Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:08:00 UTC |
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Update date | 2020-09-17 15:40:41 UTC |
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Primary ID | FDB008272 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto) |
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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. Within humans, phenylpyruvic acid participates in a number of enzymatic reactions. In particular, phenylpyruvic acid and L-glutamic acid can be biosynthesized from L-phenylalanine and oxoglutaric acid; which is mediated by the enzyme aspartate aminotransferase, cytoplasmic. In addition, phenylpyruvic acid can be biosynthesized from L-phenylalanine through the action of the enzyme L-amino-acid oxidase. In humans, phenylpyruvic acid is involved in the metabolic disorder called tyrosinemia type 3 (tyro3). Phenylpyruvic acid is a potentially toxic compound. Phenylpyruvic acid, with regard to humans, has been found to be associated with the diseases such as primary biliary cirrhosis; phenylpyruvic acid has also been linked to the inborn metabolic disorder phenylketonuria. High levels of phenylpyruvic acid can be found in the urine of individuals with phenylketonuria (PKU), an inborn error of metabolism. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid. Metabolites of this transamination reaction include phenylacetate, Phenylpyruvic acid and phenethylamine. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. 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. |
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CAS Number | 156-06-9 |
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Structure | |
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Synonyms | Synonym | 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 | 2-Hydroxy-3-phenyl-2-propenoic acid, 9CI | db_source | 2-oxo-3-Phenylpropanoate | HMDB | 3-PHENYLPYRUVIC ACID | ChEBI | a-oxo-Benzenepropanoate | Generator | a-oxo-Benzenepropanoic acid | Generator | a-Oxobenzenepropanoic acid, 9CI | db_source | alpha-oxo-Benzenepropanoate | Generator | alpha-oxo-Benzenepropanoic acid | ChEBI | keto-Phenylpyruvate | ChEBI | Phenylpyroracemate | HMDB | Phenylpyroracemic acid | HMDB | α-ketohydrocinnamate | Generator | α-ketohydrocinnamic acid | Generator | α-oxo-benzenepropanoate | Generator | α-oxo-benzenepropanoic acid | Generator | β-phenylpyruvate | Generator | β-phenylpyruvic acid | Generator |
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Predicted Properties | |
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Chemical Formula | C9H8O3 |
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IUPAC name | 2-oxo-3-phenylpropanoic acid |
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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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Isomeric SMILES | OC(=O)C(=O)CC1=CC=CC=C1 |
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Average Molecular Weight | 164.158 |
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Monoisotopic Molecular Weight | 164.047344122 |
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Classification |
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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 | Health effect: |
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Disposition | Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 65.85%; H 4.91%; O 29.24% | DFC |
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Melting Point | Mp 157° dec. | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-00kf-9300000000-d1a7d23e7c5270b16883 | 2014-09-20 | View Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 TMS, GC-MS Spectrum | splash10-00ko-9700000000-1a891469df1de787159b | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-0006-1900000000-7dc1a5344d13e4dc19ac | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-001i-0900000000-bbbc84c54d03c4a14e51 | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-0a4i-0900000000-00b547b0371603520b61 | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 TMS; 1 MEOX, GC-MS Spectrum | splash10-00di-9100000000-fdd48b632e63c8478078 | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 MEOX; 1 TMS, GC-MS Spectrum | splash10-000f-9300000000-8cd32f87e04ae0b6d6fb | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 MEOX; 1 TMS, GC-MS Spectrum | splash10-014u-9720000000-7a0b66e6c18ff42ac05e | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 2 TMS, GC-MS Spectrum | splash10-0006-9760000000-d94111a7b9babceb265b | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-00ko-9700000000-1a891469df1de787159b | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-00di-9100000000-fdd48b632e63c8478078 | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-000f-9300000000-8cd32f87e04ae0b6d6fb | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-014u-9720000000-7a0b66e6c18ff42ac05e | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-0006-9760000000-d94111a7b9babceb265b | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-000f-9300000000-8cd32f87e04ae0b6d6fb | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-014u-9720000000-7a0b66e6c18ff42ac05e | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-0006-9760000000-d94111a7b9babceb265b | Spectrum | GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, GC-MS Spectrum | splash10-00ko-9700000000-cec4a53271b8d66c2abc | Spectrum | Predicted GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9300000000-9a8a36c751256480752e | Spectrum | Predicted GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00r6-9500000000-3e83cb905f1fd4362497 | Spectrum | Predicted GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto), TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-066r-0900000000-ceb2ce23352e0f45ee33 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-9200000000-ed4a6740d574858da982 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-004i-9000000000-c239a9a599daa607e47f | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-014i-0900000000-36e00f6baa5d907e851b | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative | splash10-014i-0900000000-843a66173124c8fdf184 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-014i-0900000000-272f6079d347e1b34e86 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-1900000000-5d025096b1bb0e80dc1c | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014m-3900000000-9d0be907ecb6cc5efe8c | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9200000000-a4fc563b3536eafc044d | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-1900000000-0f660ae6dc074d939404 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014j-1900000000-d229883bf098b04e0fcb | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-5900000000-a107b725b71a6441a80c | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03xr-1900000000-8ba05dd4c5612aae9f50 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9300000000-946fa61c2a2596d7592d | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9200000000-fa13a9bfbb6c03b2e12d | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014l-4900000000-2d56731d3ebcebf8079a | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9200000000-9b3ae8fbf3992b1b2f28 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-089373761153dce3ca74 | 2021-09-23 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 972 |
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ChEMBL ID | CHEMBL1162488 |
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KEGG Compound ID | C00166 |
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Pubchem Compound ID | 997 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB03884 |
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HMDB ID | HMDB00205 |
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CRC / DFC (Dictionary of Food Compounds) ID | DFK71-H:DFK71-H |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 34111 |
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KNApSAcK ID | C00000751 |
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HET ID | PPY |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Tyrosine aminotransferase | TAT | P17735 | Aspartate aminotransferase, cytoplasmic | GOT1 | P17174 | Aspartate aminotransferase, mitochondrial | GOT2 | P00505 | Kynurenine--oxoglutarate transaminase 1 | CCBL1 | Q16773 | Macrophage migration inhibitory factor | MIF | P14174 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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