Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2021-09-14 15:45:05 UTC |
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HMDB ID | HMDB0001064 |
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Secondary Accession Numbers | - HMDB0060170
- HMDB01064
- HMDB60170
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Metabolite Identification |
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Common Name | Linoleoyl-CoA |
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Description | 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 ). |
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Structure | CCCCC\C=C/C\C=C/CCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N InChI=1S/C39H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8-,12-11-/t28-,32-,33-,34+,38-/m1/s1 |
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Synonyms | Value | Source |
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(9Z,12Z)-Octadecadienoyl-CoA | ChEBI | Linoleoyl-coenzyme A | HMDB | Linoleoyl-coenzyme A, (Z,Z)-isomer | HMDB | (Z,Z)-9,12-Octadecadienoyl-CoA | HMDB | CoA(18:2(9Z,12Z)) | HMDB | Linoleic coenzyme A | HMDB | Linoleoyl coenzyme A | HMDB | Linoleyl-CoA | HMDB | Linoleyl-coenzyme A | HMDB | (9Z,12Z)-Octadecadienoyl-coenzyme A | HMDB | Linoleoyl-CoA | HMDB |
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Chemical Formula | C39H66N7O17P3S |
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Average Molecular Weight | 1029.97 |
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Monoisotopic Molecular Weight | 1029.344875861 |
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IUPAC Name | {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid |
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Traditional Name | linoleoyl-coa |
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CAS Registry Number | 6709-57-5 |
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SMILES | CCCCC\C=C/C\C=C/CCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N |
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InChI Identifier | InChI=1S/C39H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8-,12-11-/t28-,32-,33-,34+,38-/m1/s1 |
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InChI Key | YECLLIMZHNYFCK-RRNJGNTNSA-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 3',5'-bisphosphate
- Purine ribonucleoside bisphosphate
- Purine ribonucleoside diphosphate
- Ribonucleoside 3'-phosphate
- Pentose phosphate
- Pentose-5-phosphate
- Beta amino acid or derivatives
- Glycosyl compound
- N-glycosyl compound
- 6-aminopurine
- Monosaccharide phosphate
- Organic pyrophosphate
- Pentose monosaccharide
- Imidazopyrimidine
- Purine
- Monoalkyl phosphate
- Aminopyrimidine
- Imidolactam
- N-acyl-amine
- N-substituted imidazole
- Organic phosphoric acid derivative
- Monosaccharide
- Pyrimidine
- Alkyl phosphate
- Fatty amide
- Phosphoric acid ester
- Tetrahydrofuran
- Imidazole
- Azole
- Heteroaromatic compound
- Carbothioic s-ester
- Secondary alcohol
- Thiocarboxylic acid ester
- Carboxamide group
- Secondary carboxylic acid amide
- Amino acid or derivatives
- Sulfenyl compound
- Thiocarboxylic acid or derivatives
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Carboxylic acid derivative
- Organosulfur compound
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic nitrogen compound
- Primary amine
- Organopnictogen compound
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition
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Biological location
Source
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Process
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Naturally occurring process
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Physical Properties |
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State | Solid |
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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 Kovats Retention IndicesNot Available |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 123V, negative-QTOF | splash10-056r-1100903000-97979bc4426e696ca500 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 133V, negative-QTOF | splash10-0a6r-2211903000-4df18afe923088dccc9d | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 135V, negative-QTOF | splash10-0a6r-2311904000-084368125746db9a1a8d | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 160V, negative-QTOF | splash10-056r-9834804000-ca985ff7e3a0a2cf068c | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 168V, negative-QTOF | splash10-056r-9723402000-1ea9fba94f19b641305d | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 185V, negative-QTOF | splash10-056r-9622100000-4bcd035304dec49a3add | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 199V, negative-QTOF | splash10-004i-9511000000-1f5c4a5c6b6d8b944e54 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 218V, negative-QTOF | splash10-004i-9410000000-cdcfa205f52edfcda7f1 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 232V, negative-QTOF | splash10-004i-9400000000-678749dd033055882657 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 253V, negative-QTOF | splash10-004i-9400000000-dcd823851fb7d4ad77a7 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 273V, negative-QTOF | splash10-004i-9300000000-2e76dfce41f4d4f8fea5 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 304V, negative-QTOF | splash10-004i-9300000000-6a4626bbeafb9da35d70 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA n/a 72V, negative-QTOF | splash10-001i-1000209003-f68430866c04428bfb90 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 47V, positive-QTOF | splash10-001i-9000200000-2cabae93047abe4a748d | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 65V, positive-QTOF | splash10-00fr-3000970000-f399f99de6048f888713 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 100V, positive-QTOF | splash10-00di-0100590000-9dc110d2f0daecf49e4d | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 133V, positive-QTOF | splash10-00dr-1930160000-1caa8491ab78bfd3d5a9 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 168V, positive-QTOF | splash10-000i-2920000000-c8b0b7ed0a3db1633f65 | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA Orbitrap 247V, positive-QTOF | splash10-000i-4900000000-70e58b576b80fd6196af | 2020-07-22 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Linoleoyl-CoA n/a 72V, positive-QTOF | splash10-00di-0000490000-7f3332450575be86b2d1 | 2020-07-22 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Linoleoyl-CoA 10V, Positive-QTOF | splash10-001i-9000000000-08cf5e6d7b995d0cb8cd | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Linoleoyl-CoA 20V, Positive-QTOF | splash10-01p9-7900200548-53d677114eea1a3495ee | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Linoleoyl-CoA 40V, Positive-QTOF | splash10-00di-0200890000-1142d1b46c4936109361 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Linoleoyl-CoA 10V, Negative-QTOF | splash10-004i-9000000000-47a1be0b9f32d430c281 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Linoleoyl-CoA 20V, Negative-QTOF | splash10-004i-9010201300-d0da1a5320d13a306df8 | 2021-09-25 | Wishart Lab | View Spectrum |
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General References | - Ramsay RR, Mancinelli G, Arduini A: Carnitine palmitoyltransferase in human erythrocyte membrane. Properties and malonyl-CoA sensitivity. Biochem J. 1991 May 1;275 ( Pt 3):685-8. [PubMed:2039446 ]
- Domergue F, Abbadi A, Ott C, Zank TK, Zahringer U, Heinz E: Acyl carriers used as substrates by the desaturases and elongases involved in very long-chain polyunsaturated fatty acids biosynthesis reconstituted in yeast. J Biol Chem. 2003 Sep 12;278(37):35115-26. Epub 2003 Jun 30. [PubMed:12835316 ]
- Kawasaki T, Snyder F: Synthesis of a novel acetylated neutral lipid related to platelet-activating factor by acyl-CoA:1-O-alkyl-2-acetyl-sn-glycerol acyltransferase in HL-60 cells. J Biol Chem. 1988 Feb 25;263(6):2593-6. [PubMed:3422635 ]
- Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
- Ensenauer R, He M, Willard JM, Goetzman ES, Corydon TJ, Vandahl BB, Mohsen AW, Isaya G, Vockley J: Human acyl-CoA dehydrogenase-9 plays a novel role in the mitochondrial beta-oxidation of unsaturated fatty acids. J Biol Chem. 2005 Sep 16;280(37):32309-16. Epub 2005 Jul 14. [PubMed:16020546 ]
- Ciapaite J, Bakker SJ, Van Eikenhorst G, Wagner MJ, Teerlink T, Schalkwijk CG, Fodor M, Ouwens DM, Diamant M, Heine RJ, Westerhoff HV, Krab K: Functioning of oxidative phosphorylation in liver mitochondria of high-fat diet fed rats. Biochim Biophys Acta. 2007 Mar;1772(3):307-16. Epub 2006 Nov 10. [PubMed:17184976 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- (). Silva C, Loyola G, Valenzuela R, García-Huidobro T, Monasterio O, Bronfman M. High-affinity binding of fatty acyl-CoAs and peroxisome proliferator-CoA esters to glutathione S-transferases effect on enzymatic activity. Eur J Biochem. 1999 Nov;266(1):143-50.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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