| Record Information |
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| Version | 5.0 |
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| Status | Predicted |
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| Creation Date | 2021-09-22 01:34:27 UTC |
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| Update Date | 2021-10-01 16:55:08 UTC |
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| HMDB ID | HMDB0301622 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-CoA |
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| Description | (5z)-7-{2-[(1e,3r)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a (5Z)-7-{2-[(1E_3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid thioester of coenzyme A. (5z)-7-{2-[(1e,3r)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-coa is an acyl-CoA with 20 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. (5z)-7-{2-[(1e,3r)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-coa is therefore classified as a 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. (5z)-7-{2-[(1e,3r)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-coa, being a long chain acyl-CoA is a substrate for 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, (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-CoA into (5Z)-7-{2-[(1E_3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, (5Z)-7-{2-[(1E_3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoylcarnitine is converted back to (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-CoA occurs in four steps. First, since (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-CoA is a long chain acyl-CoA it is the substrate for a long chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-CoA, creating a double bond between the alpha and beta carbons. FAD is the hydrogen acceptor, yielding FADH2. Second, Enoyl-CoA hydrase catalyzes the addition of water across the newly formed double bond to make an alcohol. Third, 3-hydroxyacyl-CoA dehydrogenase oxidizes the alcohol group to a ketone and NADH is produced from NAD+. Finally, 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 (5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoyl-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. | Read more...
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| Structure | CCCCCC(O)C=CC1=C(CC=CCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2OP(O)(O)=O)N2C=NC3=C2N=CN=C3N)C(=O)CC1 InChI=1S/C41H64N7O19P3S/c1-4-5-8-11-27(49)16-14-26-15-17-29(50)28(26)12-9-6-7-10-13-32(52)71-21-20-43-31(51)18-19-44-39(55)36(54)41(2,3)23-64-70(61,62)67-69(59,60)63-22-30-35(66-68(56,57)58)34(53)40(65-30)48-25-47-33-37(42)45-24-46-38(33)48/h6,9,14,16,24-25,27,30,34-36,40,49,53-54H,4-5,7-8,10-13,15,17-23H2,1-3H3,(H,43,51)(H,44,55)(H,59,60)(H,61,62)(H2,42,45,46)(H2,56,57,58) |
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| Synonyms | | Value | Source |
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| 4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-(2-{[2-({7-[2-(3-hydroxyoct-1-en-1-yl)-5-oxocyclopent-1-en-1-yl]hept-5-enoyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidate | HMDB | | 4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-(2-{[2-({7-[2-(3-hydroxyoct-1-en-1-yl)-5-oxocyclopent-1-en-1-yl]hept-5-enoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidate | HMDB | | 4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-(2-{[2-({7-[2-(3-hydroxyoct-1-en-1-yl)-5-oxocyclopent-1-en-1-yl]hept-5-enoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-3,3-dimethylbutanimidic acid | HMDB |
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| Chemical Formula | C41H64N7O19P3S |
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| Average Molecular Weight | 1083.97 |
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| Monoisotopic Molecular Weight | 1083.319055037 |
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| IUPAC Name | {[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-3-[(2-{[2-({7-[2-(3-hydroxyoct-1-en-1-yl)-5-oxocyclopent-1-en-1-yl]hept-5-enoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid |
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| Traditional Name | [5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-[(2-{[2-({7-[2-(3-hydroxyoct-1-en-1-yl)-5-oxocyclopent-1-en-1-yl]hept-5-enoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid |
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| CAS Registry Number | Not Available |
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| SMILES | CCCCCC(O)C=CC1=C(CC=CCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2OP(O)(O)=O)N2C=NC3=C2N=CN=C3N)C(=O)CC1 |
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| InChI Identifier | InChI=1S/C41H64N7O19P3S/c1-4-5-8-11-27(49)16-14-26-15-17-29(50)28(26)12-9-6-7-10-13-32(52)71-21-20-43-31(51)18-19-44-39(55)36(54)41(2,3)23-64-70(61,62)67-69(59,60)63-22-30-35(66-68(56,57)58)34(53)40(65-30)48-25-47-33-37(42)45-24-46-38(33)48/h6,9,14,16,24-25,27,30,34-36,40,49,53-54H,4-5,7-8,10-13,15,17-23H2,1-3H3,(H,43,51)(H,44,55)(H,59,60)(H,61,62)(H2,42,45,46)(H2,56,57,58) |
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| InChI Key | YGZFWEGYIKIOPN-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain. |
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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 | 2,3,4-saturated 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
- Beta amino acid or derivatives
- 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
- N-acyl-amine
- Monosaccharide
- Fatty amide
- Heteroaromatic compound
- Tetrahydrofuran
- Imidazole
- Azole
- Carbothioic s-ester
- Cyclic ketone
- Thiocarboxylic acid ester
- Secondary carboxylic acid amide
- Secondary alcohol
- Ketone
- Carboxamide group
- Amino acid or derivatives
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Sulfenyl compound
- Thiocarboxylic acid or derivatives
- Carboxylic acid derivative
- 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 | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | | Show more...
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available | Show more...
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