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Identification |
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YMDB ID | YMDB00786 |
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Name | keto-phenylpyruvic acid |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Phenylpyruvic acid, also known as keto-phenylpyruvate or a-ketohydrocinnamate, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. Phenylpyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylpyruvic acid exists in all living species, ranging from bacteria to humans. In yeast, phenylpyruvic acid is involved in the metabolic pathway called the phenylalanine metabolism pathway. Phenylpyruvic acid is a potentially toxic compound. |
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Structure | |
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Synonyms | - 2-Hydroxy-3-phenylpropenoic acid
- 2-Oxo-3-phenylpropanoate
- 2-Oxo-3-phenylpropanoic acid
- 3-(4-hydroxyphenyl)pyruvate
- 3-phenyl-2-oxopropanoate
- 3-Phenyl-2-oxopropanoic acid
- 3-Phenylpyruvate
- 3-Phenylpyruvic acid
- alpha-Ketohydrocinnamate
- alpha-ketohydrocinnamic acid
- alpha-oxo-benzenepropanoic acid
- b-Phenylpyruvate
- b-Phenylpyruvic acid
- Benzenepropanoic acid, .alpha.-oxo-
- beta-Phenylpyruvate
- beta-Phenylpyruvic acid
- keto-phenylpyruvate
- Phenylbrenztraubensaeure
- Phenylpyroracemate
- Phenylpyroracemic acid
- Phenylpyruvate
- phenylpyruvic acid
- Pyruvic acid, phenyl-
- a-Ketohydrocinnamate
- a-Ketohydrocinnamic acid
- α-Ketohydrocinnamate
- α-Ketohydrocinnamic acid
- a-Oxo-benzenepropanoate
- a-Oxo-benzenepropanoic acid
- alpha-Oxo-benzenepropanoate
- α-Oxo-benzenepropanoate
- α-Oxo-benzenepropanoic acid
- β-Phenylpyruvate
- β-Phenylpyruvic acid
- keto-Phenylpyruvic acid
- a-Hydroxycinnamic acid
- FEMA 3892
- 2-Oxo-3-phenylpropionic acid
- 3-Phenyl-2-oxopropionic acid
- alpha-Oxobenzenepropanoic acid
- alpha-Oxobenzenepropionic acid
- α-Oxobenzenepropanoic acid
- α-Oxobenzenepropionic acid
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CAS number | 156-06-9 |
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Weight | Average: 164.158 Monoisotopic: 164.047344122 |
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InChI Key | BTNMPGBKDVTSJY-UHFFFAOYSA-N |
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InChI | InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12) |
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IUPAC Name | 2-oxo-3-phenylpropanoic acid |
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Traditional IUPAC Name | phenylpyruvic acid |
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Chemical Formula | C9H8O3 |
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SMILES | OC(=O)C(=O)CC1=CC=CC=C1 |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Phenylpyruvic acid derivatives |
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Direct Parent | Phenylpyruvic acid derivatives |
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Alternative Parents | |
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Substituents | - Phenylpyruvate
- 3-phenylpropanoic-acid
- Keto acid
- 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
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | 154 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways | Phenylalanine metabolism | ec00360 |  | Phenylalanine, tyrosine and tryptophan biosynthesis | ec00400 |  | Tryptophan metabolism | ec00380 |  |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-00ko-9700000000-1a891469df1de787159b | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0006-1900000000-7dc1a5344d13e4dc19ac | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-001i-0900000000-bbbc84c54d03c4a14e51 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0a4i-0900000000-00b547b0371603520b61 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS; 1 MEOX) | splash10-00di-9100000000-fdd48b632e63c8478078 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-000f-9300000000-8cd32f87e04ae0b6d6fb | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS) | splash10-014u-9720000000-7a0b66e6c18ff42ac05e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0006-9760000000-d94111a7b9babceb265b | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00ko-9700000000-1a891469df1de787159b | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9100000000-fdd48b632e63c8478078 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-000f-9300000000-8cd32f87e04ae0b6d6fb | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014u-9720000000-7a0b66e6c18ff42ac05e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0006-9760000000-d94111a7b9babceb265b | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-000f-9300000000-8cd32f87e04ae0b6d6fb | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014u-9720000000-7a0b66e6c18ff42ac05e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0006-9760000000-d94111a7b9babceb265b | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00ko-9700000000-cec4a53271b8d66c2abc | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9300000000-9a8a36c751256480752e | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00r6-9500000000-3e83cb905f1fd4362497 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-066r-0900000000-ceb2ce23352e0f45ee33 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-9200000000-ed4a6740d574858da982 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-004i-9000000000-c239a9a599daa607e47f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-014i-0900000000-36e00f6baa5d907e851b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative | splash10-014i-0900000000-843a66173124c8fdf184 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-014i-0900000000-272f6079d347e1b34e86 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-1900000000-5d025096b1bb0e80dc1c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014m-3900000000-9d0be907ecb6cc5efe8c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9200000000-a4fc563b3536eafc044d | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-1900000000-0f660ae6dc074d939404 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014j-1900000000-d229883bf098b04e0fcb | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-5900000000-a107b725b71a6441a80c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03xr-1900000000-8ba05dd4c5612aae9f50 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9300000000-946fa61c2a2596d7592d | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9200000000-fa13a9bfbb6c03b2e12d | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014l-4900000000-2d56731d3ebcebf8079a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9200000000-9b3ae8fbf3992b1b2f28 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-089373761153dce3ca74 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-00kf-9300000000-d1a7d23e7c5270b16883 | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Vuralhan, Z., Morais, M. A., Tai, S. L., Piper, M. D., Pronk, J. T. (2003). "Identification and characterization of phenylpyruvate decarboxylase genes in Saccharomyces cerevisiae." Appl Environ Microbiol 69:4534-4541.12902239
- Iraqui, I., Vissers, S., Cartiaux, M., Urrestarazu, A. (1998). "Characterisation of Saccharomyces cerevisiae ARO8 and ARO9 genes encoding aromatic aminotransferases I and II reveals a new aminotransferase subfamily." Mol Gen Genet 257:238-248.9491083
- Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
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Synthesis Reference: | Li, Hongbin; Luo, Yuzhong. Preparation of phenyl-pyruvic acid by dicarbonylation of benzyl halide. Faming Zhuanli Shenqing Gongkai Shuomingshu (1996), 5 pp. |
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External Links: | |
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