Classification Term: 169002
Acyl CoAs (ontology term: 78913d51825502483cf2158fc1f19903)
found 321 associated metabolites at sub_class metabolite taxonomy ontology rank level.
Ancestor: Fatty esters
Child Taxonomies: There is no child term of current ontology term.
Caffeoyl-CoA
C30H42N7O19P3S (929.1468972000001)
Caffeoyl-CoA is an acyl CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of caffeic acid. It is functionally related to a caffeic acid. It is a conjugate acid of a caffeoyl-CoA(4-). An acyl CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of caffeic acid.
Crotonoyl-CoA
Crotonoyl-CoA is an important component in several metabolic pathways, notably fatty acid and amino acid metabolism. It is the substrate of a group of enzymes acyl-Coenzyme A oxidases 1, 2, 3 (E.C.: 1.3.3.6) corresponding to palmitoyl, branched chain, and pristanoyl, respectively, in the peroxisomal fatty acid beta-oxidation, producing hydrogen peroxide. Abnormality of this group of enzymes is linked to coma, dehydration, diabetes, fatty liver, hyperinsulinemia, hyperlipidemia, and leukodystrophy. It is also a substrate of a group of enzymes called acyl-Coenzyme A dehydrogenase (E.C.:1.3.99-, including 1.3.99.2, 1.3.99.3) in the metabolism of fatty acids or branched chain amino acids in the mitochondria (Rozen et al., 1994). Acyl-Coenzyme A dehydrogenase (1.3.99.3) has shown to contribute to kidney-associated diseases, such as adrenogential syndrome, kidney failure, kidney tubular necrosis, homocystinuria, as well as other diseases including cretinism, encephalopathy, hypoglycemia, medium chain acyl-CoA dehydrogenase deficiency. The gene (ACADS) also plays a role in theta oscillation during sleep. In addition, crotonoyl-CoA is the substrate of enoyl coenzyme A hydratase (E.C.4.2.1.17) in the mitochondria during lysine degradation and tryptophan metabolism, benzoate degradation via CoA ligation; in contrast it is the product of this enzyme in the butanoate metabolism. Moreover, it is produced from multiple enzymes in the butanoate metabolism pathway, including 3-Hydroxybutyryl-CoA dehydratase (E.C.:4.2.1.55), glutaconyl-CoA decarboxylase (E.C.: 4.1.1.70), vinylacetyl-CoA Δ-isomerase (E.C.: 5.3.3.3), and trans-2-enoyl-CoA reductase (NAD+) (E.C.: 1.3.1.44). In lysine degradation and tryptophan metabolism, crotonoyl CoA is produced by glutaryl-Coenzyme A dehydrogenase (E.C.:1.3.99.7) lysine and tryptophan metabolic pathway. This enzyme is linked to type-1glutaric aciduria, metabolic diseases, movement disorders, myelinopathy, and nervous system diseases. [HMDB] Crotonoyl-CoA (CAS: 992-67-6) is an important component in several metabolic pathways, notably fatty acid and amino acid metabolism. It is the substrate of acyl-coenzyme A oxidases 1, 2, and 3 (EC 1.3.3.6) corresponding to palmitoyl, branched-chain, and pristanoyl, respectively. In peroxisomal fatty acid beta-oxidation, these enzymes produce hydrogen peroxide. Abnormalities in this group of enzymes are linked to coma, dehydration, diabetes, fatty liver, hyperinsulinemia, hyperlipidemia, and leukodystrophy. Crotonoyl-CoA is also a substrate of a group of enzymes called acyl-coenzyme A dehydrogenases (EC 1.3.99-, 1.3.99.2, 1.3.99.3) in the metabolism of fatty acids or branched-chain amino acids in the mitochondria (PMID: 7698750). Acyl-coenzyme A dehydrogenase has been shown to contribute to kidney-associated diseases, such as adrenogential syndrome, kidney failure, kidney tubular necrosis, homocystinuria, as well as other diseases including cretinism, encephalopathy, hypoglycemia, and medium-chain acyl-CoA dehydrogenase deficiency. The gene (ACADS) also plays a role in theta oscillation during sleep. In addition, crotonoyl-CoA is the substrate of enoyl-coenzyme A hydratase (EC 4.2.1.17) in the mitochondria during lysine degradation and tryptophan metabolism as well as benzoate degradation via CoA ligation. Crotonoyl-CoA is the product of this enzyme in butanoate metabolism. Moreover, it is produced from multiple enzymes in the butanoate metabolism pathway, including 3-hydroxybutyryl-CoA dehydratase (EC 4.2.1.55), glutaconyl-CoA decarboxylase (EC 4.1.1.70), vinylacetyl-CoA delta-isomerase (EC 5.3.3.3), and trans-2-enoyl-CoA reductase (NAD+) (EC 1.3.1.44). In lysine degradation and tryptophan metabolism, crotonoyl-CoA is produced by glutaryl-coenzyme A dehydrogenase (EC 1.3.99.7). This enzyme is linked to glutaric aciduria type I, metabolic diseases, movement disorders, myelinopathy, and nervous system diseases.
Malonyl-CoA
Malonyl-CoA belongs to the class of organic compounds known as acyl-CoAs. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, malonyl-CoA is considered to be a fatty ester lipid molecule. Malonyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, malonyl-CoA participates in a number of enzymatic reactions. In particular, malonyl-CoA can be biosynthesized from acetyl-CoA; which is mediated by the enzyme acetyl-CoA carboxylase 1. In addition, malonyl-CoA can be converted into malonic acid and coenzyme A; which is catalyzed by the enzyme fatty acid synthase. Outside of the human body, malonyl-CoA has been detected, but not quantified in, several different foods, such as rapes, mamey sapotes, jews ears, pepper (C. chinense), and Alaska wild rhubarbs. This could make malonyl-CoA a potential biomarker for the consumption of these foods. Malonyl-CoA is a coenzyme A derivative that plays a key role in fatty acid synthesis in the cytoplasmic and microsomal systems. Malonyl-coa, also known as malonyl coenzyme a or coenzyme a, s-(hydrogen propanedioate), is a member of the class of compounds known as acyl coas. Acyl coas are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, malonyl-coa is considered to be a fatty ester lipid molecule. Malonyl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Malonyl-coa can be found in a number of food items such as root vegetables, sourdock, ceylon cinnamon, and buffalo currant, which makes malonyl-coa a potential biomarker for the consumption of these food products. Malonyl-coa exists in E.coli (prokaryote) and yeast (eukaryote).
Methylmalonyl-CoA
Methylmalonyl-CoA is an intermediate in the metabolism of Propanoate. It is a substrate for Malonyl-CoA decarboxylase (mitochondrial), Methylmalonyl-CoA mutase (mitochondrial) and Methylmalonyl-CoA epimerase (mitochondrial). [HMDB] Methylmalonyl-CoA is an intermediate in the metabolism of Propanoate. It is a substrate for Malonyl-CoA decarboxylase (mitochondrial), Methylmalonyl-CoA mutase (mitochondrial) and Methylmalonyl-CoA epimerase (mitochondrial).
Octanoyl-CoA
C29H50N7O17P3S (893.2196640000001)
Octanoyl-CoA is a substrate for Trifunctional enzyme beta subunit (mitochondrial), Acyl-coenzyme A oxidase 1 (peroxisomal), 3-ketoacyl-CoA thiolase (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal), Nuclear receptor-binding factor 1, Acyl-CoA dehydrogenase (long-chain specific, mitochondrial), Acyl-coenzyme A oxidase 3 (peroxisomal), HPDHase, Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial), Acyl-coenzyme A oxidase 2 (peroxisomal) and Peroxisomal carnitine O-octanoyltransferase. [HMDB]. Octanoyl-CoA is found in many foods, some of which are millet, loganberry, horseradish, and sea-buckthornberry. Octanoyl-CoA is a substrate for Trifunctional enzyme beta subunit (mitochondrial), Acyl-coenzyme A oxidase 1 (peroxisomal), 3-ketoacyl-CoA thiolase (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal), Nuclear receptor-binding factor 1, Acyl-CoA dehydrogenase (long-chain specific, mitochondrial), Acyl-coenzyme A oxidase 3 (peroxisomal), HPDHase, Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial), Acyl-coenzyme A oxidase 2 (peroxisomal) and Peroxisomal carnitine O-octanoyltransferase.
Acetyl-CoA
C23H38N7O17P3S (809.1257688000001)
The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent. The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia)
Isobutyryl-CoA
C25H42N7O17P3S (837.1570672000001)
Isobutyryl-CoA is a substrate for Acyl-CoA dehydrogenase (short-chain specific, mitochondrial), Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial) and Acyl-CoA dehydrogenase (long-chain specific, mitochondrial). [HMDB] Isobutyryl-CoA is a substrate for Acyl-CoA dehydrogenase (short-chain specific, mitochondrial), Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial) and Acyl-CoA dehydrogenase (long-chain specific, mitochondrial). Acquisition and generation of the data is financially supported in part by CREST/JST.
Propionyl-CoA
Propionyl-CoA is an intermediate in the metabolism of propanoate. Propionic aciduria is caused by an autosomal recessive disorder of propionyl coenzyme A (CoA) carboxylase deficiency (EC 6.4.1.3). In propionic aciduria, propionyl CoA accumulates within the mitochondria in massive quantities; free carnitine is then esterified, creating propionyl carnitine, which is then excreted in the urine. Because the supply of carnitine in the diet and from synthesis is limited, such patients readily develop carnitine deficiency as a result of the increased loss of acylcarnitine derivatives. This condition demands supplementation of free carnitine above the normal dietary intake to continue to remove (detoxify) the accumulating organic acids. Propionyl-CoA is a substrate for Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial), Acetyl-coenzyme A synthetase 2-like (mitochondrial), Propionyl-CoA carboxylase alpha chain (mitochondrial), Methylmalonate-semialdehyde dehydrogenase (mitochondrial), Trifunctional enzyme beta subunit (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal), Acyl-CoA dehydrogenase (long-chain specific, mitochondrial), Malonyl-CoA decarboxylase (mitochondrial), Acetyl-coenzyme A synthetase (cytoplasmic), 3-ketoacyl-CoA thiolase (mitochondrial) and Propionyl-CoA carboxylase beta chain (mitochondrial). (PMID: 10650319) [HMDB] Propionyl-CoA is an intermediate in the metabolism of propanoate. Propionic aciduria is caused by an autosomal recessive disorder of propionyl coenzyme A (CoA) carboxylase deficiency (EC 6.4.1.3). In propionic aciduria, propionyl CoA accumulates within the mitochondria in massive quantities; free carnitine is then esterified, creating propionyl carnitine, which is then excreted in the urine. Because the supply of carnitine in the diet and from synthesis is limited, such patients readily develop carnitine deficiency as a result of the increased loss of acylcarnitine derivatives. This condition demands supplementation of free carnitine above the normal dietary intake to continue to remove (detoxify) the accumulating organic acids. Propionyl-CoA is a substrate for Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial), Acetyl-coenzyme A synthetase 2-like (mitochondrial), Propionyl-CoA carboxylase alpha chain (mitochondrial), Methylmalonate-semialdehyde dehydrogenase (mitochondrial), Trifunctional enzyme beta subunit (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal), Acyl-CoA dehydrogenase (long-chain specific, mitochondrial), Malonyl-CoA decarboxylase (mitochondrial), Acetyl-coenzyme A synthetase (cytoplasmic), 3-ketoacyl-CoA thiolase (mitochondrial) and Propionyl-CoA carboxylase beta chain (mitochondrial). (PMID: 10650319).
Glutaryl-CoA
C26H42N7O19P3S (881.1468972000001)
Glutaryl-CoA is a substrate for 2-oxoglutarate dehydrogenase E1 component (mitochondrial), Dihydrolipoyllysine-residue succinyltransferase component of 2- oxoglutarate dehydrogenase complex (mitochondrial) and Glutaryl-CoA dehydrogenase (mitochondrial). [HMDB] Glutaryl-CoA is a substrate for 2-oxoglutarate dehydrogenase E1 component (mitochondrial), Dihydrolipoyllysine-residue succinyltransferase component of 2- oxoglutarate dehydrogenase complex (mitochondrial) and Glutaryl-CoA dehydrogenase (mitochondrial).
OPC4-CoA
C35H56N7O18P3S (987.2615266000001)
OPC4-CoA participates in alpha-Linolenic acid metabolism. OPC4-CoA is converted from 3-Oxo-OPC6-CoA. However, OPC4-CoA reacts with acyl-CoA oxidase [EC:1.3.3.6] to produce trans-2-Enoyl-OPC4-CoA. [HMDB] OPC4-CoA participates in alpha-Linolenic acid metabolism. OPC4-CoA is converted from 3-Oxo-OPC6-CoA. However, OPC4-CoA reacts with acyl-CoA oxidase [EC:1.3.3.6] to produce trans-2-Enoyl-OPC4-CoA.
trans-2-Enoyl-OPC6-CoA
trans-2-Enoyl-OPC6-CoA participates in alpha-linolenic acid metabolism. trans-2-Enoyl-OPC6-CoA is converted from OPC6-CoA via acyl-CoA oxidase [EC:1.3.3.6]. α-linolenic acid is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is an isomer of γ-linolenic acid, a polyunsaturated n−6 (omega-6) fatty acid. [HMDB] trans-2-Enoyl-OPC6-CoA participates in alpha-linolenic acid metabolism. trans-2-Enoyl-OPC6-CoA is converted from OPC6-CoA via acyl-CoA oxidase [EC:1.3.3.6]. α-linolenic acid is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is an isomer of γ-linolenic acid, a polyunsaturated n−6 (omega-6) fatty acid.
trans-2-Enoyl-OPC8-CoA
C39H62N7O18P3S (1041.3084741999999)
trans-2-Enoyl-OPC8-CoA participates in alpha-linolenic acid metabolism. trans-2-Enoyl-OPC8-CoA is converted from OPC8-CoA via acyl-CoA oxidase [EC:1.3.3.6]. α-linolenic acid is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is an isomer of γ-linolenic acid, a polyunsaturated n−6 (omega-6) fatty acid. [HMDB] trans-2-Enoyl-OPC8-CoA participates in alpha-linolenic acid metabolism. trans-2-Enoyl-OPC8-CoA is converted from OPC8-CoA via acyl-CoA oxidase [EC:1.3.3.6]. α-linolenic acid is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is an isomer of γ-linolenic acid, a polyunsaturated n−6 (omega-6) fatty acid.
Succinyl-CoA
Succinyl-CoA is an important intermediate in the citric acid cycle, where it is synthesized from α-Ketoglutarate by α-ketoglutarate dehydrogenase (EC 1.2.4.2) through decarboxylation, and is converted into succinate through the hydrolytic release of coenzyme A by succinyl-CoA synthetase (EC 6.2.1.5). Succinyl-CoA may be an end product of peroxisomal beta-oxidation of dicarboxylic fatty acids; the identification of an apparently specific succinyl-CoA thioesterase (ACOT4, EC 3.1.2.3, hydrolyzes succinyl-CoA) in peroxisomes strongly suggests that succinyl-CoA is formed in peroxisomes. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A, thereby regulating levels of these compounds. (PMID: 16141203) [HMDB]. Succinyl-CoA is found in many foods, some of which are fruits, sea-buckthornberry, pomegranate, and sweet orange. Succinyl-CoA is an important intermediate in the citric acid cycle, where it is synthesized from α-Ketoglutarate by α-ketoglutarate dehydrogenase (EC 1.2.4.2) through decarboxylation, and is converted into succinate through the hydrolytic release of coenzyme A by succinyl-CoA synthetase (EC 6.2.1.5). Succinyl-CoA may be an end product of peroxisomal beta-oxidation of dicarboxylic fatty acids; the identification of an apparently specific succinyl-CoA thioesterase (ACOT4, EC 3.1.2.3, hydrolyzes succinyl-CoA) in peroxisomes strongly suggests that succinyl-CoA is formed in peroxisomes. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A, thereby regulating levels of these compounds. (PMID: 16141203).
Acetoacetyl-CoA
Acetoacetyl-CoA is an intermediate in the metabolism of Butanoate. It is a substrate for Succinyl-CoA:3-ketoacid-coenzyme A transferase 1 (mitochondrial), Hydroxymethylglutaryl-CoA synthase (mitochondrial), Short chain 3-hydroxyacyl-CoA dehydrogenase (mitochondrial), Trifunctional enzyme beta subunit (mitochondrial), Hydroxymethylglutaryl-CoA synthase (cytoplasmic), Peroxisomal bifunctional enzyme, Acetyl-CoA acetyltransferase (cytosolic), Acetyl-CoA acetyltransferase (mitochondrial), 3-hydroxyacyl-CoA dehydrogenase type II, Succinyl-CoA:3-ketoacid-coenzyme A transferase 2 (mitochondrial), 3-ketoacyl-CoA thiolase (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal) and Trifunctional enzyme alpha subunit (mitochondrial). [HMDB]. Acetoacetyl-CoA is found in many foods, some of which are bog bilberry, lemon balm, pineapple, and pak choy. Acetoacetyl-CoA belongs to the class of organic compounds known as aminopiperidines. Aminopiperidines are compounds containing a piperidine that carries an amino group. Acetoacetyl-CoA is a strong basic compound (based on its pKa). In humans, acetoacetyl-CoA is involved in the metabolic disorder called the short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (HADH) pathway. Acetoacetyl-CoA is an intermediate in the metabolism of butanoate. It is a substrate for succinyl-CoA:3-ketoacid-coenzyme A transferase, hydroxymethylglutaryl-CoA synthase, short-chain 3-hydroxyacyl-CoA dehydrogenase, peroxisomal bifunctional enzyme, acetyl-CoA acetyltransferase, and 3-ketoacyl-CoA thiolase.
3-Hydroxy-3-methylglutaryl-CoA
3-Hydroxy-3-methylglutaryl-CoA (HMG-CoA) (CAS: 1553-55-5) is formed when acetyl-CoA condenses with acetoacetyl-CoA in a reaction that is catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway or mevalonate-dependent (MAD) route, an important cellular metabolic pathway present in virtually all organisms. HMG-CoA reductase (EC 1.1.1.34) inhibitors, more commonly known as statins, are cholesterol-lowering drugs that have been widely used for many years to reduce the incidence of adverse cardiovascular events. HMG-CoA reductase catalyzes the rate-limiting step in the mevalonate pathway and these agents lower cholesterol by inhibiting its synthesis in the liver and in peripheral tissues. Androgen also stimulates lipogenesis in human prostate cancer cells directly by increasing transcription of the fatty acid synthase and HMG-CoA-reductase genes (PMID: 14689582). (s)-3-hydroxy-3-methylglutaryl-coa, also known as hmg-coa or hydroxymethylglutaroyl coenzyme a, is a member of the class of compounds known as (s)-3-hydroxy-3-alkylglutaryl coas (s)-3-hydroxy-3-alkylglutaryl coas are 3-hydroxy-3-alkylglutaryl-CoAs where the 3-hydroxy-3-alkylglutaryl component has (S)-configuration. Thus, (s)-3-hydroxy-3-methylglutaryl-coa is considered to be a fatty ester lipid molecule (s)-3-hydroxy-3-methylglutaryl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). (s)-3-hydroxy-3-methylglutaryl-coa can be found in a number of food items such as watercress, burdock, spirulina, and chicory, which makes (s)-3-hydroxy-3-methylglutaryl-coa a potential biomarker for the consumption of these food products (s)-3-hydroxy-3-methylglutaryl-coa may be a unique S.cerevisiae (yeast) metabolite.
Stearoyl-CoA
Stearoyl-CoA is a long-chain acyl CoA ester that acts as an intermediate metabolite in the biosynthesis of monounsaturated fatty acids; a critical committed step in the reaction is the introduction of the cis-configuration double bond into acyl-CoAs (between carbons 9 and 10). This oxidative reaction is catalyzed by the iron-containing, microsomal enzyme, stearoyl-CoA desaturase (SCD, EC 1.14.19.1). NADH supplies the reducing equivalents for the reaction, the flavoprotein is cytochrome b5-reductase and the electron carrier is the heme protein cytochrome b5. Stearoyl-CoA is converted into oleoyl-CoA and then used as a major substrate for the synthesis of various kinds of lipids including phospholipids, triglycerides, cholesteryl esters and wax esters. Oleic acid is the preferred substrate for acyl-CoA cholesterol acyltransferase (ACAT, EC 2.3.1.26) and diacylglycerol acyltransferase (DGAT, EC 2.3.1.20), the enzymes responsible for cholesteryl esters and triglycerides synthesis, respectively. In addition oleate is the major monounsaturated fatty acid in human adipose tissue and in the phospholipid of the red-blood-cell membrane. In the biosynthesis of sphinganine, stearoyl-CoA proceeds through the acyl-CoA + serine -> 3-keto-sphinganine -> sphinganine pathway, with the key enzyme being acyl-CoA serine acyltransferase (EC 2.3.1.50) to yield C20-(3-ketosphinganine) long-chain base. There is growing recognition that acyl-CoA esters could act as signaling molecules in cellular metabolism. (PMID: 12538075, 10998569, Prostaglandins Leukot Essent Fatty Acids. 2003 Feb;68(2):113-21.) [HMDB]. Stearoyl-CoA is found in many foods, some of which are romaine lettuce, grapefruit/pummelo hybrid, radish, and european cranberry. Stearoyl-CoA is a long-chain acyl CoA ester that acts as an intermediate metabolite in the biosynthesis of monounsaturated fatty acids; a critical committed step in the reaction is the introduction of the cis-configuration double bond into acyl-CoAs (between carbons 9 and 10). This oxidative reaction is catalyzed by the iron-containing, microsomal enzyme, stearoyl-CoA desaturase (SCD, EC 1.14.19.1). NADH supplies the reducing equivalents for the reaction, the flavoprotein is cytochrome b5-reductase and the electron carrier is the heme protein cytochrome b5. Stearoyl-CoA is converted into oleoyl-CoA and then used as a major substrate for the synthesis of various kinds of lipids including phospholipids, triglycerides, cholesteryl esters and wax esters. Oleic acid is the preferred substrate for acyl-CoA cholesterol acyltransferase (ACAT, EC 2.3.1.26) and diacylglycerol acyltransferase (DGAT, EC 2.3.1.20), the enzymes responsible for cholesteryl esters and triglycerides synthesis, respectively. In addition oleate is the major monounsaturated fatty acid in human adipose tissue and in the phospholipid of the red-blood-cell membrane. In the biosynthesis of sphinganine, stearoyl-CoA proceeds through the acyl-CoA + serine -> 3-keto-sphinganine -> sphinganine pathway, with the key enzyme being acyl-CoA serine acyltransferase (EC 2.3.1.50) to yield C20-(3-ketosphinganine) long-chain base. There is growing recognition that acyl-CoA esters could act as signaling molecules in cellular metabolism. (PMID: 12538075, 10998569, Prostaglandins Leukot Essent Fatty Acids. 2003 Feb;68(2):113-21.).
Oleoyl-CoA
Oleoyl-CoA is a substrate for Acyl-CoA desaturase and Protein FAM34A. [HMDB]. Oleoyl-CoA is found in many foods, some of which are cardoon, fruits, hyssop, and rice. Oleoyl-CoA is a substrate for Acyl-CoA desaturase and Protein FAM34A.
Itaconyl-CoA
Itaconyl-CoA is an intermediate metabolite in the degradation pathway of itaconic acid, an unsaturated dicarbonic organic acid. Citramalyl coenzyme A (CoA) is found to be the intermediate in the conversion of itaconyl-Co-A to acetyl-CoA and pyruvate, catalyzed by methylglutaconase. Methylglutaconase catalyzes the interconversion of itaconyl-, mesaconyl-, and citramalyl-CoA. In liver mitochondria, methylglutaconase converts itaconate to pyruvate and acetyl coenzyme A. In this metabolic process, itaconate is first activated to itaconyl-CoA by a succinate activating enzyme, and a CoA derivative is cleaved to acetyl-CoA and pyruvate. (PMID: 13783048, 11548996) [HMDB]. Itaconyl-CoA is found in many foods, some of which are red algae, barley, garden rhubarb, and chestnut. Itaconyl-CoA is an intermediate metabolite in the degradation pathway of itaconic acid, an unsaturated dicarbonic organic acid. Citramalyl coenzyme A (CoA) is found to be the intermediate in the conversion of itaconyl-Co-A to acetyl-CoA and pyruvate, catalyzed by methylglutaconase. Methylglutaconase catalyzes the interconversion of itaconyl-, mesaconyl-, and citramalyl-CoA. In liver mitochondria, methylglutaconase converts itaconate to pyruvate and acetyl coenzyme A. In this metabolic process, itaconate is first activated to itaconyl-CoA by a succinate activating enzyme, and a CoA derivative is cleaved to acetyl-CoA and pyruvate. (PMID: 13783048, 11548996).
Cinnamoyl-CoA
C30H42N7O17P3S (897.1570672000001)
Cinnamoyl-coa is a member of the class of compounds known as 2-enoyl coas. 2-enoyl coas are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain. Cinnamoyl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Cinnamoyl-coa can be found in sorghum, which makes cinnamoyl-coa a potential biomarker for the consumption of this food product. Cinnamoyl-Coenzyme A is an intermediate in the phenylpropanoids metabolic pathway .
Phenylacetyl-CoA
C29H42N7O17P3S (885.1570672000001)
Phenylacetyl-CoA was found to be a very potent inhibitor of choline acetyltransferase, competitive for acetyl-CoA with Ki of 3.1 X 10(-7)M. Phenylacetate exerts its neurotoxic action through its metabolic product, phenylacetyl-CoA, which could severely decrease the availability of acetyl-CoA. (PMID: 6142928) [HMDB] Phenylacetyl-CoA was found to be a very potent inhibitor of choline acetyltransferase, competitive for acetyl-CoA with Ki of 3.1 X 10(-7)M. Phenylacetate exerts its neurotoxic action through its metabolic product, phenylacetyl-CoA, which could severely decrease the availability of acetyl-CoA (PMID: 6142928).
Lactyl-CoA
Lactyl-CoA is involved in both propanoate metabolism and styrene degradation pathways. It is a product in styrene degradation pathway. (KEGG) [HMDB] Lactyl-CoA is involved in both propanoate metabolism and styrene degradation pathways. It is a product in styrene degradation pathway. (KEGG).
Pentanoyl-CoA
Pentanoyl CoA is an acyl-CoA with the C-5 Acyl chain. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine. Pentanoyl coA is a acyl-CoA with the C-5 Acyl chain.
Citramalyl-CoA
C26H42N7O20P3S (897.1418122000001)
An acyl-CoA having citramalyl as the S-acyl group.
pimeloyl-CoA
C28H46N7O19P3S (909.1781956000001)
Pimeloyl-coa, also known as pimeloyl-coenzyme a or 6-carboxyhexanoyl-coa, is a member of the class of compounds known as 2,3,4-saturated fatty acyl coas. 2,3,4-saturated fatty acyl coas are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain. Thus, pimeloyl-coa is considered to be a fatty ester lipid molecule. Pimeloyl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Pimeloyl-coa can be synthesized from pimelic acid and coenzyme A. Pimeloyl-coa is also a parent compound for other transformation products, including but not limited to, 3-hydroxypimeloyl-CoA, 3-oxopimeloyl-CoA, and 2,3-didehydropimeloyl-CoA. Pimeloyl-coa can be found in a number of food items such as german camomile, rose hip, chinese chestnut, and star anise, which makes pimeloyl-coa a potential biomarker for the consumption of these food products. Pimeloyl-coa may be a unique S.cerevisiae (yeast) metabolite.
Choloyl-CoA
C45H74N7O20P3S (1157.3921994000002)
Choloyl-CoA is an intermediate metabolite in the Bile acid biosynthesis (KEGG). The conjugation of bile acids to glycine and taurine for excretion into bile occurs via a reaction catalyzed by the enzyme Bile acid-CoA:amino acid N-acyltransferase (BACAT) catalyzes. Choloyl-CoA is an intermediate metabolite in the Bile acid biosynthesis (KEGG) D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts D005765 - Gastrointestinal Agents > D002793 - Cholic Acids
Lauroyl-CoA
Lauroyl-CoA is a substrate for Protein FAM34A. [HMDB]. Lauroyl-CoA is found in many foods, some of which are apricot, hazelnut, other soy product, and thistle. Lauroyl-CoA is a substrate for Protein FAM34A.
Biotinyl-CoA
An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of biotin.
Nonanoyl-CoA
C30H52N7O17P3S (907.2353132000001)
Nonanoyl CoA is an acyl-CoA with the C-9 fatty acid Acyl chain moiety. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine. Nonanoyl coA is a acyl-CoA with the C-9 fatty acid Acyl chain moiety.
Farnesoyl-CoA
A multi-methyl-branched fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of farnesoic acid.
Eicosanoyl-CoA
Eicosanoyl-CoA is an intermediate metabolite in the synthesis of phosphatidic acid, a substrate of lysophosphatidic acid acyltransferase with high specificity as an acyl donor. Cells and membranes of mammalian cells synthesize their glycerophospholipids and triglycerides to maintain the cellular integrity and to provide energy for cellular functions. The phospholipids are synthesized de novo in cells through an evolutionary conserved process involving serial acylations of glycerol-3-phosphate. Several isoforms of the enzyme 1-acylglycerol-3-phosphate-O-acyltransferase (EC 2.3.1.51, AGPAT) acylate lysophosphatidic acid at the sn-2 position to produce phosphatidic acid. Bile acid-CoA:amino acid N-acyltransferase (EC 2.3.1.65, BACAT) catalyzes the conjugation of bile acids to glycine and taurine for excretion into bile and can utilize Eicosanoyl-CoA as an acyl donor as well; this may play important roles in protection against toxicity by accumulation of unconjugated bile acids and non-esterified very long-chain fatty acids. (PMID: 17535882, 12810727) [HMDB] Eicosanoyl-CoA is an intermediate metabolite in the synthesis of phosphatidic acid, a substrate of lysophosphatidic acid acyltransferase with high specificity as an acyl donor. Cells and membranes of mammalian cells synthesize their glycerophospholipids and triglycerides to maintain the cellular integrity and to provide energy for cellular functions. The phospholipids are synthesized de novo in cells through an evolutionary conserved process involving serial acylations of glycerol-3-phosphate. Several isoforms of the enzyme 1-acylglycerol-3-phosphate-O-acyltransferase (EC 2.3.1.51, AGPAT) acylate lysophosphatidic acid at the sn-2 position to produce phosphatidic acid. Bile acid-CoA:amino acid N-acyltransferase (EC 2.3.1.65, BACAT) catalyzes the conjugation of bile acids to glycine and taurine for excretion into bile and can utilize Eicosanoyl-CoA as an acyl donor as well; this may play important roles in protection against toxicity by accumulation of unconjugated bile acids and non-esterified very long-chain fatty acids. (PMID: 17535882, 12810727).
Linoleoyl-CoA
Linoleoyl-CoA is the acyl-CoA of linoleic acid found in the human body. It binds to and results in decreased activity of glutathione S-transferase1. It has been proposed that inhibition of mitochondrial adenine nucleotide translocator by long-chain acyl-CoA underlies the mechanism associating obesity and type 2 diabetes. Unsaturated fatty acids play an important role in the prevention of human diseases such as diabetes, obesity, cancer, and neurodegeneration. Their oxidation in vivo by acyl-CoA dehydrogenases (ACADs) catalyze the first step of each cycle of mitochondrial fatty acid beta-oxidation. ACAD-9 had maximal activity with long-chain unsaturated acyl-CoAs as substrates (PMID: 17184976, 16020546).
Phytanoyl-CoA
Phytanoyl CoA is a coenzyme A derivative of phytanic acid. Phytanic acid is present in human diet or in animal tissues where it may be derived from chlorophyll in plant extracts. Specifically it is an epimeric metabolite of the isoprenoid side chain of chlorophyll. Owing to the presence of its epimeric beta-methyl group, phytanic acid cannot be metabolized by beta-oxidation. Instead, it is metabolized in peroxisomes via alpha-oxidation to give pristanic acid, which is then oxidized by beta-oxidation. PhyH (phytanoyl-CoA 2-hydroxylase) catalyses hydroxylation of phytanoyl-CoA. Mutations of PhyH can lead to phytanic acid accumulation. High levels of phytanic acid are found in patients suffering from Refsums syndrome. This inherited neurological disorder is characterized by an accumulation of phytanic acid in blood and tissues. Clinically it is characterized by adult onset retinitis pigmentosa, anosmia, sensory neuropathy, and phytanic acidaemia. This disorder has been found to be related to deficiency in the α-oxidation pathway in the liver. (PMID: 17956235). Phytanoyl CoA and other branched-chain fatty acid CoA products are potent inducers of the peroxisome proliferator-activated receptor PPARalpha, a nuclear receptor that enhances transcription of peroxisomal enzymes mediating beta-oxidation of these potentially toxic fatty acids (PMID: 16768463). Pyruvate dehydrogenase and 2-oxoglutarate dehydrogenase are strongly inhibited by phytanoyl-CoA. Decreased activity of these important mitochondrial metabolism complexes might therefore contribute to neurological symptoms upon accumulation of phytanic acid in Refsum disease (PMID: 16737698). [HMDB] Phytanoyl CoA is a coenzyme A derivative of phytanic acid. Phytanic acid is present in human diet or in animal tissues where it may be derived from chlorophyll in plant extracts. Specifically it is an epimeric metabolite of the isoprenoid side chain of chlorophyll. Owing to the presence of its epimeric beta-methyl group, phytanic acid cannot be metabolized by beta-oxidation. Instead, it is metabolized in peroxisomes via alpha-oxidation to give pristanic acid, which is then oxidized by beta-oxidation. PhyH (phytanoyl-CoA 2-hydroxylase) catalyses hydroxylation of phytanoyl-CoA. Mutations of PhyH can lead to phytanic acid accumulation. High levels of phytanic acid are found in patients suffering from Refsums syndrome. This inherited neurological disorder is characterized by an accumulation of phytanic acid in blood and tissues. Clinically it is characterized by adult onset retinitis pigmentosa, anosmia, sensory neuropathy, and phytanic acidaemia. This disorder has been found to be related to deficiency in the α-oxidation pathway in the liver. (PMID: 17956235). Phytanoyl CoA and other branched-chain fatty acid CoA products are potent inducers of the peroxisome proliferator-activated receptor PPARalpha, a nuclear receptor that enhances transcription of peroxisomal enzymes mediating beta-oxidation of these potentially toxic fatty acids (PMID: 16768463). Pyruvate dehydrogenase and 2-oxoglutarate dehydrogenase are strongly inhibited by phytanoyl-CoA. Decreased activity of these important mitochondrial metabolism complexes might therefore contribute to neurological symptoms upon accumulation of phytanic acid in Refsum disease (PMID: 16737698).
3-Oxoadipyl-CoA
C27H42N7O20P3S (909.1418122000001)
This compound belongs to the family of 3-Oxo-acyl CoAs. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
Arachidonyl-CoA
Arachidonyl-CoA is an intermediate in Biosynthesis of unsaturated fatty acids. Arachidonyl-CoA is produced from 8,11,14-Eicosatrienoyl-CoA via the enzyme fatty acid desaturase 1 (EC 1.14.19.-). It is then converted to Arachidonic acid via the enzymepalmitoyl-CoA hydrolase (EC 3.1.2.2).
Beta-Alanyl-CoA
C24H41N8O17P3S (838.1523166000001)
beta-Alanyl-CoA is involved in the beta-alanine and propanoate metabolism systems. beta-Alanyl-CoA is reversibly produced from acrylyl-CoA by enzyme β-alanyl-CoA ammonia-lyase [4.3.1.6]. [HMDB] beta-Alanyl-CoA is involved in the beta-alanine and propanoate metabolism systems. beta-Alanyl-CoA is reversibly produced from acrylyl-CoA by enzyme β-alanyl-CoA ammonia-lyase [4.3.1.6].
Glutaconyl-CoA
Glutaconyl-CoA (CAS: 6712-05-6), also known as 4-carboxybut-2-enoyl-CoA, belongs to the class of organic compounds known as 2-enoyl CoAs. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain. Thus, glutaconyl-CoA is considered to be a fatty ester lipid molecule. Glutaconyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Glutaconyl-CoA is a substrate for glutaryl-CoA dehydrogenase. Glutaconyl-CoA is a substrate for Glutaryl-CoA dehydrogenase (mitochondrial). [HMDB]
Isovaleryl-CoA
Isovaleryl-CoA is an intermediate metabolite in the catabolic pathway of leucine. The accumulation of derivatives of isovaleryl-CoA occurs in patients affected with isovaleric acidemia (IVA, OMIM 243500) an autosomal recessive inborn error of leucine metabolism caused by a deficiency of the mitochondrial enzyme isovaleryl-CoA dehydrogenase (IVD, EC 1.3.99.10, a flavoenzyme that catalyzes the conversion of isovaleryl-CoA to 3-methylcrotonyl-CoA). IVA was the first organic acidemia recognized in humans and can cause significant morbidity and mortality. Early diagnosis and treatment with a protein restricted diet and supplementation with carnitine and glycine are effective in promoting normal development in severely affected individuals. Both intra- and interfamilial variability have been recognized. Initially, two phenotypes with either an acute neonatal or a chronic intermittent presentation were described. More recently, a third group of individuals with mild biochemical abnormalities who can be asymptomatic have been identified through newborn screening of blood spots by tandem mass spectrometry. The majority of patients with IVA today are diagnosed pre-symptomatically through newborn screening by use of MS/MS which reveals elevations of the marker metabolite C5 acylcarnitine in dried blood spots. C5 acylcarnitine represents a mixture of isomers (isovalerylcarnitine, 2-methylbutyrylcarnitine, and pivaloylcarnitine). (PMID: 16602101, Am J Med Genet C Semin Med Genet. 2006 May 15;142(2):95-103.) [HMDB]. Isovaleryl-CoA is found in many foods, some of which are purple laver, alaska wild rhubarb, macadamia nut (m. tetraphylla), and green zucchini. Isovaleryl-CoA is an intermediate metabolite in the catabolic pathway of leucine. The accumulation of derivatives of isovaleryl-CoA occurs in patients affected with isovaleric acidemia (IVA, OMIM: 243500), an autosomal recessive inborn error of leucine metabolism caused by a deficiency of the mitochondrial enzyme isovaleryl-CoA dehydrogenase (IVD, EC 1.3.99.10), a flavoenzyme that catalyzes the conversion of isovaleryl-CoA into 3-methylcrotonyl-CoA. IVA was the first organic acidemia recognized in humans and can cause significant morbidity and mortality. Early diagnosis and treatment with a protein-restricted diet and supplementation with carnitine and glycine are effective in promoting normal development in severely affected individuals. Both intra- and interfamilial variability have been recognized. Initially, two phenotypes with either an acute neonatal or a chronic intermittent presentation were described. More recently, a third group of individuals with mild biochemical abnormalities who can be asymptomatic have been identified through newborn screening of blood spots by tandem mass spectrometry. The majority of patients with IVA today are diagnosed pre-symptomatically through newborn screening by use of MS/MS which reveals elevations of the marker metabolite C5 acylcarnitine in dried blood spots. C5 Acylcarnitine represents a mixture of isomers (isovalerylcarnitine, 2-methylbutyrylcarnitine, and pivaloylcarnitine) (PMID: 16602101).
3Z-dodecenoyl-CoA
C33H56N7O17P3S (947.2666116000001)
3Z-dodecenoyl-CoA is an intermediate in fatty acid metabolism. 3Z-dodecenoyl-CoA is converted from trans-Dodec-2-enoyl-CoA via acyl-CoA oxidase, acyl-CoA dehydrogenase, and long-chain-acyl-CoA dehydrogenase [EC:1.3.3.6, 1.3.99.3, 1.3.99.13] [HMDB] 3Z-dodecenoyl-CoA is an intermediate in fatty acid metabolism. 3Z-dodecenoyl-CoA is converted from trans-Dodec-2-enoyl-CoA via acyl-CoA oxidase, acyl-CoA dehydrogenase, and long-chain-acyl-CoA dehydrogenase [EC:1.3.3.6, 1.3.99.3, 1.3.99.13].
Gamma-linolenoyl-CoA
Gamma-linolenoyl-CoA is the product of a chemical reaction that involves linoleoyl-CoA desaturase which acts as a catalyst. In enzymology, linoleoyl-CoA desaturase (EC 1.14.19.3) is an enzyme that catalyzes the chemical reaction. linoleoyl-CoA + AH2 + O2 gamma-linolenoyl-CoA + A + 2 H2O. The 3 substrates of this enzyme are linoleoyl-CoA, AH2, and O2, whereas its 3 products are gamma-linolenoyl-CoA, A, and H2O. (Wikipedia). gamma-Linolenoyl-CoA is the product of a chemical reaction that involves linoleoyl-CoA desaturase which acts as a catalyst. In enzymology, linoleoyl-CoA desaturase (EC 1.14.19.3) is an enzyme that catalyzes the chemical reaction
2-Hydroxyglutaryl-CoA
C26H42N7O20P3S (897.1418122000001)
A hydroxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 2-hydroxyglutaric acid.
3-Methylglutaconyl-CoA
C27H42N7O19P3S (893.1468972000001)
3-Methylglutaconyl-CoA is a substrate for Methylglutaconyl-CoA hydratase (mitochondrial), Methylcrotonoyl-CoA carboxylase beta chain (mitochondrial) and Methylcrotonoyl-CoA carboxylase alpha chain (mitochondrial). [HMDB]. 3-Methylglutaconyl-CoA is found in many foods, some of which are cocoa bean, evening primrose, winter squash, and rocket salad (sspecies). 3-Methylglutaconyl-CoA is a substrate for Methylglutaconyl-CoA hydratase (mitochondrial), Methylcrotonoyl-CoA carboxylase beta chain (mitochondrial) and Methylcrotonoyl-CoA carboxylase alpha chain (mitochondrial). COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
5-hydroxypentanoyl-CoA
An acyl-CoA resulting from the formal condensation of the thiol group of coenzyme A with the carboxylic acid group of 5-hydroxypentanoic acid.
2-Methylacetoacetyl-CoA
C26H42N7O18P3S (865.1519822000001)
2-Methylacetoacetyl-CoA belongs to the class of organic compounds known as 3-oxo-acyl CoAs. These are organic compounds containing a 3-oxo acylated coenzyme A derivative. 2-Methylacetoacetyl-CoA is a substrate for 3-hydroxyacyl-CoA dehydrogenase type II, 3-ketoacyl-CoA thiolase (mitochondrial), peroxisomal bifunctional enzyme, trifunctional enzyme beta subunit (mitochondrial), short chain 3-hydroxyacyl-CoA dehydrogenase (mitochondrial), and 3-ketoacyl-CoA thiolase (peroxisomal). 2-Methylacetoacetyl-CoA is a substrate for 3-hydroxyacyl-CoA dehydrogenase type II, 3-ketoacyl-CoA thiolase (mitochondrial), Peroxisomal bifunctional enzyme, Trifunctional enzyme beta subunit (mitochondrial), Short chain 3-hydroxyacyl-CoA dehydrogenase (mitochondrial) and 3-ketoacyl-CoA thiolase (peroxisomal). [HMDB]. 2-Methylacetoacetyl-CoA is found in many foods, some of which are spirulina, macadamia nut (m. tetraphylla), root vegetables, and yardlong bean.
Methacrylyl-CoA
Methacrylyl-CoA, also known as methacryloyl-CoA, belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O. Thus, methacrylyl-CoA is considered to be a fatty ester lipid molecule. Methacrylyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Methacrylyl-CoA has been detected, but not quantified in, several different foods, such as beechnuts, hyacinth beans, devilfish, eggplants, and cupuaçus. This could make methacrylyl-CoA a potential biomarker for the consumption of these foods. Methacrylyl-CoA is a metabolite in the valine, leucine, and isoleucine degradation pathway and highly reacts with free thiol compounds (PMID: 14684172). Cirrhosis results in a significant decrease in 3-hydroxyisobutyryl-CoA hydrolase activity, a key enzyme in the valine catabolic pathway that plays an important role in the catabolism of a potentially toxic compound, methacrylyl-CoA, formed as an intermediate in the catabolism of valine and isobutyrate (PMID: 8938168). Methacrylyl-coenzyme a, also known as methylacrylyl-coa or 2-methylprop-2-enoyl-coa, is a member of the class of compounds known as acyl coas. Acyl coas are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, methacrylyl-coenzyme a is considered to be a fatty ester lipid molecule. Methacrylyl-coenzyme a is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Methacrylyl-coenzyme a can be found in a number of food items such as tea leaf willow, mexican groundcherry, new zealand spinach, and parsnip, which makes methacrylyl-coenzyme a a potential biomarker for the consumption of these food products.
7-methyl-3-oxooctanoyl-CoA
C30H50N7O18P3S (921.2145790000001)
An oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxylic acid group of 7-methyl-3-oxooctanoic acid.
Malyl-CoA
Malyl-CoA is a substrate of enzyme malyl-CoA lyase [EC 4.1.3.24] in glyoxylate and dicarboxylate metabolism pathway (KEGG). [HMDB] Malyl-CoA is a substrate of enzyme malyl-CoA lyase [EC 4.1.3.24] in glyoxylate and dicarboxylate metabolism pathway (KEGG).
2-Methyl-3-hydroxybutyryl-CoA
2-Methyl-3-hydroxybutyryl-CoA (CAS: 6701-38-8) belongs to the class of organic compounds known as (S)-3-hydroxyacyl-CoAs. These are organic compounds containing an (S)-3-hydroxyl acylated coenzyme A derivative. Thus, 2-methyl-3-hydroxybutyryl-CoA is considered to be a fatty ester lipid molecule. 2-Methyl-3-hydroxybutyryl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Methyl-3-hydroxybutyryl-CoA is a substrate for 3-hydroxyacyl-CoA dehydrogenase type II, enoyl-CoA hydratase, trifunctional enzyme alpha subunit, short-chain 3-hydroxyacyl-CoA dehydrogenase, and peroxisomal bifunctional enzyme. 2-Methyl-3-hydroxybutyryl-CoA is a substrate for 3-hydroxyacyl-CoA dehydrogenase type II, Enoyl-CoA hydratase (mitochondrial), Trifunctional enzyme alpha subunit (mitochondrial), Short chain 3-hydroxyacyl-CoA dehydrogenase (mitochondrial) and Peroxisomal bifunctional enzyme. [HMDB]. 2-Methyl-3-hydroxybutyryl-CoA is found in many foods, some of which are malus (crab apple), sweet potato, white cabbage, and agave.
3-Oxotetradecanoyl-CoA
C35H60N7O18P3S (991.2928250000001)
3-Oxotetradecanoyl-CoA is a product of the peroxisomal beta oxidation of hexadenoic acid by the enzyme acyl-CoA oxidase which results in long-chain 3-oxoacyl-CoA-esters. (PMID: 7548202). Myristoyl-CoA:protein N-myristoyltransferase (E.C. 2.3.1.97) is a eukaryotic enzyme that catalyzes the transfer of myristate (C14:O) from myristoyl-CoA to the amino nitrogen of glycine. This covalent protein modification occurs cotranslationally, is apparently irreversible, and affects proteins with diverse functions. (PMID: 2818568). 3-Oxotetradecanoyl-CoA is a product of the peroxisomal beta oxidation of hexadenoic acid by the enzyme acyl-CoA oxidase which results in long-chain 3-oxoacyl-CoA-esters. (PMID: 7548202)
3-Oxodecanoyl-CoA
C31H52N7O18P3S (935.2302281999999)
3-oxodecanoyl-coa, also known as 3-ketodecanoyl-CoA is an acyl-CoA or acyl-coenzyme A. More specifically, it is a 3-oxodecanoic acid thioester of coenzyme A. 3-oxodecanoyl-coa is an acyl-CoA with 10 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. 3-oxodecanoyl-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. 3-oxodecanoyl-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, 3-Oxodecanoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of 3-Oxodecanoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts 3-Oxodecanoyl-CoA into 3-oxodecanoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, 3-oxodecanoylcarnitine is converted back to 3-Oxodecanoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of 3-Oxodecanoyl-CoA occurs in four steps. First, since 3-Oxodecanoyl-CoA is a medium chain acyl-CoA it is the substrate for a medium chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of 3-Oxodecanoyl-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 ... 3-Oxodecanoyl-CoA is an intermediate in fatty acid metabolism, the substrate of the enzyme acetyl-Coenzyme A acetyltransferase 1 and 2 [EC:2.3.1.16-2.3.1.9]; 3-Oxodecanoyl-CoA is an intermediate in fatty acid elongation in mitochondria, being the substrate of the enzymes beta-hydroxyacyl-CoA dehydrogenase and 3-hydroxyacyl-CoA dehydrogenase [EC 1.1.1.211-1.1.1.35]. (KEGG) [HMDB]. 3-Oxodecanoyl-CoA is found in many foods, some of which are chinese cabbage, calabash, safflower, and sunburst squash (pattypan squash).
3-Oxooctanoyl-CoA
3-Oxooctanoyl-CoA is the substrate of the acetyl-CoA C-acyltransferase/oxoacyl-CoA thiolase A (EC 2.3.1.16, SCP2/3-oxoacyl-CoA thiolase) present in peroxisomes from normal liver. Peroxisomes beta -oxidize a wide variety of substrates including straight chain fatty acids, 2-methyl-branched fatty acids, and the side chain of the bile acid intermediates di- and trihydroxycoprostanic acids. Peroxisomes contain several beta -oxidation pathways with different substrate specificities; or example, straight chain acyl-CoAs are desaturated by palmitoyl-CoA oxidase, and their enoyl-CoAs are then converted to 3-oxoacyl-CoAs by MFP-1, which forms (hydration) and dehydrogenates L-3(3S)-hydroxyacyl-CoAs; for example, straight chain acyl-CoAs are desaturated by palmitoyl-CoA oxidase (23), and their enoyl-CoAs are then converted to 3-oxoacyl-CoAs by 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35), which forms (hydration) and dehydrogenates L-3(3S)-hydroxyacyl-CoAs and their enoyl-CoAs are then converted to the corresponding 3-oxoacyl-CoAs by long-chain-enoyl-CoA hydratase(EC 4.2.1.74), which forms and dehydrogenates D-3(3R)-hydroxyacyl-CoAs. (PMID: 9325339). 3-Oxooctanoyl-CoA is the substrate of the acetyl-CoA C-acyltransferase/oxoacyl-CoA thiolase A (EC 2.3.1.16, SCP2/3-oxoacyl-CoA thiolase) present in peroxisomes from normal liver.
3-Oxohexanoyl-CoA
3-Oxohexanoyl-CoA is an intermediate in Fatty acid elongation in mitochondria. 3-Oxohexanoyl-CoA is the 3rd to last step in the synthesis of Hexanoyl-CoA and is converted from Butanoyl-CoA via the enzyme acetyl-CoA acyltransferase 2 (EC 2.3.1.16). It is then converted to (S)-Hydroxyhexanoyl-CoA via the 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35). [HMDB]. 3-Oxohexanoyl-CoA is found in many foods, some of which are soy bean, cloudberry, other bread, and lemon thyme. 3-Oxohexanoyl-CoA is an intermediate in Fatty acid elongation in mitochondria. 3-Oxohexanoyl-CoA is the 3rd to last step in the synthesis of Hexanoyl-CoA and is converted from Butanoyl-CoA via the enzyme acetyl-CoA acyltransferase 2 (EC 2.3.1.16). It is then converted to (S)-Hydroxyhexanoyl-CoA via the 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35).
Hexanoyl-CoA
C27H46N7O17P3S (865.1883656000001)
Hexanoyl-CoA, also known as hexanoyl-coenzyme A or caproyl-CoA, is a medium-chain fatty acyl-CoA having hexanoyl as the acyl group. Hexanoyl-CoA is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Within the cell, hexanoyl-CoA is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. Hexanoyl-CoA exists in all living organisms, ranging from bacteria to humans. In humans, hexanoyl-CoA is involved in the biosynthesis and oxidation of fatty acids as well as in ceramide formation. Hexanoyl-CoA is also involved in few metabolic disorders, such as fatty acid elongation in mitochondria, mitochondrial beta-oxidation of medium chain saturated fatty acids, and mitochondrial beta-oxidation of short chain saturated fatty acids. Fatty acid coenzyme A derivative that can be involved in the biosynthesis and oxidation of fatty acids as well as in ceramide formation. [HMDB]
3-Hydroxyisovaleryl-CoA
3-Hydroxyisovaleryl-CoA is an end product of leucine degradation. It is converted from 3-methylbut-2-enoyl-CoA by the enzyme enoyl-CoA hydratase. [HMDB] 3-Hydroxyisovaleryl-CoA is an end product of leucine degradation. It is converted from 3-methylbut-2-enoyl-CoA by the enzyme enoyl-CoA hydratase.
Mesaconyl-CoA
This compound belongs to the family of Acyl CoAs. These are organic compounds contaning a coenzyme A substructure linked to another moeity through an ester bond.
Malonamoyl-CoA
An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of malonamic acid.
2-Hydroxyphytanoyl-CoA
C41H74N7O18P3S (1077.4023694000002)
2-Hydroxyphytanoyl-CoA is a substrate for Phytanoyl-CoA dioxygenase (peroxisomal). [HMDB] 2-Hydroxyphytanoyl-CoA is a substrate for Phytanoyl-CoA dioxygenase (peroxisomal).
Thiophene-2-carbonyl-CoA
C26H38N7O17P3S2 (877.0978408000001)
An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of thiophene-2-carboxylic acid.
Naphthyl-2-methyl-succinyl-CoA
Adipoyl-CoA
Adipoyl-CoA is formed as the degradation beta-oxidation product (CoA ester) of the dicarboxylic acid formed via w-oxidation of fatty acids in the endoplasmic reticulum. Fatty acid oxidation is an important source of energy, especially during fasting and diabetes. Although mitochondria are considered the primary site for beta-oxidation of fatty acids for energy utilization, peroxisomes play a key role in the metabolism of a variety of lipids such as very long-chain fatty acids, branched-chain fatty acids, dicarboxylic fatty acids, bile acid intermediates, prostaglandins, leukotrienes, thromboxanes, pristanic acid, and xenobiotic carboxylic acids. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A. Acyl-CoA hydrolase 8 (ACOT8, EC 3.1.2.20) preferentially hydrolyzes medium-chain dicarboxylyl-CoA esters such as Adipoyl-CoA and is responsible for the termination of beta-oxidation of dicarboxylic acids of medium-chain length with the concomitant release of the corresponding free acids. In mitochondria, Adipoyl-CoA is a substrate of the enzyme Hydroxymethylglutarate coenzyme A-transferase (E.C. 2.8.3.13). Both synthesis and degradation of dicarboxylic acids occur mainly in kidney and liver, and the chain-shortened dicarboxylic acids are excreted in the urine as the free acids. (PMID: 16141203) [HMDB] Adipoyl-CoA is formed as the degradation beta-oxidation product (CoA ester) of the dicarboxylic acid formed via w-oxidation of fatty acids in the endoplasmic reticulum. Fatty acid oxidation is an important source of energy, especially during fasting and diabetes. Although mitochondria are considered the primary site for beta-oxidation of fatty acids for energy utilization, peroxisomes play a key role in the metabolism of a variety of lipids such as very long-chain fatty acids, branched-chain fatty acids, dicarboxylic fatty acids, bile acid intermediates, prostaglandins, leukotrienes, thromboxanes, pristanic acid, and xenobiotic carboxylic acids. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A. Acyl-CoA hydrolase 8 (ACOT8, EC 3.1.2.20) preferentially hydrolyzes medium-chain dicarboxylyl-CoA esters such as Adipoyl-CoA and is responsible for the termination of beta-oxidation of dicarboxylic acids of medium-chain length with the concomitant release of the corresponding free acids. In mitochondria, Adipoyl-CoA is a substrate of the enzyme Hydroxymethylglutarate coenzyme A-transferase (E.C. 2.8.3.13). Both synthesis and degradation of dicarboxylic acids occur mainly in kidney and liver, and the chain-shortened dicarboxylic acids are excreted in the urine as the free acids. (PMID: 16141203).
Deoxycholoyl-CoA
A steroidal acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of deoxycholic acid.
3-Oxooctadecanoyl-CoA
3-Oxooctadecanoyl-CoA is a metabolite intermediate in the microsomal fatty acid chain elongation system. Microsomal electron-transport components NADPH-cytochrome P450 reductase (EC 1.6.2.4) and cytochrome b5 (EC 1.6.2.2) participate in the conversion from 3-Oxooctadecanoyl-CoA to beta-hydroxystearoyl-CoA, the first reductive step of the microsomal chain elongating system initiated by NADPH. (PMID: 6404652) [HMDB] 3-Oxooctadecanoyl-CoA is a metabolite intermediate in the microsomal fatty acid chain elongation system. Microsomal electron-transport components NADPH-cytochrome P450 reductase (EC 1.6.2.4) and cytochrome b5 (EC 1.6.2.2) participate in the conversion from 3-Oxooctadecanoyl-CoA to beta-hydroxystearoyl-CoA, the first reductive step of the microsomal chain elongating system initiated by NADPH. (PMID: 6404652).
3-hydroxyoctadecanoyl-CoA
3-hydroxyoctadecanoyl-CoA is a human metabolite involved in the fatty acid elongation in mitochondria pathway. The enzyme long-chain-3-hydroxyacyl-CoA dehydrogenase catalyzes the conversion of 3-Oxododecanoyl-CoA to (S)-3-Hydroxydodecanoyl-CoA.3-hydroxyoctadecanoyl-CoA is an intermediate in fatty acid metabolism, being the substrate of the enzymes beta-hydroxyacyl-CoA dehydrogenase and 3-hydroxyacyl-CoA dehydrogenase [EC 1.1.1.211-1.1.1.35]; 3-hydroxyoctadecanoyl-CoA is an intermediate in fatty acid elongation in mitochondria, the substrate of the enzymes enoyl-CoA hydratase and long-chain-enoyl-CoA hydratase [EC 4.2.1.17-4.2.1.74]. (KEGG).
11Z-eicosenoyl-CoA
11Z-eicosenoyl-CoA is classified as a member of the Long-chain fatty acyl CoAs. Long-chain fatty acyl CoAs are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. 11Z-eicosenoyl-CoA is considered to be practically insoluble (in water) and acidic. 11Z-eicosenoyl-CoA is a fatty ester lipid molecule
15Z-tetracosenoyl-CoA
C45H80N7O17P3S (1115.4544020000003)
15z-tetracosenoyl-coa, also known as nervonoyl-coa, is a member of the class of compounds known as very long-chain fatty acyl coas. Very long-chain fatty acyl coas are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more. Thus, 15z-tetracosenoyl-coa is considered to be a fatty ester lipid molecule. 15z-tetracosenoyl-coa is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). 15z-tetracosenoyl-coa can be found in a number of food items such as hazelnut, sugar apple, cardamom, and ginkgo nuts, which makes 15z-tetracosenoyl-coa a potential biomarker for the consumption of these food products. In humans, 15z-tetracosenoyl-coa is involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(24:1(15Z)/22:4(7Z,10Z,13Z,16Z)/18:3(6Z,9Z,12Z)), de novo triacylglycerol biosynthesis TG(24:1(15Z)/22:1(13Z)/20:5(5Z,8Z,11Z,14Z,17Z)), de novo triacylglycerol biosynthesis TG(20:0/24:1(15Z)/20:4(5Z,8Z,11Z,14Z)), and de novo triacylglycerol biosynthesis TG(24:0/22:2(13Z,16Z)/24:1(15Z)). 15Z-tetracosenoyl-CoA is classified as a member of the Very long-chain fatty acyl CoAs. Very long-chain fatty acyl CoAs are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more. 15Z-tetracosenoyl-CoA is considered to be practically insoluble (in water) and acidic. 15Z-tetracosenoyl-CoA is a fatty ester lipid molecule
feruloylacetyl-CoA
C33H46N7O20P3S (985.1731106000001)
An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of feruloylacetic acid.
2-oxoglutaryl-CoA
An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the 1-carboxy group of 2-oxoglutaric acid.
gamma-butyrobetainyl-CoA
An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 4-trimethylammoniobutanoic acid.
Hexacosanoyl-CoA
C47H86N7O17P3S (1145.5013496000001)
Hexacosanoyl-coa, also known as C26:0-CoA, C26:0-coenzyme A, or cerotoyl-CoA is an acyl-CoA or acyl-coenzyme A. More specifically, it is a hexacosanoic acid thioester of coenzyme A. Hexacosanoyl-coa is an acyl-CoA with 26 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. Hexacosanoyl-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. Hexacosanoyl-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, Hexacosanoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of Hexacosanoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts Hexacosanoyl-CoA into Hexacosanoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, Hexacosanoylcarnitine is converted back to Hexacosanoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of Hexacosanoyl-CoA occurs in four steps. First, since Hexacosanoyl-CoA is a very long chain acyl-CoA it is the substrate for a very long chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of Hexacosanoyl-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 gro... hexacosanoyl CoA is an intermediate in Biosynthesis of fatty acids. hexacosanoyl CoA (26:O CoA) oxidation was detected in peroxisomal and
cis-Vaccenoyl CoA
Vaccenoyl CoA is a coenzyme A derivative of vaccenic acid. There are both cis (or R) and trans (or S) forms of Vaccenoyl CoA. Vaccenoyl CoA derivatives were found to be active substrates in vitro in the acylation of glycerol 3-phosphate. It is involved in the biosynthesis and oxidation of fatty acids as well as in ceramide formation. [HMDB] Vaccenoyl CoA is a coenzyme A derivative of vaccenic acid. There are both cis (or R) and trans (or S) forms of Vaccenoyl CoA. Vaccenoyl CoA derivatives were found to be active substrates in vitro in the acylation of glycerol 3-phosphate. It is involved in the biosynthesis and oxidation of fatty acids as well as in ceramide formation.
Tetracosanoyl-CoA
Tetracosanoyl-CoA is an intermediate in the biosynthesis of unsaturated fatty acids. Tetracosanoyl-CoA is converted from Palmitoyl-CoA in multiple steps. It is then converted to lignoceric acid via a thiol-ester hydrolase (E 3.1.2.-). [HMDB] Tetracosanoyl-CoA is an intermediate in the biosynthesis of unsaturated fatty acids. Tetracosanoyl-CoA is converted from Palmitoyl-CoA in multiple steps. It is then converted to lignoceric acid via a thiol-ester hydrolase (E 3.1.2.-).
Methylmalonyl-CoA
A member of the class of malonyl-CoAs that is malonyl-CoA carrying a methyl group on the malony side chain.
Butyryl-CoA
C25H42N7O17P3S (837.1570672000001)
Butyryl-CoA is an intermediate in the metabolism of Butanoate. It is a substrate for Acyl-coenzyme A oxidase 3 (peroxisomal), 3-ketoacyl-CoA thiolase (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal), Acyl-coenzyme A oxidase 1 (peroxisomal), Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial), Acyl-CoA dehydrogenase (long-chain specific, mitochondrial), Acyl-coenzyme A oxidase 2 (peroxisomal), Acetyl-CoA acetyltransferase (mitochondrial), Acetyl-CoA acetyltransferase (cytosolic), Acyl-CoA dehydrogenase (short-chain specific, mitochondrial) and Trifunctional enzyme beta subunit (mitochondrial).
Deoxycholoyl-CoA
This compound belongs to the family of Acyl CoAs. These are organic compounds contaning a coenzyme A substructure linked to another moeity through an ester bond.
3-Hydroxyhexacosanoyl-CoA
3-Hydroxyhexacosanoyl-CoA is also known as 3-Hydroxyhexacosanoyl-coenzyme A(4-)
3-Oxotetracosanoyl-CoA
This compound belongs to the family of 3-Oxo-acyl CoAs. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
3-Hydroxytetracosanoyl-CoA
C45H82N7O18P3S (1133.4649662000002)
3-Hydroxytetracosanoyl-CoA, also known as 3-hydroxylignoceroyl-CoA, belongs to the class of organic compounds known as very-long-chain (3R)-3-hydroxyacyl-CoAs. These are organic compounds containing a (R)-3-hydroxyl acylated coenzyme A derivative, to which the acyl chain carries at least 22 carbon atoms. 3-Hydroxytetracosanoyl-CoA is a strong basic compound (based on its pKa).
3-Oxodocosanoyl-CoA
C43H76N7O18P3S (1103.4180185999999)
This compound belongs to the family of 3-Oxo-acyl CoAs. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
3-Hydroxydocosanoyl-CoA
3-Hydroxydocosanoyl-CoA, also known as 3-hydroxybehenoyl-CoA, belongs to the class of organic compounds known as very-long-chain (3R)-3-hydroxyacyl-CoAs. These are organic compounds containing an (R)-3-hydroxyl acylated coenzyme A derivative, to which the acyl chain carries at least 22 carbon atoms. 3-Hydroxydocosanoyl-CoA is a strong basic compound (based on its pKa).
3-Oxoicosanoyl-CoA
C41H72N7O18P3S (1075.3867202000001)
This compound belongs to the family of 3-Oxo-acyl CoAs. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
trans,cis-Lauro-2,6-dienoyl-CoA
Trans,cis-Lauro-2,6-dienoyl-CoA is a co-enzyme A intermediate that participates in fatty acid metabolism, especially long chain fatty acid biosynthesis. trans,cis-Lauro-2,6-dienoyl-CoA is converted from cis,cis-3,6-Dodecadienoyl-CoA via the enzyme known as dodecenoyl-CoA delta-isomerase [EC:5.3.3.8] and vice-versa. Fatty acid degradation is the process in which fatty acids are broken down, resulting in release of energy. It includes three major steps: Activation and transport into mitochondria, β-oxidation and movement through the electron transport chain. Fatty acids are transported across the outer mitochondrial membrane by carnitine-palmitoyl transferase I (CPT-I), and then couriered across the inner mitochondrial membrane by carnitine (PMID:11413487). Once inside the mitochondrial matrix, fatty acyl-carnitine reacts with coenzyme A to release the fatty acid and produce acetyl-CoA. CPT-I is believed to be the rate limiting step in fatty acid oxidation. Once inside the mitochondrial matrix, fatty acids undergo β-oxidation (PMID: 25703630). During this process, two-carbon molecules (in the form of acetyl-CoA) are repeatedly cleaved from the fatty acid. Acetyl-CoA can then enter the TCA cycle, which produces NADH and FADH. NADH and FADH are subsequently used in the electron transport chain to produce ATP, the energy currency of the cell. trans,cis-Lauro-2,6-dienoyl-CoA participates in fatty acid metabolism. trans,cis-Lauro-2,6-dienoyl-CoA is converted from cis,cis-3,6-Dodecadienoyl-CoA via dodecenoyl-CoA delta-isomerase [EC:5.3.3.8] and vice-versa.
2-Methylhexanoyl-CoA
2-Methylhexanoyl-CoA is a coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is adapted from cysteamine, pantothenate, and adenosine triphosphate. This compound is formed by 2-Methylhexanoic acid reacting with thiol group of CoA molecules. [HMDB] 2-Methylhexanoyl-CoA is a coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is adapted from cysteamine, pantothenate, and adenosine triphosphate. This compound is formed by 2-Methylhexanoic acid reacting with thiol group of CoA molecules.
Heptanoyl-CoA
Heptanoyl-CoA is an acyl-CoA with the C-7 fatty acid Acyl chain moiety. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine. Heptanoyl-CoA is a acyl-CoA with the C-7 fatty acid Acyl chain moiety.
Tridecanoyl-CoA
C34H60N7O17P3S (963.2979100000001)
Tridecanoyl-CoA is an acyl-CoA with C-13 fatty acid group as the acyl moiety. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid inside living cells. The compound undergoes beta oxidation, forming one or more molecules of acetyl-CoA. This, in turn, enters the citric acid cycle, eventually forming several molecules of ATP. Tridecanoyl-CoA is involved in Phytanic acid peroxisomal oxidation pathway as an intermediate reduction product. Tridecanoyl-CoA is an acyl-CoA with C-13 fatty acid group as the acyl moiety.
Undecanoyl-CoA
C32H56N7O17P3S (935.2666116000001)
Undecanoyl CoA is an acyl-CoA with the C-11 Acyl chain. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine. Undecanoyl coA is a acyl-CoA with the C-11 Acyl chain.
Valproyl-CoA
C29H50N7O17P3S (893.2196640000001)
Valproyl-CoA, a valproate metabolite previously identified in liver, may accumulate in brain as a result of normal fatty acid turnover processes. Valproyl CoA could contribute to valproates antiepileptic activity by stimulating Na+, K+-ATPase activity when brain ATP concentration is low. Valproyl-CoA and to a much lesser extent 3-keto-valproyl-CoA are the main metabolites of VPA in mitochondria. Valproyl-CoA, a valproate metabolite previously identified in liver, may accumulate in brain as a result of normal fatty acid turnover processes. Valproyl CoA could contribute to valproates antiepileptic activity by stimulating Na+, K+-ATPase activity when brain ATP concentration is low.
3-Oxopristanoyl-CoA
This compound belongs to the family of 3-Oxo-acyl CoAs. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
3-hydroxypristanoyl-CoA
C40H72N7O18P3S (1063.3867202000001)
3-hydroxypristanoyl-CoA is also known as 3-Hydroxy-2,6,10,14-tetramethylpentadecanoyl-CoA. 3-hydroxypristanoyl-CoA is considered to be slightly soluble (in water) and acidic. 3-hydroxypristanoyl-CoA is a fatty ester lipid molecule
3-Oxohexacosanoyl-CoA
C47H84N7O18P3S (1159.4806154000003)
3-Oxohexacosanoyl-CoA is also known as 3-Ketocerotoyl-CoA(4-) or 3-Ketohexacosanoyl-coenzyme A(4-). 3-Oxohexacosanoyl-CoA is considered to be practically insoluble (in water) and acidic COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
5Z-tetradecenoyl-CoA
C35H60N7O17P3S (975.2979100000001)
5Z-tetradecenoyl-CoA is also known as 14:1(N-9)-CoA or (cis-Delta(5))-Tetradecanoyl-CoA. 5Z-tetradecenoyl-CoA is considered to be slightly soluble (in water) and acidic. 5Z-tetradecenoyl-CoA is a fatty ester lipid molecule
Isotridecanoyl-CoA
C34H60N7O17P3S (963.2979100000001)
A methyl-branched fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of isotridecanoic acid (ChEBI: 71437).
Isopentadecanoyl-CoA
C36H64N7O17P3S (991.3292084000001)
A methyl-branched fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of isopentadecanoic acid.
Isoheptadecanoyl-CoA
A methyl-branched fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of isoheptadecanoic acid.
5-hydroxypentanoyl-CoA
5-hydroxypentanoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a 5-hydroxypentanoic acid thioester of coenzyme A. 5-hydroxypentanoyl-coa is an acyl-CoA with 5 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. 5-hydroxypentanoyl-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. 5-hydroxypentanoyl-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, 5-hydroxypentanoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of 5-hydroxypentanoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts 5-hydroxypentanoyl-CoA into 5-hydroxypentanoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, 5-hydroxypentanoylcarnitine is converted back to 5-hydroxypentanoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of 5-hydroxypentanoyl-CoA occurs in four steps. First, since 5-hydroxypentanoyl-CoA is a medium chain acyl-CoA it is the substrate for a medium chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of 5-hydroxypentanoyl-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 alc...
3-methylbut-2-enoyl-CoA
C26H42N7O17P3S (849.1570672000001)
3-methylbut-2-enoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a 3-methylbut-2-enoic acid thioester of coenzyme A. 3-methylbut-2-enoyl-coa is an acyl-CoA with 4 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. 3-methylbut-2-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. 3-methylbut-2-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, 3-methylbut-2-enoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of 3-methylbut-2-enoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts 3-methylbut-2-enoyl-CoA into 3-methylbut-2-enoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, 3-methylbut-2-enoylcarnitine is converted back to 3-methylbut-2-enoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of 3-methylbut-2-enoyl-CoA occurs in four steps. First, since 3-methylbut-2-enoyl-CoA is a short chain acyl-CoA it is the substrate for a short chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of 3-methylbut-2-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 oxidize...
decanoyl-CoA
Decanoyl-coa, also known as 10:0-coa or decanoyl-coenzyme a, is a member of the class of compounds known as 2,3,4-saturated fatty acyl coas. 2,3,4-saturated fatty acyl coas are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain. Thus, decanoyl-coa is considered to be a fatty ester lipid molecule. Decanoyl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Decanoyl-coa can be synthesized from decanoic acid and coenzyme A. Decanoyl-coa can also be synthesized into 3-oxodecanoyl-CoA. Decanoyl-coa can be found in a number of food items such as swede, triticale, ohelo berry, and moth bean, which makes decanoyl-coa a potential biomarker for the consumption of these food products. Decanoyl-coa may be a unique S.cerevisiae (yeast) metabolite.
Tetracosanoyl-CoA
Tetracosanoyl-CoA is an intermediate in the biosynthesis of unsaturated fatty acids. Tetracosanoyl-CoA is converted from Palmitoyl-CoA in multiple steps. It is then converted to lignoceric acid via a thiol-ester hydrolase (E 3.1.2.-). [HMDB] Tetracosanoyl-CoA is an intermediate in the biosynthesis of unsaturated fatty acids. Tetracosanoyl-CoA is converted from Palmitoyl-CoA in multiple steps. It is then converted to lignoceric acid via a thiol-ester hydrolase (E 3.1.2.-).
Acetyl-CoA
C23H38N7O17P3S (809.1257688000001)
An acyl-CoA having acetyl as its S-acetyl component.
Malyl-CoA
oleoyl-CoA
An octadecenoyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of oleic acid.
Lactyl-CoA
An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of lactic acid.
3-oxodecanoyl-CoA
C31H52N7O18P3S (935.2302281999999)
An oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxylic acid group of 3-oxodecanoic acid.
3-Oxodocosanoyl-CoA
C43H76N7O18P3S (1103.4180185999999)
A 3-oxo-fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxodocosanoic acid.
3-oxohexacosanoyl-CoA
C47H84N7O18P3S (1159.4806154000003)
A 3-oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxohexacosanoic acid.
3-Oxolauroyl-CoA
C33H56N7O18P3S (963.2615266000001)
An oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxylic acid group of 3-oxolauroic acid.
3-oxopalmitoyl-CoA
C37H64N7O18P3S (1019.3241234000001)
The S-(3-oxopalmitoyl) derivative of coenzyme A.
3-Oxotetracosanoyl-CoA
A 3-oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxotetracosanoic acid.
Glutaryl-CoA
C26H42N7O19P3S (881.1468972000001)
An omega-carboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of glutaric acid.
Itaconyl-CoA
The S-itaconyl derivative of coenzyme A.
pimeloyl-CoA
C28H46N7O19P3S (909.1781956000001)
An omega carboxyacyl-CoA that is the S-pimeloyl derivative of coenzyme A.
Succinyl-CoA
An omega-carboxyacyl-CoA having succinoyl as the S-acyl component.
Linoleoyl-CoA
An octadecadienoyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of linoleic acid. Linoleoyl-CoA is the acyl-CoA of linoleic acid found in the human body. It binds to and results in decreased activity of Glutathione S-transferase1. It has been proposed that inhibition of mitochondrial adenine nucleotide translocator by long chain acyl-CoA underlies the mechanism associating obesity and type 2 diabetes. Unsaturated fatty acids play an important role in the prevention of human diseases such as diabetes, obesity, cancer, and neurodegeneration. Their oxidation in vivo by acyl-CoA dehydrogenases (ACADs) catalyze the first step of each cycle of mitochondrial fatty acid {beta}-oxidation; ACAD-9 had maximal activity with long-chain unsaturated acyl-CoAs as substrates. (PMID: 17184976, 16020546) [HMDB]
Heptanoyl-CoA
Heptanoyl-CoA is an acyl-CoA with the C-7 fatty acid Acyl chain moiety. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine. Heptanoyl-CoA is a acyl-CoA with the C-7 fatty acid Acyl chain moiety.
Nonanoyl-CoA
C30H52N7O17P3S (907.2353132000001)
Nonanoyl CoA is an acyl-CoA with the C-9 fatty acid Acyl chain moiety. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine. Nonanoyl coA is a acyl-CoA with the C-9 fatty acid Acyl chain moiety.
Pentanoyl-CoA
Pentanoyl CoA is an acyl-CoA with the C-5 Acyl chain. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine. Pentanoyl coA is a acyl-CoA with the C-5 Acyl chain.
2-Hydroxyphytanoyl-CoA
C41H74N7O18P3S (1077.4023694000002)
A multi-methyl-branched fatty acyl-CoA having 2-hydroxyphytanoyl as the S-acyl group.
cis-geranoyl-CoA
C31H50N7O17P3S (917.2196640000001)
The S-geranoyl derivative of coenzyme A.
3-hydroxyoctanoyl-CoA
C29H50N7O18P3S (909.2145790000001)
A 3-hydroxy-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-hydroxyoctanoic acid.
Acetoacetyl-CoA
A 3-oxoacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of acetoacetic acid.
acryloyl-CoA
C24H38N7O17P3S (821.1257688000001)
The S-acryloyl derivative of coenzyme A.
Methacrylyl-CoA
An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of methacrylic acid.
Lauroyl-CoA
A medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of lauric (dodecanoic) acid.
palmitoyl-CoA
A long-chain fatty acyl-CoA resulting from the formal condensation of the carboxy group of hexadecanoic acid with the thiol group of coenzyme A. COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
decanoyl-CoA
A medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of decanoic acid.
Propionyl-CoA
An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of propionic acid.
Hexanoyl-CoA
C27H46N7O17P3S (865.1883656000001)
A medium-chain fatty acyl-CoA having hexanoyl as the S-acyl group.
Isobutyryl-CoA
C25H42N7O17P3S (837.1570672000001)
A short-chain, methyl-branched fatty acyl-CoA that is the S-isobutyryl derivative of coenzyme A.
palmitoleoyl-CoA
C37H64N7O17P3S (1003.3292084000001)
A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of palmitoleic acid.
Butyryl-CoA
C25H42N7O17P3S (837.1570672000001)
A short-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of butyric acid.
Hexacosanoyl-CoA
C47H86N7O17P3S (1145.5013496000001)
A very long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of hexacosanoic (cerotic) acid..
gamma-linolenoyl-CoA
An octadecatrienoyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of gamma-linolenic acid.
stearoyl-CoA
A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of stearic acid.
myristoyl-CoA
A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of myristic acid.
Phenylacetyl-CoA
C29H42N7O17P3S (885.1570672000001)
An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of phenylacetic acid.
3-oxoadipyl-CoA
C27H42N7O20P3S (909.1418122000001)
The S-(3-oxoadipyl) derivative of coenzyme A.
3-Oxohexanoyl-CoA
An oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxylic acid group of 3-oxohexanoic acid.
3-methylbut-2-enoyl-CoA
C26H42N7O17P3S (849.1570672000001)
An unsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-methylbut-2-enoic acid.
Mesaconyl-CoA
An omega-carboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the 1-carboxy group of mesaconic acid.
3-Oxooctanoyl-CoA
An oxo-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxylic acid group of 3-oxooctanoic acid.
2-methylbutanoyl-CoA
A short-chain, methyl-branched fatty acyl-CoA having 2-methylbutanoyl as the S-acyl group.
2-Methylacetoacetyl-CoA
C26H42N7O18P3S (865.1519822000001)
A 3-oxoacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 2-methylacetoacetic acid.
Cinnamoyl-CoA
C30H42N7O17P3S (897.1570672000001)
An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of cinnamic acid.
Nonanoyl-CoA
C30H52N7O17P3S (907.2353132000001)
A medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of nonanoic acid.
Choloyl-CoA
C45H74N7O20P3S (1157.3921994000002)
A steroidal acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of cholic acid. D005765 - Gastrointestinal Agents > D001647 - Bile Acids and Salts D005765 - Gastrointestinal Agents > D002793 - Cholic Acids
3-hydroxyisovaleryl-CoA
A hydroxy fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-hydroxyisovaleric acid.
3-Oxopristanoyl-CoA
A multi-methyl-branched fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxopristanic acid.
cyclohexa-1,5-diene-1-carbonyl-CoA
C28H42N7O17P3S (873.1570672000001)
pentanoyl-CoA
A short-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of pentanoic acid.
Beta-Alanyl-CoA
C24H41N8O17P3S (838.1523166000001)
An acyl-CoA that is the S-(beta-alanyl) derivative of coenzyme A.
3-(4-methylpent-3-en-1-yl)pent-2-enedioyl-CoA
C32H50N7O19P3S (961.2094940000001)
montanoyl-CoA
C49H90N7O17P3S (1173.5326479999999)
A very long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of montanic acid.
Heptadecanoyl-CoA
A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of heptadecanoic acid,
3-Oxoicosanoyl-CoA
C41H72N7O18P3S (1075.3867202000001)
A 3-oxoacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxoicosanoic acid.
Heptanoyl-CoA
A medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of heptanoic acid.
3-Hydroxytetracosanoyl-CoA
C45H82N7O18P3S (1133.4649662000002)
A very long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-hydroxytetracosanoic acid.
isopentadecanoyl-CoA
C36H64N7O17P3S (991.3292084000001)
A methyl-branched fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of isopentadecanoic acid.
3-hydroxyadipyl-CoA
An acyl-CoA that results from formal condensation of the thiol group of coenzyme A with the 1-carboxy group of 3-hydroxyadipic acid.
isoheptadecanoyl-CoA
A methyl-branched fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of isoheptadecanoic acid.
isotridecanoyl-CoA
C34H60N7O17P3S (963.2979100000001)
A methyl-branched fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of isotridecanoic acid
3-hydroxypristanoyl-CoA
C40H72N7O18P3S (1063.3867202000001)
A multi-methyl-branched fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-hydroxypristanic acid.
3-hydroxy-3-methylglutaryl-CoA
An alpha,omega dicarboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-methylglutaric acid.
3-hydroxyicosanoyl-CoA
C41H74N7O18P3S (1077.4023694000002)
A 3-hydroxy fatty acyl-CoA in which the 3-hydroxy fatty acyl group is specified as 3-hydroxyicosanoyl.
Undecanoyl-CoA
C32H56N7O17P3S (935.2666116000001)
A medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of undecanoic acid.
2-Methylhexanoyl-CoA
A medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 2-methylhexanoic acid.
Tridecanoyl-CoA
C34H60N7O17P3S (963.2979100000001)
A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of tridecanoic acid.
3-Hydroxydocosanoyl-CoA
A 3-hydroxy fatty acyl-CoA in which the 3-hydroxy fatty acyl group is specified as 3-hydroxydocosanoyl.
2-hydroxyadipoyl-CoA
A hydroxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the 1-carboxy group of 2-hydroxyadipic acid.
3-hydroxyhexacosanoyl-CoA
A 3-hydroxy fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-hydroxyhexacosanoic acid.
2-hydroxypalmitoyl-CoA
A hydroxy fatty-acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 2-hydroxypalmitic acid.
L-erythro-3-methylmalyl-CoA
C26H42N7O20P3S (897.1418122000001)
A hydroxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of L-erythro-3-methylmalic acid.
2-hydroxybehenoyl-CoA
A hydroxy fatty-acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 2-hydroxybehenic acid.
3-oxoisooctadecanoyl-CoA
A methyl-branched fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxoisooctadecanoic acid.
3-oxoisoheptadecanoyl-CoA
A methyl-branched fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxoisoheptadecanoic acid.
3-oxoisopentadecanoyl-CoA
A methyl-branched fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxoisopentadecanoic acid.
2-hydroxytetracosanoyl-CoA
C45H82N7O18P3S (1133.4649662000002)
A hydroxy fatty-acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 2-hydroxytetracosanoic acid.
3-hydroxyisopentadecanoyl-CoA
C36H64N7O18P3S (1007.3241234000001)
A methyl-branched fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-hydroxyisopentadecanoic acid.
3-hydroxyisoheptadecanoyl-CoA
A methyl-branched fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-hydroxyisoheptadecanoic acid
trans-feruloyl-CoA
A feruloyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of trans-feruloic acid.
Octanoyl-CoA
C29H50N7O17P3S (893.2196640000001)
A medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of octanoic acid.
isopalmitoyl-CoA
A methyl-branched fatty acyl-CoA obtained from the formal condensation of the thiol group of coenzyme A with the carboxy group of isopalmitic acid
3-hydroxybutanoyl-CoA
C25H42N7O18P3S (853.1519822000001)
A hydroxybutanoyl-CoA having 3-hydroxybutanoyl as the S-acyl component.
3-Hydroxydecanoyl-CoA
A 3-hydroxy-fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-hydroxydecanoic acid.
2-hydroxystearoyl-CoA
A hydroxy fatty-acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 2-hydroxystearic acid.
Pentadecanoyl-CoA/Hydroxytetradecenoyl-CoA
C35H60N7O18P3S (991.2928250000001)