| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:27:17 UTC |
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| Update Date | 2020-06-04 20:48:59 UTC |
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| BMDB ID | BMDB0000243 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Pyruvic acid |
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| Description | Pyruvic acid, also known as pyroracemic acid or 2-oxopropanoate, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Pyruvic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Pyruvic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Pyruvic acid exists in all living species, ranging from bacteria to humans. Pyruvic acid is a potentially toxic compound. Pyruvic acid has been found to be associated with several diseases known as leigh's syndrome, subacute necrotizing encephalopathy, sne, myopathy with lactic acidosis, hereditary, and 3-hydroxy-3-methylglutaryl-coa synthase deficiency; also pyruvic acid has been linked to several inborn metabolic disorders including 3-methylglutaconic aciduria type ii, x-linked and glucagon deficiency. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2-Ketopropionic acid | ChEBI | | 2-Oxopropanoic acid | ChEBI | | 2-Oxopropansaeure | ChEBI | | 2-Oxopropionsaeure | ChEBI | | Acetylformic acid | ChEBI | | Acide pyruvique | ChEBI | | alpha-Ketopropionic acid | ChEBI | | alpha-Oxopropionsaeure | ChEBI | | Brenztraubensaeure | ChEBI | | BTS | ChEBI | | CH3COCOOH | ChEBI | | Pyroracemic acid | ChEBI | | 2-Oxopropanoate | Kegg | | 2-Ketopropionate | Generator | | Acetylformate | Generator | | a-Ketopropionate | Generator | | a-Ketopropionic acid | Generator | | alpha-Ketopropionate | Generator | | Α-ketopropionate | Generator | | Α-ketopropionic acid | Generator | | a-Oxopropionsaeure | Generator | | Α-oxopropionsaeure | Generator | | Pyroracemate | Generator | | Pyruvate | Generator | | 2-Oxopropionate | HMDB | | 2-Oxopropionic acid | HMDB | | Acid, pyruvic | MeSH, HMDB | | Pyruvic acid | HMDB | | alpha-Ketopropanoic acid | HMDB | | α-Ketopropanoic acid | HMDB |
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| Chemical Formula | C3H4O3 |
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| Average Molecular Weight | 88.0621 |
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| Monoisotopic Molecular Weight | 88.016043994 |
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| IUPAC Name | 2-oxopropanoic acid |
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| Traditional Name | pyruvic acid |
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| CAS Registry Number | 127-17-3 |
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| SMILES | CC(=O)C(O)=O |
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| InChI Identifier | InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6) |
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| InChI Key | LCTONWCANYUPML-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. |
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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 | Alpha-keto acids and derivatives |
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| Direct Parent | Alpha-keto acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Alpha-keto acid
- Alpha-hydroxy ketone
- Ketone
- Monocarboxylic acid or derivatives
- 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
- Mitochondria
- Peroxisome
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 13.8 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 1000.0 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Mitochondria
- Peroxisome
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| Biospecimen Locations | - Adipose Tissue
- Blood
- Brain
- Fibroblasts
- Heart
- Kidney
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Neuron
- Pancreas
- Placenta
- Ruminal Fluid
- Semimembranosus Muscle
- Spleen
- Testis
- Thyroid Gland
- Urine
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 150 +/- 40 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Heart | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 108 +/- 20 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 123 +/- 51 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | 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 | 17 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 20 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 17 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 20 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 38.03 +/- 8.02 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2 - 188 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 57.3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 24.3 +/- 29.3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 36.52 +/- 14.70 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 31.75 +/- 8.44 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1-183 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Pancreas | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 62 +/- 33 uM | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 157 +/- 68 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 11 +/- 3 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Thyroid Gland | Expected 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 | All Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Fed pasture vs barley-based concentrate | | details |
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| External Links |
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| HMDB ID | HMDB0000243 |
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| DrugBank ID | DB00119 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB031141 |
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| KNApSAcK ID | C00001200 |
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| Chemspider ID | Not Available |
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| KEGG Compound ID | C00022 |
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| BioCyc ID | PYRUVATE |
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| BiGG ID | Not Available |
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| Wikipedia Link | Pyruvic_acid |
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| METLIN ID | Not Available |
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| PubChem Compound | 1060 |
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| PDB ID | Not Available |
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| ChEBI ID | 32816 |
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| References |
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| Synthesis Reference | Xiang, Wei; Okita, Motomu. Preparation of pyruvic acid. Jpn. Kokai Tokkyo Koho (2003), 5 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 ]
- Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
- 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 ]
- 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 ]
- Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug 23. [PubMed:23931703 ]
- 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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