| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 00:26:35 UTC |
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| Update date | 2015-07-21 06:57:35 UTC |
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| Primary ID | FDB023226 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | 2-Methylacetoacetic acid |
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| Description | 2-Methylacetoacetic acid is a metabolite that has an increased excretion in patients with acetoacetyl-CoA thiolase (EC 2.3.1.9) deficiency (OMIM 607809, ACAT1; OMIM 100678, ACAT2; OMIM 604770, ACAA2; OMIM 607809). Thiolases are ubiquitous and important enzymes. Several isoenzymes are known, which can occur in the cytosol (ACAT2), the mitochondria (ACAT1) , or the peroxisomes(ACAA2).
Thiolases are CoA-dependent enzymes which catalyze the formation of a carbon-carbon bond in a Claisen condensation step and its reverse reaction via a thiolytic degradation mechanism. mitochondrial acetoacetyl-coenzyme A (CoA) thiolase (T2) is important in the pathways for the synthesis and degradation of ketone bodies as well as for the degradation of 2-methylacetoacetyl-CoA. (PMID: 17371050, 14518824, 9744475, 9001814) [HMDB] |
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| CAS Number | 2382-59-4 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C5H8O3 |
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| IUPAC name | 2-methyl-3-oxobutanoic acid |
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| InChI Identifier | InChI=1S/C5H8O3/c1-3(4(2)6)5(7)8/h3H,1-2H3,(H,7,8) |
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| InChI Key | GCXJINGJZAOJHR-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(C(C)=O)C(O)=O |
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| Average Molecular Weight | 116.1152 |
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| Monoisotopic Molecular Weight | 116.047344122 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Keto acids and derivatives |
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| Sub Class | Short-chain keto acids and derivatives |
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| Direct Parent | Short-chain keto acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Beta-keto acid
- Branched fatty acid
- Methyl-branched fatty acid
- Short-chain keto acid
- Beta-hydroxy ketone
- Fatty acyl
- 1,3-dicarbonyl compound
- Ketone
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Carbonyl group
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Organic oxide
- 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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| Role | Biological role: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | 2-Methylacetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9000000000-4522174bd24a6b761d39 | Spectrum | | Predicted GC-MS | 2-Methylacetoacetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00fr-8900000000-fee1d74840bb965bcfe4 | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-9600000000-d0862c2daa04fdcefc78 | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0g6s-9100000000-90a265e5eaa63e5ef5e0 | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pb9-9000000000-661f491ab0f15426947b | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-6900000000-54e32b9b92df94a1fe9e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-e95b19f182cd6fb67e1d | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0l6r-9000000000-82441ad6584e10cb7f43 | 2016-08-03 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 133090 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 150996 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 37079 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB03771 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | |
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