanoyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidate | Generator | 4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-(2-{[2-({3-[5-hydroxy-2-(3-hydroxytetradeca-1,5,8,11-tetraen-1-yl)-3-oxocyclopentyl]propanoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidate | Generator | 4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-(2-{[2-({3-[5-hydroxy-2-(3-hydroxytetradeca-1,5,8,11-tetraen-1-yl)-3-oxocyclopentyl]propanoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidic acid | Generator |
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Chemical Formula | C43H66N7O20P3S |
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Average Molecular Weight | 1126.01 |
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Monoisotopic Molecular Weight | 1125.329619721 |
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IUPAC Name | {[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-3-[(2-{[2-({3-[5-hydroxy-2-(3-hydroxytetradeca-1,5,8,11-tetraen-1-yl)-3-oxocyclopentyl]propanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid |
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Traditional Name | [5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-[(2-{[2-({3-[5-hydroxy-2-(3-hydroxytetradeca-1,5,8,11-tetraen-1-yl)-3-oxocyclopentyl]propanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | CCC=CCC=CCC=CCC(O)C=CC1C(CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2OP(O)(O)=O)N2C=NC3=C2N=CN=C3N)C(O)CC1=O |
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InChI Identifier | InChI=1S/C43H66N7O20P3S/c1-4-5-6-7-8-9-10-11-12-13-27(51)14-15-28-29(31(53)22-30(28)52)16-17-34(55)74-21-20-45-33(54)18-19-46-41(58)38(57)43(2,3)24-67-73(64,65)70-72(62,63)66-23-32-37(69-71(59,60)61)36(56)42(68-32)50-26-49-35-39(44)47-25-48-40(35)50/h5-6,8-9,11-12,14-15,25-29,31-32,36-38,42,51,53,56-57H,4,7,10,13,16-24H2,1-3H3,(H,45,54)(H,46,58)(H,62,63)(H,64,65)(H2,44,47,48)(H2,59,60,61) |
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InChI Key | PWLSCWVUZUYXQQ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Classification | Not classified |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | Not Available |
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Role | Not Available |
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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 Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA 10V, Positive-QTOF | splash10-0a6u-3900000001-74864849a4b9f1eec4c1 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA 20V, Positive-QTOF | splash10-0543-9800000023-6e131ac12aa1f8fa18a9 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA 40V, Positive-QTOF | splash10-014i-0200059000-ebc40344cef539b93db6 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA 10V, Negative-QTOF | splash10-00di-0900000001-bf083b032655b56c83a5 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA 20V, Negative-QTOF | splash10-0a4r-9600100111-cd3d0e42d6570da943f2 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-[(1S,2R,5S)-5-hydroxy-2-[(1E,3S,5Z,8Z,11Z)-3-hydroxytetradeca-1,5,8,11-tetraen-1-yl]-3-oxocyclopentyl]propanoyl-CoA 40V, Negative-QTOF | splash10-0fic-9201201200-cc5b41e8f70cf8afee24 | 2021-10-21 | Wishart Lab | View Spectrum |
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