| Record Information |
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| Version | 5.0 |
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| Status | Predicted |
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| Creation Date | 2021-09-21 22:39:57 UTC |
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| Update Date | 2021-10-01 16:53:59 UTC |
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| HMDB ID | HMDB0301282 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA |
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| Description | (4e,7e,13e)-hexadeca-4,7,13-trienoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a (4E_7E_13E)-hexadeca-4_7_13-trienoic acid thioester of coenzyme A. (4e,7e,13e)-hexadeca-4,7,13-trienoyl-coa is an acyl-CoA with 1 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. (4e,7e,13e)-hexadeca-4,7,13-trienoyl-coa is therefore classified as a short 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. (4e,7e,13e)-hexadeca-4,7,13-trienoyl-coa, being a short chain acyl-CoA is a substrate for short 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, (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA into (4E_7E_13E)-hexadeca-4_7_13-trienoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, (4E_7E_13E)-hexadeca-4_7_13-trienoylcarnitine is converted back to (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA occurs in four steps. First, since (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA is a short chain acyl-CoA it is the substrate for a short chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of (4E,7E,13E)-hexadeca-4,7,13-trienoyl-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 (4E,7E,13E)-hexadeca-4,7,13-trienoyl-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=CCCCCC=CCC=CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N InChI=1S/C37H60N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h5-6,11-12,14-15,24-26,30-32,36,47-48H,4,7-10,13,16-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52) |
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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)-N-(2-{[2-(hexadeca-4,7,13-trienoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-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)-N-(2-{[2-(hexadeca-4,7,13-trienoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-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)-N-(2-{[2-(hexadeca-4,7,13-trienoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid | Generator |
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| Chemical Formula | C37H60N7O17P3S |
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| Average Molecular Weight | 999.9 |
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| Monoisotopic Molecular Weight | 999.297925668 |
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| IUPAC Name | {[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(hexadeca-4,7,13-trienoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid |
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| Traditional Name | [5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-(hexadeca-4,7,13-trienoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid |
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| CAS Registry Number | Not Available |
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| SMILES | CCC=CCCCCC=CCC=CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N |
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| InChI Identifier | InChI=1S/C37H60N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h5-6,11-12,14-15,24-26,30-32,36,47-48H,4,7-10,13,16-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52) |
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| InChI Key | PCLUVBQEYNLFJR-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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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| MS | Mass Spectrum (Electron Ionization) | Not Available | 2022-08-06 | Not Available | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA 10V, Positive-QTOF | splash10-0udi-9000000001-7b32f73f43d36143864b | 2021-10-21 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA 20V, Positive-QTOF | splash10-000i-2600000329-ccfd6c6062749d82fae0 | 2021-10-21 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA 40V, Positive-QTOF | splash10-0006-0101900000-56815bbdc2bd658ad375 | 2021-10-21 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA 10V, Negative-QTOF | splash10-0002-0000000009-ba3870c5fcee4e5b7452 | 2021-10-21 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA 20V, Negative-QTOF | splash10-0032-4120302419-d3ddda38d43f067c0409 | 2021-10-21 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4E,7E,13E)-hexadeca-4,7,13-trienoyl-CoA 40V, Negative-QTOF | splash10-05r0-2002201209-e4635fd4680480f53971 | 2021-10-21 | Wishart Lab | View Spectrum |
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