Record Information |
---|
Version | 5.0 |
---|
Status | Predicted |
---|
Creation Date | 2021-09-22 01:43:57 UTC |
---|
Update Date | 2021-10-01 16:55:10 UTC |
---|
HMDB ID | HMDB0301641 |
---|
Secondary Accession Numbers | None |
---|
Metabolite Identification |
---|
Common Name | (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA |
---|
Description | (4z,7z,10z,13z)-15-{3-[(2z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a (4Z_7Z_10Z_13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4_7_10_13-tetraenoic acid thioester of coenzyme A. (4z,7z,10z,13z)-15-{3-[(2z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-coa is an acyl-CoA with 22 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. (4z,7z,10z,13z)-15-{3-[(2z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-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. (4z,7z,10z,13z)-15-{3-[(2z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-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, (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA into (4Z_7Z_10Z_13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4_7_10_13-tetraenoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, (4Z_7Z_10Z_13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4_7_10_13-tetraenoylcarnitine is converted back to (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA occurs in four steps. First, since (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA is a very long chain acyl-CoA it is the substrate for a very long chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-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 (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-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. |
---|
Structure | CCC=CCC1OC1CC=CCC=CCC=CCC=CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N InChI=1S/C43H66N7O18P3S/c1-4-5-16-19-30-31(65-30)20-17-14-12-10-8-6-7-9-11-13-15-18-21-34(52)72-25-24-45-33(51)22-23-46-41(55)38(54)43(2,3)27-64-71(61,62)68-70(59,60)63-26-32-37(67-69(56,57)58)36(53)42(66-32)50-29-49-35-39(44)47-28-48-40(35)50/h5,7-10,13-17,28-32,36-38,42,53-54H,4,6,11-12,18-27H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58) |
---|
Synonyms | Value | Source |
---|
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-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulfanyl)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-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulphanyl)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-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid | Generator |
|
---|
Chemical Formula | C43H66N7O18P3S |
---|
Average Molecular Weight | 1094.01 |
---|
Monoisotopic Molecular Weight | 1093.339790481 |
---|
IUPAC Name | {[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid |
---|
Traditional Name | [5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-({15-[3-(pent-2-en-1-yl)oxiran-2-yl]pentadeca-4,7,10,13-tetraenoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | CCC=CCC1OC1CC=CCC=CCC=CCC=CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N |
---|
InChI Identifier | InChI=1S/C43H66N7O18P3S/c1-4-5-16-19-30-31(65-30)20-17-14-12-10-8-6-7-9-11-13-15-18-21-34(52)72-25-24-45-33(51)22-23-46-41(55)38(54)43(2,3)27-64-71(61,62)68-70(59,60)63-26-32-37(67-69(56,57)58)36(53)42(66-32)50-29-49-35-39(44)47-28-48-40(35)50/h5,7-10,13-17,28-32,36-38,42,53-54H,4,6,11-12,18-27H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58) |
---|
InChI Key | CCGDDLGKOSNYHP-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Classification | Not classified |
---|
Ontology |
---|
Not Available | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
MS | Mass Spectrum (Electron Ionization) | Not Available | 2022-08-06 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 10V, Positive-QTOF | splash10-0006-9000000000-2dadce16b74684d18bd8 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 20V, Positive-QTOF | splash10-005i-9300000103-d63825485ae996f5fb89 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 40V, Positive-QTOF | splash10-000i-0000490000-2d09b00ea1740a1f3d16 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 10V, Negative-QTOF | splash10-0006-9000000000-1600ee74362d22662d3a | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 20V, Negative-QTOF | splash10-0096-9000100101-f24f6fd74aec929a8681 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl-CoA 40V, Negative-QTOF | splash10-004r-9102400402-d2fa422d70cd0dfcd17b | 2021-10-21 | Wishart Lab | View Spectrum |
|
---|