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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:26:43 UTC |
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Update Date | 2020-06-04 20:52:18 UTC |
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BMDB ID | BMDB0000208 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Oxoglutaric acid |
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Description | Oxoglutaric acid, also known as oxoglutarate or alpha-ketoglutarate, 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. Oxoglutaric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Oxoglutaric acid exists in all living species, ranging from bacteria to humans. Oxoglutaric acid is a potentially toxic compound. Oxoglutaric acid has been found to be associated with several diseases known as schizophrenia, eosinophilic esophagitis, amish lethal microcephaly, and anoxia; also oxoglutaric acid has been linked to the inborn metabolic disorders including d-2-hydroxyglutaric aciduria. |
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Structure | |
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Synonyms | Value | Source |
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2-Ketoglutaric acid | ChEBI | alpha-Ketoglutaric acid | ChEBI | 2-Ketoglutarate | Generator | a-Ketoglutarate | Generator | a-Ketoglutaric acid | Generator | alpha-Ketoglutarate | Generator | Α-ketoglutarate | Generator | Α-ketoglutaric acid | Generator | Oxoglutarate | Generator | 2-oxo-1,5-Pentanedioate | HMDB | 2-oxo-1,5-Pentanedioic acid | HMDB | 2-Oxoglutarate | HMDB | 2-Oxoglutaric acid | HMDB | 2-Oxopentanedioate | HMDB | 2-Oxopentanedioic acid | HMDB | alpha-Oxoglutarate | HMDB | Oxogluric acid | HMDB | 2 Oxoglutaric acid | HMDB | Ketoglutaric acid | HMDB | alpha Ketoglutaric acid | HMDB | 2 Ketoglutaric acid | HMDB | alpha Ketoglutarate | HMDB | alpha Oxoglutarate | HMDB | 2 Ketoglutarate | HMDB | 2 Oxoglutarate | HMDB | alpha-Oxoglutaric acid | HMDB | alpha-Oxopentanedioic acid | HMDB | alpha-Keto-glutaric acid | HMDB | Α-oxoglutaric acid | HMDB | Α-oxopentanedioic acid | HMDB | Α-keto-glutaric acid | HMDB |
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Chemical Formula | C5H6O5 |
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Average Molecular Weight | 146.0981 |
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Monoisotopic Molecular Weight | 146.021523302 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 328-50-7 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10) |
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InChI Key | KPGXRSRHYNQIFN-UHFFFAOYSA-N |
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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
- Alpha-hydroxy ketone
- Ketone
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Cytoplasm
- Endoplasmic reticulum
- Mitochondria
- Peroxisome
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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 | 115.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 541.5 mg/mL | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
- Mitochondria
- Peroxisome
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Biospecimen Locations | - Blood
- Mammary Gland
- Milk
- Placenta
- Ruminal Fluid
- Semen
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Pathways | |
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Normal Concentrations |
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Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 117.93 +/- 17.22 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 104 +/- 7 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 277.1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 112 +/- 7 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 103 +/- 3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 109 +/- 6 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 37 - 156 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 70 - 156 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 240 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 90 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 102 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 116.48 +/- 18.59 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 111.39 +/- 15.62 uM | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 40 +/- 24 uM | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details |
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External Links |
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HMDB ID | HMDB0000208 |
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DrugBank ID | DB08845 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB003361 |
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KNApSAcK ID | C00000769 |
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Chemspider ID | 50 |
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KEGG Compound ID | C00026 |
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BioCyc ID | 2-KETOGLUTARATE |
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BiGG ID | 33565 |
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Wikipedia Link | Alpha-Ketoglutaric_acid |
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METLIN ID | 5218 |
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PubChem Compound | 51 |
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PDB ID | Not Available |
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ChEBI ID | 30915 |
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References |
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Synthesis Reference | Tanaka, Katsunobu; kimura, Kazu; Yamaguchi, Ken. Fermentative production of a-oxoglutaric acid. U.S. (1973), 4 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83. [PubMed:2760296 ]
- Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6. [PubMed:9891269 ]
- Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2. [PubMed:11132867 ]
- Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
- Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
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