Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-07-25 00:12:05 UTC |
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Update Date | 2022-03-07 02:51:28 UTC |
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HMDB ID | HMDB0013037 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Pentanoyl-CoA |
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Description | Pentanoyl CoA is an acyl-CoA with the C-5 Acyl chain. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine. |
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Structure | CCCCC(=O)SCCNC(=O)CCNC(=O)C(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/C26H44N7O17P3S/c1-4-5-6-17(35)54-10-9-28-16(34)7-8-29-24(38)21(37)26(2,3)12-47-53(44,45)50-52(42,43)46-11-15-20(49-51(39,40)41)19(36)25(48-15)33-14-32-18-22(27)30-13-31-23(18)33/h13-15,19-21,25,36-37H,4-12H2,1-3H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1 |
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Synonyms | Value | Source |
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Pentanoyl-coenzyme A | HMDB |
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Chemical Formula | C26H44N7O17P3S |
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Average Molecular Weight | 851.651 |
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Monoisotopic Molecular Weight | 851.172723243 |
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IUPAC Name | {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(pentanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid |
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Traditional Name | [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(pentanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCC(=O)SCCNC(=O)CCNC(=O)C(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/C26H44N7O17P3S/c1-4-5-6-17(35)54-10-9-28-16(34)7-8-29-24(38)21(37)26(2,3)12-47-53(44,45)50-52(42,43)46-11-15-20(49-51(39,40)41)19(36)25(48-15)33-14-32-18-22(27)30-13-31-23(18)33/h13-15,19-21,25,36-37H,4-12H2,1-3H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1 |
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InChI Key | RXUATCUKICAIOA-TVCSPYKZSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. |
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Kingdom | Inorganic compounds |
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Super Class | Homogeneous metal compounds |
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Class | Homogeneous transition metal compounds |
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Sub Class | Not Available |
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Direct Parent | Homogeneous transition metal compounds |
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Alternative Parents | Not Available |
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Substituents | - Homogeneous transition metal
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Molecular Framework | Not Available |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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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 | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized | Show more...
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Spectra |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 10V, Positive-QTOF | splash10-000i-2901000120-2a423c1bd81049be2f37 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 20V, Positive-QTOF | splash10-000i-1913000000-a7882da7f4659358dd99 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 40V, Positive-QTOF | splash10-000i-1911000000-dd4d2426d295e6cea710 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 10V, Negative-QTOF | splash10-001i-7930140450-c93bb9584e9108db8543 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 20V, Negative-QTOF | splash10-001i-6910010000-390528f5d6ef7539cb68 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 40V, Negative-QTOF | splash10-057i-5900100000-f9c4115d1b808c86f8f7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 10V, Positive-QTOF | splash10-0udi-0000000090-3758b512fc2398854707 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 20V, Positive-QTOF | splash10-000i-0900001560-656412ccb7e988988a2b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 40V, Positive-QTOF | splash10-0002-0029000000-298400882ff5c02d176c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 10V, Negative-QTOF | splash10-0udi-0000000090-c1d8a32a3fcbde2b3b71 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 20V, Negative-QTOF | splash10-0fas-9200202360-645cab450d162098ff13 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pentanoyl-CoA 40V, Negative-QTOF | splash10-00p0-6204702920-60948d54a96619a917a8 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
| Show more...
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB029262 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 388465 |
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KEGG Compound ID | C00888 |
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BioCyc ID | 5-HYDROXYPENTANOYL-COA |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 439337 |
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PDB ID | Not Available |
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ChEBI ID | 15536 |
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Food Biomarker Ontology | Not Available |
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VMH ID | M02694 |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - 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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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