Classification Term: 1842
Medium-chain fatty acyl CoAs (ontology term: CHEMONTID:0003206)
Acyl CoAs where the group acylated to the coenzyme A moiety is a medium aliphatic chain of 6 to 12 carbon atoms." []
found 4 associated metabolites at family metabolite taxonomy ontology rank level.
Ancestor: Acyl CoAs
Child Taxonomies: There is no child term of current ontology term.
4-cis-Decenoyl-CoA
cis-4-Decenoyl-CoA is an intermediate of linoleic acid catabolism, degraded by a mitochondrial 4-enoyl-CoA reductase. (PMID: 729581). There are two 2,4-dienoyl-CoA reductases (formerly called 4-enoyl-CoA reductase) in liver, one in mitochondria and another one in peroxisomes. Isolated peroxisomes metabolize 4-cis-decenoyl-CoA via the 2,4-dienoyl-CoA reductase pathway. (PMID: 7263650). cis-4-Decenoyl-CoA is an intermediate of linoleic acid catabolism, degraded by a mitochondrial 4-enoyl-CoA reductase. (PMID: 729581)
(4E)-Undec-4-enoyl-CoA
(4e)-undec-4-enoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a (4E)-undec-4-enoic acid thioester of coenzyme A. (4e)-undec-4-enoyl-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-CoAs 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)-undec-4-enoyl-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)-undec-4-enoyl-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)-Undec-4-enoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of (4E)-Undec-4-enoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts (4E)-Undec-4-enoyl-CoA into (4E)-Undec-4-enoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, (4E)-Undec-4-enoylcarnitine is converted back to (4E)-Undec-4-enoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of (4E)-Undec-4-enoyl-CoA occurs in four steps. First, since (4E)-Undec-4-enoyl-CoA is a short chain acyl-CoA it is the substrate for a short chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of (4E)-Undec-4-enoyl-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 ...
Undec-3-enoyl-CoA
Undec-3-enoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is an undec-3-enoic acid thioester of coenzyme A. Undec-3-enoyl-coa is an acyl-CoA with 11 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-CoAs 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. Undec-3-enoyl-coa is therefore classified as a medium 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. Undec-3-enoyl-coa, being a medium chain acyl-CoA is a substrate for medium 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, Undec-3-enoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of Undec-3-enoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts Undec-3-enoyl-CoA into Undec-3-enoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, Undec-3-enoylcarnitine is converted back to Undec-3-enoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of Undec-3-enoyl-CoA occurs in four steps. First, since Undec-3-enoyl-CoA is a medium chain acyl-CoA it is the substrate for a medium chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of Undec-3-enoyl-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, Thio...
4-Hexenoyl-CoA
4-hexenoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a hex-4-enoic acid thioester of coenzyme A. 4-hexenoyl-coa is an acyl-CoA with 6 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-CoAs 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. 4-hexenoyl-coa is therefore classified as a medium 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. 4-hexenoyl-coa, being a medium chain acyl-CoA is a substrate for medium 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, 4-Hexenoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of 4-Hexenoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts 4-Hexenoyl-CoA into 4-Hexenoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, 4-Hexenoylcarnitine is converted back to 4-Hexenoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of 4-Hexenoyl-CoA occurs in four steps. First, since 4-Hexenoyl-CoA is a medium chain acyl-CoA it is the substrate for a medium chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of 4-Hexenoyl-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 k...