Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:55:25 -0600 |
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Update Date | 2015-06-03 15:54:14 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | 4-Hydroxy-2-oxoglutaric acid |
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Description | 4-hydroxy-2-oxoglutaric acid 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. 4-hydroxy-2-oxoglutaric acid is invovled in Glyoxylate and dicarboxylate metabolism. 2-Keto-4-hydroxyglutarate aldolase also plays a role in respiratory metabolic pathways, which suggests a mechanism for respiration resumption during the termination of the SOS response. (PMID 8524853) |
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Structure | |
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Synonyms: | - (+/-)-2-hydroxy-4-oxopentanedioate
- (+/-)-2-hydroxy-4-oxopentanedioic acid
- 2-Hydroxy-4-oxopentanedioate
- 2-Hydroxy-4-oxopentanedioic acid
- 2-k-4-OH-glutarate
- 2-k-4-OH-glutaric acid
- 2-Keto-4-hydroxyglutarate
- 2-Keto-4-hydroxyglutaric acid
- 2-Oxo-4-hydroxyglutarate
- 2-Oxo-4-hydroxyglutaric acid
- 4-Hydroxy-2-ketoglutarate
- 4-Hydroxy-2-ketoglutaric acid
- 4-Hydroxy-2-oxoglutarate
- 4-Hydroxy-2-oxoglutaric acid
- D-4-HYDROXY-2-KETO-GLUTARATE
- D-4-HYDROXY-2-keto-glutaric acid
- D-4-Hydroxy-2-ketoglutarate
- D-4-Hydroxy-2-ketoglutaric acid
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Chemical Formula: | C5H6O6 |
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Weight: | Average: 162.0975 Monoisotopic: 162.016437924 |
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InChI Key: | WXSKVKPSMAHCSG-UHFFFAOYSA-N |
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InChI: | InChI=1S/C5H6O6/c6-2(4(8)9)1-3(7)5(10)11/h2,6H,1H2,(H,8,9)(H,10,11) |
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CAS number: | Not Available |
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IUPAC Name: | 2-hydroxy-4-oxopentanedioic acid |
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Traditional IUPAC Name: | 4-hydroxy-2-oxoglutaric acid |
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SMILES: | OC(CC(=O)C(O)=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
- Alpha-hydroxy acid
- Alpha-keto acid
- Beta-hydroxy ketone
- Dicarboxylic acid or derivatives
- Hydroxy acid
- Alpha-hydroxy ketone
- Secondary alcohol
- Ketone
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Organic oxygen compound
- 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: | Not Available |
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KEGG Pathways: | - Arginine and proline metabolism ec00330
- Glyoxylate and dicarboxylate metabolism ec00630
- Metabolic pathways eco01100
- Pentose phosphate pathway ec00030
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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 | splash10-006x-9100000000-86646efd7b91f9c2b26e | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-03ki-5194000000-f0675d41da8301324b83 | 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 | splash10-01ot-2900000000-fd2a634c0c83321df9f8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002b-6900000000-13f2fbc268a7b1bfe885 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05i4-9100000000-ca03fcf215517c709245 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-2900000000-7b0bd810c920b58daa79 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00xs-9600000000-6734be382dda3c66592a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00dm-9000000000-ff1b08ca89e9629f0912 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kb-6900000000-661f455fd4b6e8da0c82 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dm-9100000000-b9bce861b26dd8001332 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-a0587223ecf12202531f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014j-5900000000-30fe0301167b3cea2c0b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-006t-9000000000-5bbf6f8b15e9a3af889b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-e7768f77ba36e7e3743b | View in MoNA |
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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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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Cayrol, C., Petit, C., Raynaud, B., Capdevielle, J., Guillemot, J. C., Defais, M. (1995). "Recovery of respiration following the SOS response of Escherichia coli requires RecA-mediated induction of 2-keto-4-hydroxyglutarate aldolase." Proc Natl Acad Sci U S A 92:11806-11809. Pubmed: 8524853
- 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
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- 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) | Not Available |
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Links |
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External Links: | |
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