Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:57:08 -0600 |
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Update Date | 2015-09-13 12:56:12 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | alpha-Ketoglutarate |
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Description | Alpha-ketoglutarate is a member of the chemical class known as Gamma Keto-Acids and Derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Alpha-ketoglutarate is invovled in pentose and glucuronate interconversions, C5-Branched dibasic acid metabolism, Vitamin B6 metabolism, alanine, aspartate and glutamate metabolism, Butanoate metabolism, Glyoxylate and dicarboxylate metabolism, Carbon fixation pathways in prokaryotes, Lysine biosynthesis, Biosynthesis of terpenoids and steroids, and the Citrate cycle (TCA cycle). Alpha-Ketoglutaric acid is one of two ketone derivatives of glutaric acid. (The term ketoglutaric acid, when not further qualified, almost always refers to the alpha variant. Alpha-Ketoglutaric acid varies only by the position of the ketone functional group, and is much less common. Its anion, alpha-ketoglutarate (alpha-KG, also called oxo-glutarate) is an important biological compound. It is the keto acid produced by de-amination of glutamate, and is an intermediate in the Krebs cycle. (WikiPedia) |
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Structure | |
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Synonyms: | - 2-Ketoglutarate
- 2-Ketoglutaric acid
- 2-OG
- 2-Oxo-1,5-pentanedioate
- 2-Oxo-1,5-pentanedioic acid
- 2-Oxoglutarate
- 2-Oxoglutarate(2-)
- 2-Oxoglutaric acid
- 2-Oxoglutaric acid(2-)
- 2-Oxopentanedioate
- 2-Oxopentanedioate, ion(2-)
- 2-Oxopentanedioic acid
- 2-Oxopentanedioic acid, ion(2-)
- a-Ketoglutarate
- a-Ketoglutaric acid
- Alpha-Ketoglutarate
- Alpha-Ketoglutaric acid
- Oxoglutarate
- Oxoglutaric acid
- Pentanedioate, 2-oxo-, ion(2-)
- Pentanedioic acid, 2-oxo-, ion(2-)
- α-Ketoglutarate
- α-Ketoglutaric acid
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Chemical Formula: | C5H4O5 |
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Weight: | Average: 144.0823 Monoisotopic: 144.005873238 |
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InChI Key: | KPGXRSRHYNQIFN-UHFFFAOYSA-L |
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InChI: | InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/p-2 |
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CAS number: | Not Available |
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IUPAC Name: | 2-oxopentanedioate |
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Traditional IUPAC Name: | α ketoglutarate |
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SMILES: | [O-]C(=O)CCC(=O)C([O-])=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. |
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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 | Gamma-keto acids and derivatives |
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Direct Parent | Gamma-keto acids and derivatives |
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Alternative Parents | |
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Substituents | - Gamma-keto acid
- Short-chain keto acid
- Dicarboxylic acid or derivatives
- Alpha-keto acid
- Ketone
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Organic anion
- 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: | Not Available |
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Charge: | -2 |
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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: | - Alanine, aspartate and glutamate metabolism ec00250
- Amino sugar and nucleotide sugar metabolism ec00520
- Arginine and proline metabolism ec00330
- Ascorbate and aldarate metabolism ec00053
- Butanoate metabolism ec00650
- C5-Branched dibasic acid metabolism ec00660
- Carbon fixation in photosynthetic organisms ec00710
- Citrate cycle (TCA cycle) ec00020
- Cysteine and methionine metabolism ec00270
- D-Glutamine and D-glutamate metabolism ec00471
- Glucosinolate biosynthesis ec00966
- Glutathione metabolism ec00480
- Glycine, serine and threonine metabolism ec00260
- Glyoxylate and dicarboxylate metabolism ec00630
- Histidine metabolism ec00340
- Isoquinoline alkaloid biosynthesis ec00950
- Lysine biosynthesis ec00300
- Lysine degradation ec00310
- Metabolic pathways eco01100
- Methane metabolism ec00680
- Microbial metabolism in diverse environments ec01120
- Nitrogen metabolism ec00910
- Novobiocin biosynthesis ec00401
- Pantothenate and CoA biosynthesis ec00770
- Pentose and glucuronate interconversions ec00040
- Phenylalanine metabolism ec00360
- Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
- Propanoate metabolism ec00640
- Reductive carboxylate cycle (CO2 fixation) ec00720
- Sulfur metabolism ec00920
- Taurine and hypotaurine metabolism ec00430
- Tropane, piperidine and pyridine alkaloid biosynthesis ec00960
- Tryptophan metabolism ec00380
- Tyrosine metabolism ec00350
- Ubiquinone and other terpenoid-quinone biosynthesis ec00130
- Valine, leucine and isoleucine biosynthesis ec00290
- Valine, leucine and isoleucine degradation ec00280
- Vitamin B6 metabolism ec00750
- beta-Alanine metabolism ec00410
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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: | |
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References |
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References: | - 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
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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