Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:56:08 -0600 |
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Update Date | 2015-06-03 15:54:15 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | (S)-Methylmalonic acid semialdehyde |
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Description | Methylmalonic semialdehyde is a metabolite in valine catabolism, inositol metabolism and propanoate metabolism. Methylmalonate-semialdehyde dehydrogenase (MMSDH) catalyses the NAD+ and coenzyme A-dependent conversion of methylmalonate semialdehyde to propionyl-CoA in the distal region of the L-valine catabolic pathway. Direct enzymatic assay of MMSDH is difficult since the substrate, methylmalonate semialdehyde, is both commercially unavailable and notoriously unstable as a b-keto acid. (PMID: 10947204) |
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Structure | |
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Synonyms: | - (2S)-2-methyl-3-oxopropanoate
- (2S)-2-methyl-3-oxopropanoic acid
- (S)-Methylmalonate semialdehyde
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Chemical Formula: | C4H6O3 |
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Weight: | Average: 102.0886 Monoisotopic: 102.031694058 |
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InChI Key: | VOKUMXABRRXHAR-VKHMYHEASA-N |
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InChI: | InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)/t3-/m0/s1 |
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CAS number: | 99043-16-0 |
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IUPAC Name: | (2S)-2-methyl-3-oxopropanoic acid |
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Traditional IUPAC Name: | (S)-methylmalonaldehydic acid |
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SMILES: | C[C@@H](C=O)C(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | 1,3-dicarbonyl compounds |
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Alternative Parents | |
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Substituents | - 1,3-dicarbonyl compound
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxide
- Hydrocarbon derivative
- Short-chain aldehyde
- Aldehyde
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | -1 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | |
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KEGG Pathways: | - Microbial metabolism in diverse environments ec01120
- Propanoate metabolism ec00640
- Trinitrotoluene degradation ec00633
- Valine, leucine and isoleucine degradation ec00280
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9000000000-8b181508e3ce65539b46 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9600000000-15e42a2e09123d5f22ad | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0zg0-9400000000-e46caa43ec4709ce7686 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9000000000-6c1632ad1d7983990262 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-6762a2cf4db52c84495c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-2900000000-9066dc83487b73946c99 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-9200000000-8fde49823ba2083f055f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-a320f14ddfc09e798938 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0uk9-8900000000-0a76d84228c38b1cfe1d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0pb9-9300000000-dd49ef94a8379e8517cd | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-4f42a2a7dc0b37e742da | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-9000000000-b5c480248a004c069416 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9000000000-6de8f6b91e5efd633c28 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4r-9000000000-a0e9ace5e33e8c50915e | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Chambliss, K. L., Gray, R. G., Rylance, G., Pollitt, R. J., Gibson, K. M. (2000). "Molecular characterization of methylmalonate semialdehyde dehydrogenase deficiency." J Inherit Metab Dis 23:497-504. Pubmed: 10947204
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Manning NJ, Pollitt RJ: Tracer studies of the interconversion of R- and S-methylmalonic semialdehydes in man. Biochem J. 1985 Oct 15;231(2):481-4. Pubmed: 4062908
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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