| Record Information |
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| Version | 5.0 |
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| Status | Predicted |
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| Creation Date | 2021-09-22 00:59:54 UTC |
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| Update Date | 2021-10-01 16:55:00 UTC |
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| HMDB ID | HMDB0301558 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA |
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| Description | (4z,7z,10s,11e)-10-hydroperoxy-12-[(1r,4s,5s,6r)-6-[(2z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a (4Z_7Z_10S_11E)-10-hydroperoxy-12-[(1R_4S_5S_6R)-6-[(2Z)-pent-2-en-1-yl]-2_3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4_7_11-trienoic acid thioester of coenzyme A. (4z,7z,10s,11e)-10-hydroperoxy-12-[(1r,4s,5s,6r)-6-[(2z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-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,10s,11e)-10-hydroperoxy-12-[(1r,4s,5s,6r)-6-[(2z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-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,10s,11e)-10-hydroperoxy-12-[(1r,4s,5s,6r)-6-[(2z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-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,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA into (4Z_7Z_10S_11E)-10-hydroperoxy-12-[(1R_4S_5S_6R)-6-[(2Z)-pent-2-en-1-yl]-2_3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4_7_11-trienoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, (4Z_7Z_10S_11E)-10-hydroperoxy-12-[(1R_4S_5S_6R)-6-[(2Z)-pent-2-en-1-yl]-2_3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4_7_11-trienoylcarnitine is converted back to (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA occurs in four steps. First, since (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-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,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-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,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-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 | CCC=CCC1C2CC(OO2)C1C=CC(CC=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)OO InChI=1S/C43H66N7O21P3S/c1-4-5-10-14-28-29(31-22-30(28)68-69-31)17-16-27(67-56)13-11-8-6-7-9-12-15-34(52)75-21-20-45-33(51)18-19-46-41(55)38(54)43(2,3)24-65-74(62,63)71-73(60,61)64-23-32-37(70-72(57,58)59)36(53)42(66-32)50-26-49-35-39(44)47-25-48-40(35)50/h5,7-11,16-17,25-32,36-38,42,53-54,56H,4,6,12-15,18-24H2,1-3H3,(H,45,51)(H,46,55)(H,60,61)(H,62,63)(H2,44,47,48)(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)-N-(2-{[2-({10-hydroperoxy-12-[6-(pent-2-en-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-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)-N-(2-{[2-({10-hydroperoxy-12-[6-(pent-2-en-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-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)-N-(2-{[2-({10-hydroperoxy-12-[6-(pent-2-en-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid | HMDB |
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| Chemical Formula | C43H66N7O21P3S |
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| Average Molecular Weight | 1142.01 |
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| Monoisotopic Molecular Weight | 1141.324534341 |
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| IUPAC Name | {[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-({10-hydroperoxy-12-[6-(pent-2-en-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid |
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| Traditional Name | [5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-({10-hydroperoxy-12-[6-(pent-2-en-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid |
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| CAS Registry Number | Not Available |
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| SMILES | CCC=CCC1C2CC(OO2)C1C=CC(CC=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)OO |
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| InChI Identifier | InChI=1S/C43H66N7O21P3S/c1-4-5-10-14-28-29(31-22-30(28)68-69-31)17-16-27(67-56)13-11-8-6-7-9-12-15-34(52)75-21-20-45-33(51)18-19-46-41(55)38(54)43(2,3)24-65-74(62,63)71-73(60,61)64-23-32-37(70-72(57,58)59)36(53)42(66-32)50-26-49-35-39(44)47-25-48-40(35)50/h5,7-11,16-17,25-32,36-38,42,53-54,56H,4,6,12-15,18-24H2,1-3H3,(H,45,51)(H,46,55)(H,60,61)(H,62,63)(H2,44,47,48)(H2,57,58,59) |
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| InChI Key | KIQMIQWSAJFPPA-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. |
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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 | 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
- Prostaglandin skeleton
- Eicosanoid
- 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
- Ortho-dioxane
- Allylic hydroperoxide
- Heteroaromatic compound
- Tetrahydrofuran
- Imidazole
- Azole
- Ortho-dioxolane
- Dialkyl peroxide
- Carbothioic s-ester
- Thiocarboxylic acid ester
- Secondary carboxylic acid amide
- Secondary alcohol
- Hydroperoxide
- Carboxamide group
- Amino acid or derivatives
- Alkyl hydroperoxide
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Sulfenyl compound
- Thiocarboxylic acid or derivatives
- Peroxol
- 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 | |
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Predicted by Siyang on May 30, 2022 | 15.4559 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 6.22 minutes | 32390414 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 2941.4 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 158.2 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 174.2 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 186.6 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 149.1 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 538.1 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 521.8 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 982.8 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 1102.7 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 655.0 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 998.1 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 415.8 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 309.7 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 488.5 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 249.8 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 14.3 seconds | 40023050 |
Predicted Kovats Retention IndicesNot Available |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| MS | Mass Spectrum (Electron Ionization) | Not Available | 2022-08-06 | Not Available | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA 10V, Positive-QTOF | splash10-0006-1900000000-f404c03640188315bed8 | 2021-10-21 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA 20V, Positive-QTOF | splash10-000f-4900000102-46064624e1ece0a9450c | 2021-10-21 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA 40V, Positive-QTOF | splash10-000i-0000109000-e453ad33fa49f9202ec2 | 2021-10-21 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA 10V, Negative-QTOF | splash10-0a4i-2900000000-678d509ac801e62930d0 | 2021-10-21 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA 20V, Negative-QTOF | splash10-0a6r-9702100100-28c4f79685c7212b171f | 2021-10-21 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (4Z,7Z,10S,11E)-10-hydroperoxy-12-[(1R,4S,5S,6R)-6-[(2Z)-pent-2-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]dodeca-4,7,11-trienoyl-CoA 40V, Negative-QTOF | splash10-00ou-8603601916-0df2b4002727f0c69241 | 2021-10-21 | Wishart Lab | View Spectrum |
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