Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-13 09:40:14 UTC |
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Update Date | 2022-03-07 02:49:20 UTC |
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HMDB ID | HMDB0004047 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Adipoyl-CoA |
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Description | Adipoyl-CoA is formed as the degradation beta-oxidation product (CoA ester) of the dicarboxylic acid formed via w-oxidation of fatty acids in the endoplasmic reticulum. Fatty acid oxidation is an important source of energy, especially during fasting and diabetes. Although mitochondria are considered the primary site for beta-oxidation of fatty acids for energy utilization, peroxisomes play a key role in the metabolism of a variety of lipids such as very long-chain fatty acids, branched-chain fatty acids, dicarboxylic fatty acids, bile acid intermediates, prostaglandins, leukotrienes, thromboxanes, pristanic acid, and xenobiotic carboxylic acids. Acyl-CoA thioesterases (ACOTs) are a family of enzymes that catalyze the hydrolysis of the CoA esters of various lipids to the free acids and coenzyme A. Acyl-CoA hydrolase 8 (ACOT8, EC 3.1.2.20) preferentially hydrolyzes medium-chain dicarboxylyl-CoA esters such as Adipoyl-CoA and is responsible for the termination of beta-oxidation of dicarboxylic acids of medium-chain length with the concomitant release of the corresponding free acids. In mitochondria, Adipoyl-CoA is a substrate of the enzyme Hydroxymethylglutarate coenzyme A-transferase (E.C. 2.8.3.13). Both synthesis and degradation of dicarboxylic acids occur mainly in kidney and liver, and the chain-shortened dicarboxylic acids are excreted in the urine as the free acids. (PMID: 16141203 ). |
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Structure | CC(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)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCC(O)=O InChI=1S/C27H44N7O19P3S/c1-27(2,22(40)25(41)30-8-7-16(35)29-9-10-57-18(38)6-4-3-5-17(36)37)12-50-56(47,48)53-55(45,46)49-11-15-21(52-54(42,43)44)20(39)26(51-15)34-14-33-19-23(28)31-13-32-24(19)34/h13-15,20-22,26,39-40H,3-12H2,1-2H3,(H,29,35)(H,30,41)(H,36,37)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)/t15-,20-,21-,22+,26-/m1/s1 |
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Synonyms | Value | Source |
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5-Carboxypentanoyl-CoA | ChEBI | 5-Carboxypentanoyl-coenzyme A | ChEBI | Adipoyl-coenzyme A | ChEBI | Adipyl-CoA | ChEBI | S-(Hydrogen hexanedioate | HMDB | S-(Hydrogen hexanedioate)CoA | HMDB | S-(Hydrogen hexanedioate)coenzyme A | HMDB | S-(Hydrogen hexanedioic acid | HMDB |
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Chemical Formula | C27H44N7O19P3S |
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Average Molecular Weight | 895.66 |
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Monoisotopic Molecular Weight | 895.162552487 |
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IUPAC Name | 6-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-6-oxohexanoic acid |
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Traditional Name | Adipyl-CoA |
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CAS Registry Number | 25119-42-0 |
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SMILES | CC(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)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCC(O)=O |
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InChI Identifier | InChI=1S/C27H44N7O19P3S/c1-27(2,22(40)25(41)30-8-7-16(35)29-9-10-57-18(38)6-4-3-5-17(36)37)12-50-56(47,48)53-55(45,46)49-11-15-21(52-54(42,43)44)20(39)26(51-15)34-14-33-19-23(28)31-13-32-24(19)34/h13-15,20-22,26,39-40H,3-12H2,1-2H3,(H,29,35)(H,30,41)(H,36,37)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)/t15-,20-,21-,22+,26-/m1/s1 |
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InChI Key | SPNAEHGLBRRCGL-BIEWRJSYSA-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 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
- Medium-chain fatty acid
- Monoalkyl phosphate
- Hydroxy fatty acid
- Aminopyrimidine
- Thia fatty acid
- Fatty acid
- Imidolactam
- Pyrimidine
- Alkyl phosphate
- Organic phosphoric acid derivative
- N-substituted imidazole
- Phosphoric acid ester
- Monosaccharide
- N-acyl-amine
- Fatty amide
- Tetrahydrofuran
- Heteroaromatic compound
- Azole
- Imidazole
- Amino acid
- Carboxamide group
- Amino acid or derivatives
- Carbothioic s-ester
- Secondary alcohol
- Thiocarboxylic acid ester
- Secondary carboxylic acid amide
- Sulfenyl compound
- Organoheterocyclic compound
- Thiocarboxylic acid or derivatives
- Azacycle
- Oxacycle
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Primary amine
- Hydrocarbon derivative
- Carbonyl group
- Organosulfur compound
- Organopnictogen compound
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Amine
- Organic nitrogen compound
- Alcohol
- 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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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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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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 - Adipoyl-CoA 10V, Positive-QTOF | splash10-000i-1922000140-31343067a4e9118e4335 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adipoyl-CoA 20V, Positive-QTOF | splash10-000i-0934000000-5f1d4e6ae2c1f0f3fe85 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adipoyl-CoA 40V, Positive-QTOF | splash10-000i-1911000000-a759192bd025729ffa86 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adipoyl-CoA 10V, Negative-QTOF | splash10-0059-2911030350-f84308fa1f08a239be7a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adipoyl-CoA 20V, Negative-QTOF | splash10-0059-3911020010-bdb466e26047e6ae2ee3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adipoyl-CoA 40V, Negative-QTOF | splash10-057i-5900100000-ea92819c02d87f09af0e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adipoyl-CoA 10V, Negative-QTOF | splash10-0006-0000000090-29bba0ef41fc8cb2c368 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adipoyl-CoA 20V, Negative-QTOF | splash10-002f-4800000390-258183f1a465d6c1b251 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adipoyl-CoA 40V, Negative-QTOF | splash10-002b-6202310920-1a8b767762f31cbf5978 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adipoyl-CoA 10V, Positive-QTOF | splash10-004s-0200000090-159e3b8b6b9c7bdfa981 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adipoyl-CoA 20V, Positive-QTOF | splash10-01p9-0901000170-e512b9331b16f7e461c7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adipoyl-CoA 40V, Positive-QTOF | splash10-000i-0119000000-b0c0ec293f8accc8dc52 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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