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Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:48:59 UTC |
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HMDB ID | HMDB0000205 |
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Secondary Accession Numbers | - HMDB0001237
- HMDB00205
- HMDB0031629
- HMDB01237
- HMDB31629
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Metabolite Identification |
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Common Name | Phenylpyruvic acid |
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Description | Phenylpyruvic acid is a keto-acid that is an intermediate or catabolic byproduct of phenylalanine metabolism. It has a slight honey-like odor. Levels of phenylpyruvate are normally very low in blood or urine. High levels of phenylpyruvic acid can be found in the urine of individuals with phenylketonuria (PKU), an inborn error of metabolism. PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid. In particular, excessive phenylalanine can be metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. Phenylpyruvic acid is also a microbial metabolite, it can be produced by Lactobacillus plantarum (PMID: 9687465 ). |
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Structure | 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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Synonyms | Value | Source |
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3-Phenyl-2-oxopropanoate | ChEBI | 3-Phenyl-2-oxopropanoic acid | ChEBI | 3-Phenylpyruvic acid | ChEBI | alpha-Ketohydrocinnamic acid | ChEBI | alpha-Oxo-benzenepropanoic acid | ChEBI | beta-Phenylpyruvic acid | ChEBI | Keto-phenylpyruvate | ChEBI | Phenylbrenztraubensaeure | ChEBI | Phenylpyruvate | ChEBI | 3-PHENYLPYRUVate | Generator | a-Ketohydrocinnamate | Generator | a-Ketohydrocinnamic acid | Generator | alpha-Ketohydrocinnamate | Generator | α-Ketohydrocinnamate | Generator | α-Ketohydrocinnamic acid | Generator | a-Oxo-benzenepropanoate | Generator | a-Oxo-benzenepropanoic acid | Generator | alpha-Oxo-benzenepropanoate | Generator | α-Oxo-benzenepropanoate | Generator | α-Oxo-benzenepropanoic acid | Generator | b-Phenylpyruvate | Generator | b-Phenylpyruvic acid | Generator | beta-Phenylpyruvate | Generator | β-Phenylpyruvate | Generator | β-Phenylpyruvic acid | Generator | keto-Phenylpyruvic acid | Generator | 2-Oxo-3-phenylpropanoate | HMDB, KEGG | 2-Oxo-3-phenylpropanoic acid | HMDB, Generator | a-Hydroxycinnamic acid | HMDB | FEMA 3892 | HMDB | Phenylpyruvic acid | ChEBI | 2-Oxo-3-phenylpropionic acid | HMDB | 3-Phenyl-2-oxopropionic acid | HMDB | alpha-Oxobenzenepropanoic acid | HMDB | alpha-Oxobenzenepropionic acid | HMDB | α-Oxobenzenepropanoic acid | HMDB | α-Oxobenzenepropionic acid | HMDB |
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Chemical Formula | C9H8O3 |
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Average Molecular Weight | 164.158 |
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Monoisotopic Molecular Weight | 164.047344122 |
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IUPAC Name | 2-oxo-3-phenylpropanoic acid |
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Traditional Name | phenylpyruvic acid |
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CAS Registry Number | 156-06-9 |
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SMILES | OC(=O)C(=O)CC1=CC=CC=C1 |
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InChI Identifier | 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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InChI Key | BTNMPGBKDVTSJY-UHFFFAOYSA-N |
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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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Ontology |
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Physiological effect
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Adverse health effect
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Disposition
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Biological location
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Process
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Naturally occurring process
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 154 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 112 mg/mL | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Phenylpyruvic acid,1TMS,isomer #1 | C[Si](C)(C)OC(=O)C(=O)CC1=CC=CC=C1 | 1517.2 | Semi standard non polar | 33892256 | Phenylpyruvic acid,1TMS,isomer #2 | C[Si](C)(C)OC(=CC1=CC=CC=C1)C(=O)O | 1669.7 | Semi standard non polar | 33892256 | Phenylpyruvic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C | 1615.5 | Semi standard non polar | 33892256 | Phenylpyruvic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C | 1695.2 | Standard non polar | 33892256 | Phenylpyruvic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C | 1898.4 | Standard polar | 33892256 | Phenylpyruvic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CC=CC=C1 | 1747.9 | Semi standard non polar | 33892256 | Phenylpyruvic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=CC1=CC=CC=C1)C(=O)O | 1924.3 | Semi standard non polar | 33892256 | Phenylpyruvic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C | 2099.9 | Semi standard non polar | 33892256 | Phenylpyruvic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C | 2101.6 | Standard non polar | 33892256 | Phenylpyruvic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C | 2186.3 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-00ko-9700000000-1a891469df1de787159b | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0006-1900000000-7dc1a5344d13e4dc19ac | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-001i-0900000000-bbbc84c54d03c4a14e51 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0a4i-0900000000-00b547b0371603520b61 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS; 1 MEOX) | splash10-00di-9100000000-fdd48b632e63c8478078 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-MS (1 MEOX; 1 TMS) | splash10-000f-9300000000-8cd32f87e04ae0b6d6fb | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-MS (1 MEOX; 1 TMS) | splash10-014u-9720000000-7a0b66e6c18ff42ac05e | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-MS (2 TMS) | splash10-0006-9760000000-d94111a7b9babceb265b | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Non-derivatized) | splash10-00ko-9700000000-1a891469df1de787159b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Non-derivatized) | splash10-00di-9100000000-fdd48b632e63c8478078 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized) | splash10-000f-9300000000-8cd32f87e04ae0b6d6fb | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized) | splash10-014u-9720000000-7a0b66e6c18ff42ac05e | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized) | splash10-0006-9760000000-d94111a7b9babceb265b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized) | splash10-000f-9300000000-8cd32f87e04ae0b6d6fb | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized) | splash10-014u-9720000000-7a0b66e6c18ff42ac05e | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized) | splash10-0006-9760000000-d94111a7b9babceb265b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Non-derivatized) | splash10-00ko-9700000000-cec4a53271b8d66c2abc | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9300000000-9a8a36c751256480752e | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (1 TMS) - 70eV, Positive | splash10-00r6-9500000000-3e83cb905f1fd4362497 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-00kf-9300000000-d1a7d23e7c5270b16883 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Phenylpyruvic acid Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-066r-0900000000-ceb2ce23352e0f45ee33 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Phenylpyruvic acid Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-004i-9200000000-ed4a6740d574858da982 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Phenylpyruvic acid Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-004i-9000000000-c239a9a599daa607e47f | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Phenylpyruvic acid LC-ESI-QFT , negative-QTOF | splash10-014i-0900000000-36e00f6baa5d907e851b | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Phenylpyruvic acid LC-ESI-QTOF 35V, negative-QTOF | splash10-014i-0900000000-843a66173124c8fdf184 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Phenylpyruvic acid 35V, Negative-QTOF | splash10-014i-0900000000-272f6079d347e1b34e86 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 10V, Positive-QTOF | splash10-014j-1900000000-5d025096b1bb0e80dc1c | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 20V, Positive-QTOF | splash10-014m-3900000000-9d0be907ecb6cc5efe8c | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 40V, Positive-QTOF | splash10-0006-9200000000-a4fc563b3536eafc044d | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 10V, Negative-QTOF | splash10-03di-1900000000-0f660ae6dc074d939404 | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 20V, Negative-QTOF | splash10-014j-1900000000-d229883bf098b04e0fcb | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 40V, Negative-QTOF | splash10-014i-5900000000-a107b725b71a6441a80c | 2016-09-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 10V, Negative-QTOF | splash10-03xr-1900000000-8ba05dd4c5612aae9f50 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 20V, Negative-QTOF | splash10-0006-9300000000-946fa61c2a2596d7592d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 40V, Negative-QTOF | splash10-0006-9200000000-fa13a9bfbb6c03b2e12d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 10V, Positive-QTOF | splash10-014l-4900000000-2d56731d3ebcebf8079a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 20V, Positive-QTOF | splash10-0006-9200000000-9b3ae8fbf3992b1b2f28 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 40V, Positive-QTOF | splash10-0006-9000000000-089373761153dce3ca74 | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.5 +/- 0.1 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 5 uM | Children (1 - 13 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.17 (0.05-0.67) umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 0.24 (0.10-0.76) umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.00064 +/- 0.000544 umol/mmol creatinine | Newborn (0-30 days old) | Not Specified | Normal | | details | Urine | Detected and Quantified | <2 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.138 +/- 0.207 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 0.207 +/- 0.275 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 0.207 +/- 0.344 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 0.25 +/- 0.43 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 50.0 (40.0-60.0) uM | Newborn (0-30 days old) | Both | Phenylketonuria | | details | Blood | Detected and Quantified | 1.4 +/- 0.2 uM | Adult (>18 years old) | Both | Primary biliary cirrhosis | | details | Urine | Detected and Quantified | 7796.386 umol/mmol creatinine | Infant (0-1 year old) | Male | Phenylketonuria | | details | Urine | Detected and Quantified | 31047.8 umol/mmol creatinine | Children (1 - 13 years old) | Male | Phenylketonuria | | details | Urine | Detected and Quantified | 255.518 +/- 250.00780 umol/mmol creatinine | Children (1-13 years old) | Both | Phenylketonuria | | details | Urine | Detected and Quantified | 735.560 +/- 528.253 umol/mmol creatinine | Children (1-13 years old) | Both | Phenylketonuria | | details | Urine | Detected and Quantified | 882.948 +/- 741.0699 umol/mmol creatinine | Children (1-13 years old) | Both | Phenylketonuria | | details | Urine | Detected and Quantified | 146.6 +/- 244.6 umol/mmol creatinine | Newborn (0-30 days old) | Both | Phenylketonuria | | details |
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Associated Disorders and Diseases |
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Disease References | Phenylketonuria |
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- Langenbeck U, Behbehani A, Luthe H: Renal transport of aromatic acids in patients with phenylketonuria. J Inherit Metab Dis. 1981;4(2):69-70. [PubMed:6790852 ]
- Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
- Swarna M, Jyothy A, Usha Rani P, Reddy PP: Amino acid disorders in mental retardation: a two-decade study from Andhra Pradesh. Biochem Genet. 2004 Apr;42(3-4):85-98. [PubMed:15168722 ]
- Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
- G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
| Primary biliary cirrhosis |
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- Turchany JM, Leung PS, Iwayama T, Jefferson DM, Ishida J, Yamaguchi M, Munoz S, Danner DJ, Dickson ER, Gershwin ME: Comparative metabolism and structure of BCKD-E2 in primary biliary cirrhosis. J Autoimmun. 1993 Aug;6(4):459-66. [PubMed:8216688 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB03884 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB008272 |
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KNApSAcK ID | C00000751 |
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Chemspider ID | 972 |
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KEGG Compound ID | C00166 |
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BioCyc ID | PHENYL-PYRUVATE |
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BiGG ID | 34111 |
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Wikipedia Link | Phenylpyruvic_acid |
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METLIN ID | 328 |
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PubChem Compound | 997 |
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PDB ID | Not Available |
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ChEBI ID | 30851 |
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Food Biomarker Ontology | Not Available |
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VMH ID | PHPYR |
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MarkerDB ID | MDB00000098 |
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Good Scents ID | Not Available |
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References |
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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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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
- Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
- Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
- Lasala JM, Coscia CJ: Accumulation of a tetrahydroisoquinoline in phenylketonuria. Science. 1979 Jan 19;203(4377):283-4. [PubMed:153583 ]
- Cassidei L, Dell'atti A, Sciacovelli O: Improvement of the FeCl3 test for phenylpyruvic acid. Clin Chim Acta. 1978 Dec 1;90(2):121-7. [PubMed:719897 ]
- Michals K, Matalon R: Phenylalanine metabolites, attention span and hyperactivity. Am J Clin Nutr. 1985 Aug;42(2):361-5. [PubMed:4025205 ]
- Nakahara T, Ishida J, Yamaguchi M, Nakamura M: Determination of alpha-keto acids including phenylpyruvic acid in human plasma by high-performance liquid chromatography with chemiluminescence detection. Anal Biochem. 1990 Nov 1;190(2):309-13. [PubMed:2291475 ]
- Nierop Groot MN, de Bont JAM: Conversion of phenylalanine to benzaldehyde initiated by an aminotransferase in lactobacillus plantarum Appl Environ Microbiol. 1998 Aug;64(8):3009-13. [PubMed:9687465 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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