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 | 2022-03-07 02:49:08 UTC |
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HMDB ID | HMDB0001041 |
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Secondary Accession Numbers | - HMDB0002021
- HMDB0002191
- HMDB0002253
- HMDB0060317
- HMDB01041
- HMDB02021
- HMDB02191
- HMDB02253
- HMDB60317
| Show more accession numbers
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Metabolite Identification |
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Common Name | 2-Methylbutyryl-CoA |
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Description | 2-Methylbutyryl-CoA (CAS: 6712-02-3), also known as alpha-methylbutyryl-coenzyme A, belongs to the class of organic compounds known as acyl-CoAs. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. 2-Methylbutyryl-CoA is a strong basic compound (based on its pKa). 2-Methylbutyryl-CoA is a product of isoleucine catabolism. It is converted into tiglyl-CoA by short/branched-chain acyl-CoA dehydrogenase. 2-Methylbutyryl-CoA dehydrogenase deficiency, also known as 2-methyl-3-hydroxybutyryl-CoA dehydrogenase deficiency or MBHD, is an inherited disorder in which the body is unable to process the amino acid isoleucine properly. It is caused by a mutation in the HADH2 gene. Untreated MBHD can lead to progressive loss of motor skills, mental retardation, and epilepsy. |
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Structure | CC[C@H](C)C(=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/C26H44N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h12-15,18-20,24,35-36H,5-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t14-,15+,18+,19+,20-,24+/m0/s1 |
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Synonyms | Value | Source |
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(S)-2-Methylbutanoyl-coenzyme A | ChEBI | (S)-2-Methylbutyryl-CoA | ChEBI | (S)-2-Methylbutyryl-coenzyme A | ChEBI | 2-Methylbutyryl CoA | HMDB | 2-Methylbutyryl-CoA | HMDB | 2-Methylbutyryl-coenzyme A | HMDB | alpha-Methylbutyryl CoA | HMDB | alpha-Methylbutyryl coenzyme A | HMDB | α-Methylbutyryl CoA | HMDB | α-Methylbutyryl 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[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(2S)-2-methylbutanoyl]sulfanyl}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((3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(2S)-2-methylbutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid |
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CAS Registry Number | 87069-91-8 |
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SMILES | CC[C@H](C)C(=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/C26H44N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h12-15,18-20,24,35-36H,5-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t14-,15+,18+,19+,20-,24+/m0/s1 |
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InChI Key | LYNVNYDEQMMNMZ-JRQZLUQRSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an 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 | 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 | Not Available |
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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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| GC-MS SpectraSpectrum 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 SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 10V, Positive-QTOF | splash10-01q0-1931000110-ab791f11c73f2215c6b0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 20V, Positive-QTOF | splash10-01p9-1911000000-6e94251b557f9c232a8b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 40V, Positive-QTOF | splash10-01p9-2920000000-787d830b8ce5a58a9fc3 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 10V, Negative-QTOF | splash10-001i-9830142650-5daf6d2ebf4706addb66 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 20V, Negative-QTOF | splash10-001i-5910010010-82942ef01fc9c3168a0a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 40V, Negative-QTOF | splash10-057i-5900100000-862949faa1b8743f72e7 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 10V, Negative-QTOF | splash10-0udi-0000000090-31b6c89b394831637a8f | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 20V, Negative-QTOF | splash10-0gc9-9800102240-781ca81e401e13a0c8b5 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 40V, Negative-QTOF | splash10-00p0-4003603910-d8729ca53079a09ed285 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 10V, Positive-QTOF | splash10-0udi-0000000190-7fb257dc3645f69b632d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 20V, Positive-QTOF | splash10-000i-1910002340-4c7d3d3d8e594fa50ebf | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Methylbutyryl-CoA 40V, Positive-QTOF | splash10-0002-0029000000-b2613cd6598aaa60f225 | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane
- Mitochondria
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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 | FDB022387 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 30791986 |
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KEGG Compound ID | C15980 |
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BioCyc ID | 2-METHYL-BUTYRYL-COA |
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BiGG ID | Not Available |
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Wikipedia Link | 2-Methylbutyryl-CoA |
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METLIN ID | Not Available |
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PubChem Compound | 71448903 |
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PDB ID | Not Available |
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ChEBI ID | 90222 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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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 | - Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
- 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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