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Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-05-22 14:17:42 UTC |
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Update Date | 2020-06-22 21:24:52 UTC |
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HMDB ID | HMDB0002217 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (S)-Methylmalonic acid semialdehyde |
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Description | (S)-Methylmalonic acid semialdehyde, also known as (2S)-2-methyl-3-oxopropanoate, 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 (S)-Methylmalonic acid semialdehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-Methylmalonic acid semialdehyde exists in all living organisms, ranging from bacteria to humans. Within humans, (S)-methylmalonic acid semialdehyde participates in a number of enzymatic reactions. In particular, (S)-methylmalonic acid semialdehyde can be biosynthesized from (S)-3-hydroxyisobutyric acid; which is catalyzed by the enzymes 3-hydroxyisobutyrate dehydrogenase, mitochondrial and enoyl-CoA hydratase, mitochondrial. In addition, (S)-methylmalonic acid semialdehyde and L-glutamic acid can be biosynthesized from (S)-beta-aminoisobutyric acid and oxoglutaric acid; which is catalyzed by the enzyme 4-aminobutyrate aminotransferase, mitochondrial. In humans, (S)-methylmalonic acid semialdehyde is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. 2-Methyl-3-oxopropanoic acid with configuration S at the chiral centre. |
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Structure | |
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Synonyms | Value | Source |
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(S)-Methylmalonate semialdehyde | ChEBI | (2S)-2-Methyl-3-oxopropanoate | HMDB | (2S)-2-Methyl-3-oxopropanoic acid | HMDB |
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Chemical Formula | C4H6O3 |
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Average Molecular Weight | 102.0886 |
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Monoisotopic Molecular Weight | 102.031694058 |
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IUPAC Name | (2S)-2-methyl-3-oxopropanoic acid |
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Traditional Name | (S)-methylmalonaldehydic acid |
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CAS Registry Number | 99043-16-0 |
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SMILES | C[C@@H](C=O)C(O)=O |
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InChI Identifier | InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)/t3-/m0/s1 |
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InChI Key | VOKUMXABRRXHAR-VKHMYHEASA-N |
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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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Ontology |
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Disposition | Source: |
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Process | Naturally occurring process: |
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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9000000000-8b181508e3ce65539b46 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9600000000-15e42a2e09123d5f22ad | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0zg0-9400000000-e46caa43ec4709ce7686 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-9000000000-6c1632ad1d7983990262 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-6762a2cf4db52c84495c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-2900000000-9066dc83487b73946c99 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-9200000000-8fde49823ba2083f055f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-a320f14ddfc09e798938 | Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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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 | FDB022912 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4575365 |
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KEGG Compound ID | C06002 |
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BioCyc ID | CH3-MALONATE-S-ALD |
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BiGG ID | 34698 |
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Wikipedia Link | Not Available |
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METLIN ID | 6553 |
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PubChem Compound | 5462303 |
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PDB ID | Not Available |
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ChEBI ID | 27821 |
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Food Biomarker Ontology | Not Available |
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VMH ID | MMTSA |
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MarkerDB ID | |
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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 | - 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 ]
- Chambliss KL, Gray RG, Rylance G, Pollitt RJ, Gibson KM: Molecular characterization of methylmalonate semialdehyde dehydrogenase deficiency. J Inherit Metab Dis. 2000 Jul;23(5):497-504. [PubMed:10947204 ]
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