| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2017-03-23 03:12:12 UTC |
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| Update Date | 2022-03-07 03:17:56 UTC |
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| HMDB ID | HMDB0062537 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Tricosanoyl-CoA |
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| Description | Tricosanoyl-coa, also known as C23-CoA(4-) or tricosanoyl-coenzyme A(4-) is an acyl-CoA or acyl-coenzyme A. More specifically, it is a tricosanoic acid thioester of coenzyme A. Tricosanoyl-coa is an acyl-CoA with 23 fatty acid group as the acyl moiety attached to coenzyme A. Coenzyme A was discovered in 1946 by Fritz Lipmann (Journal of Biological Chemistry (1946) 162 (3): 743–744) and its structure was determined in the early 1950s at the Lister Institute in London. Coenzyme A is a complex, thiol-containing molecule that is naturally synthesized from pantothenate (vitamin B5), which is found in various foods such as meat, vegetables, cereal grains, legumes, eggs, and milk. More specifically, coenzyme A (CoASH or CoA) consists of a beta-mercaptoethylamine group linked to the vitamin pantothenic acid (B5) through an amide linkage and 3'-phosphorylated ADP. Coenzyme A is synthesized in a five-step process that requires four molecules of ATP, pantothenate and cysteine. It is believed that there are more than 1100 types of acyl-CoA’s in the human body, which also corresponds to the number of acylcarnitines in the human body. Acyl-CoAs exists in all living species, ranging from bacteria to plants to humans. The general role of acyl-CoA’s is to assist in transferring fatty acids from the cytoplasm to mitochondria. This process facilitates the production of fatty acids in cells, which are essential in cell membrane structure. Acyl-CoA's are also susceptible to beta oxidation, forming, ultimately, acetyl-CoA. Acetyl-CoA can enter the citric acid cycle, eventually forming several equivalents of ATP. In this way, fats are converted to ATP -- or biochemical energy. Acyl-CoAs can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain acyl-CoAs; 2) medium-chain acyl-CoAs; 3) long-chain acyl-CoAs; and 4) very long-chain acyl-CoAs; 5) hydroxy acyl-CoAs; 6) branched chain acyl-CoAs; 7) unsaturated acyl-CoAs; 8) dicarboxylic acyl-CoAs and 9) miscellaneous acyl-CoAs. Short-chain acyl-CoAs have acyl-groups with two to four carbons (C2-C4), medium-chain acyl-CoAs have acyl-groups with five to eleven carbons (C5-C11), long-chain acyl-CoAs have acyl-groups with twelve to twenty carbons (C12-C20) while very long-chain acyl-CoAs have acyl groups with more than 20 carbons. Tricosanoyl-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. Tricosanoyl-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, Tricosanoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of Tricosanoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts Tricosanoyl-CoA into Tricosanoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, Tricosanoylcarnitine is converted back to Tricosanoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of Tricosanoyl-CoA occurs in four steps. First, since Tricosanoyl-CoA is a very long chain acyl-CoA it is the substrate for a very long chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of Tricosanoyl-CoA, creating a double bond between the alpha and beta carbons. FAD is the hydrogen acceptor, yielding FADH2. Second, Enoyl-CoA hydrase catalyzes the addition of water across the newly formed double bond to make an alcohol. Third, 3-hydroxyacyl-CoA dehydrogenase oxidizes the alcohol group to a ketone and NADH is produced from NAD+. Finally, Thiolase cleaves between the alpha carbon and ketone to release one molecule of acetyl-CoA and a new acyl-CoA which is now 2 carbons shorter. This four-step process repeats until Tricosanoyl-CoA has had all its carbons removed from the chain, leaving only acetyl-CoA. Beta oxidation, as well as alpha-oxidation, also occurs in the peroxisome. The peroxisome handles beta oxidation of fatty acids that have more than 20 carbons in their chain because the peroxisome contains very-long-chain Acyl-CoA synthetases and dehydrogenases. The heart primarily metabolizes fat for energy and Acyl-CoA metabolism has been identified as a critical molecule in early-stage heart muscle pump failure. Cellular acyl-CoA content also correlates with insulin resistance, suggesting that it can mediate lipotoxicity in non-adipose tissues. Acyl-CoA: diacylglycerol acyltransferase (DGAT) plays an important role in energy metabolism on account of key enzyme in triglyceride biosynthesis. The study of acyl-CoAs is an active area of research and it is likely that many novel acyl-CoAs will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules. |
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| Structure | CCCCCCCCCCCCCCCCCCCCCCC(=O)SCCN=C(O)CCN=C(O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 InChI=1S/C44H80N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-35(53)72-28-27-46-34(52)25-26-47-42(56)39(55)44(2,3)30-65-71(62,63)68-70(60,61)64-29-33-38(67-69(57,58)59)37(54)43(66-33)51-32-50-36-40(45)48-31-49-41(36)51/h31-33,37-39,43,54-55H,4-30H2,1-3H3,(H,46,52)(H,47,56)(H,60,61)(H,62,63)(H2,45,48,49)(H2,57,58,59) |
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| Synonyms | | Value | Source |
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| 4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tricosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidate | Generator | | 4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tricosanoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidate | Generator | | 4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tricosanoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid | Generator | | C23-CoA(4-) | HMDB | | Tricosanoyl-coenzyme A(4-) | HMDB |
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| Chemical Formula | C44H80N7O17P3S |
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| Average Molecular Weight | 1104.14 |
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| Monoisotopic Molecular Weight | 1103.454426312 |
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| IUPAC Name | 4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tricosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid |
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| Traditional Name | 4-[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tricosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid |
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| CAS Registry Number | Not Available |
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| SMILES | CCCCCCCCCCCCCCCCCCCCCCC(=O)SCCN=C(O)CCN=C(O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 |
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| InChI Identifier | InChI=1S/C44H80N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-35(53)72-28-27-46-34(52)25-26-47-42(56)39(55)44(2,3)30-65-71(62,63)68-70(60,61)64-29-33-38(67-69(57,58)59)37(54)43(66-33)51-32-50-36-40(45)48-31-49-41(36)51/h31-33,37-39,43,54-55H,4-30H2,1-3H3,(H,46,52)(H,47,56)(H,60,61)(H,62,63)(H2,45,48,49)(H2,57,58,59) |
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| InChI Key | GBAQBZWAXMYXRJ-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Fatty acyl thioesters |
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| Direct Parent | Very long-chain fatty acyl CoAs |
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| Alternative Parents | |
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| Substituents | - Coenzyme a or derivatives
- Purine ribonucleoside diphosphate
- Purine ribonucleoside bisphosphate
- Purine ribonucleoside 3',5'-bisphosphate
- Ribonucleoside 3'-phosphate
- Pentose-5-phosphate
- Pentose phosphate
- N-glycosyl compound
- Glycosyl compound
- Pentose monosaccharide
- Organic pyrophosphate
- Monosaccharide phosphate
- 6-aminopurine
- Purine
- Imidazopyrimidine
- Monoalkyl phosphate
- Aminopyrimidine
- Imidolactam
- Alkyl phosphate
- Pyrimidine
- Phosphoric acid ester
- Organic phosphoric acid derivative
- N-substituted imidazole
- Monosaccharide
- Heteroaromatic compound
- Tetrahydrofuran
- Imidazole
- Azole
- Carbothioic s-ester
- Thiocarboxylic acid ester
- Secondary alcohol
- Amino acid or derivatives
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Sulfenyl compound
- Thiocarboxylic acid or derivatives
- Carboxylic acid derivative
- Carboximidic acid derivative
- Carboximidic acid
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Amine
- Alcohol
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Physiological effect | Not Available |
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| Disposition | Not Available |
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| Process | Not Available |
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| Role | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.03 g/l | ALOGPS | | LogP | 4.74 | ALOGPS |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
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