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keto-phenylpyruvic acid (YMDB00786)
| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| YMDB ID | YMDB00786 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name | keto-phenylpyruvic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Species | Saccharomyces cerevisiae | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Strain | Baker's yeast | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms |
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| CAS number | 156-06-9 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight | Average: 164.158 Monoisotopic: 164.047344122 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key | BTNMPGBKDVTSJY-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI | InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name | 2-oxo-3-phenylpropanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name | phenylpyruvic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Formula | C9H8O3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES | OC(=O)C(=O)CC1=CC=CC=C1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Benzenoids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Benzene and substituted derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Phenylpyruvic acid derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Phenylpyruvic acid derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aromatic homomonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point | 154 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations |
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| Organoleptic Properties | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways |
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| KEGG Pathways |
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| SMPDB Reactions | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Reactions | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Intracellular Concentrations | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Extracellular Concentrations | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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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Enzymes
- General function:
- Involved in magnesium ion binding
- Specific function:
- Second most abundant of three pyruvate decarboxylases (PDC1, PDC5, PDC6) implicated in the nonoxidative conversion of pyruvate to acetaldehyde and carbon dioxide during alcoholic fermentation. Most of the produced acetaldehyde is subsequently reduced to ethanol, but some is required for cytosolic acetyl-CoA production for biosynthetic pathways. The enzyme is also one of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) able to decarboxylate more complex 2-oxo acids (alpha-keto-acids) than pyruvate, which seem mainly involved in amino acid catabolism. Here the enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids. In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids valine, isoleucine, phenylalanine, and tryptophan, whereas leucine is no substrate. In a side-reaction the carbanionic intermediate (or active aldehyde) generated by decarboxylation or by activation of an aldehyde can react with an aldehyde via condensation (or carboligation) yielding a 2-hydroxy ketone, collectively called acyloins
- Gene Name:
- PDC5
- Uniprot ID:
- P16467
- Molecular weight:
- 61911.60156
Reactions
| A 2-oxo acid → an aldehyde + CO(2). |
| 3-(indol-3-yl)pyruvate → 2-(indol-3-yl)acetaldehyde + CO(2). |
| Phenylpyruvate → phenylacetaldehyde + CO(2). |
| Pyruvate → Acetaldehyde + CO(2). |
| A 2-oxo acid + an aldehyde → A 2-hydroxy ketone + CO(2). |
| An aldehyde + an aldehyde → A 2-hydroxy ketone. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- Minor of three pyruvate decarboxylases (PDC1, PDC5, PDC6) implicated in the nonoxidative conversion of pyruvate to acetaldehyde and carbon dioxide during alcoholic fermentation. Most of the produced acetaldehyde is subsequently reduced to ethanol, but some is required for cytosolic acetyl-CoA production for biosynthetic pathways. The enzyme is also one of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) able to decarboxylate more complex 2-oxo acids (alpha-keto-acids) than pyruvate, which seem mainly involved in amino acid catabolism. Here the enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids. In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids valine, isoleucine, phenylalanine, and tryptophan, whereas leucine is no substrate. In a side-reaction the carbanionic intermediate (or active aldehyde) generated by decarboxylation or by activation of an aldehyde can react with an aldehyde via condensation (or carboligation) yielding a 2-hydroxy ketone, collectively called acyloins. The expression level of this protein in the presence of fermentable carbon sources is so low that it can not compensate for the other two pyruvate decarboxylases to sustain fermentation
- Gene Name:
- PDC6
- Uniprot ID:
- P26263
- Molecular weight:
- 61579.89844
Reactions
| A 2-oxo acid → an aldehyde + CO(2). |
| 3-(indol-3-yl)pyruvate → 2-(indol-3-yl)acetaldehyde + CO(2). |
| Phenylpyruvate → phenylacetaldehyde + CO(2). |
| Pyruvate → Acetaldehyde + CO(2). |
| A 2-oxo acid + an aldehyde → A 2-hydroxy ketone + CO(2). |
| An aldehyde + an aldehyde → A 2-hydroxy ketone. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- Major of three pyruvate decarboxylases (PDC1, PDC5, PDC6) implicated in the nonoxidative conversion of pyruvate to acetaldehyde and carbon dioxide during alcoholic fermentation. Most of the produced acetaldehyde is subsequently reduced to ethanol, but some is required for cytosolic acetyl-CoA production for biosynthetic pathways. The enzyme is also one of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) able to decarboxylate more complex 2-oxo acids (alpha-ketoacids) than pyruvate, which seem mainly involved in amino acid catabolism. Here the enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids. In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids valine, isoleucine, phenylalanine, and tryptophan, whereas leucine is no substrate. In a side-reaction the carbanionic intermediate (or active aldehyde) generated by decarboxylation or by activation of an aldehyde can react with an aldehyde via condensation (or carboligation) yielding a 2-hydroxy ketone, collectively called acyloins
- Gene Name:
- PDC1
- Uniprot ID:
- P06169
- Molecular weight:
- 61494.89844
Reactions
| A 2-oxo acid → an aldehyde + CO(2). |
| 3-(indol-3-yl)pyruvate → 2-(indol-3-yl)acetaldehyde + CO(2). |
| Phenylpyruvate → phenylacetaldehyde + CO(2). |
| Pyruvate → Acetaldehyde + CO(2). |
| A 2-oxo acid + an aldehyde → A 2-hydroxy ketone + CO(2). |
| An aldehyde + an aldehyde → A 2-hydroxy ketone. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- One of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) involved in amino acid catabolism. The enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids (alpha-keto-acids). In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids, phenylalanine, tryptophan, (and probably tyrosine), but also isoleucine, whereas leucine is a low efficiency and valine and pyruvate are no substrates. In analogy to the pyruvate decarboxylases the enzyme may in a side-reaction catalyze condensation (or carboligation) reactions leading to the formation of 2-hydroxy ketone, collectively called acyloins
- Gene Name:
- ARO10
- Uniprot ID:
- Q06408
- Molecular weight:
- 71383.79688
Reactions
| A 2-oxo acid → an aldehyde + CO(2). |
| Phenylpyruvate → phenylacetaldehyde + CO(2). |
| 3-(indol-3-yl)pyruvate → 2-(indol-3-yl)acetaldehyde + CO(2). |
- General function:
- Involved in transferase activity, transferring nitrogenous groups
- Specific function:
- Has aromatic amino acid transaminase activity and kynurenine aminotransferase activity
- Gene Name:
- ARO9
- Uniprot ID:
- P38840
- Molecular weight:
- 58527.0
Reactions
| An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate. |
- General function:
- Involved in transferase activity, transferring nitrogenous groups
- Specific function:
- Has aromatic amino acid transaminase activity. Also active with methionine, alpha-aminoadipate and leucine when phenylpyruvate is the amino acceptor
- Gene Name:
- ARO8
- Uniprot ID:
- P53090
- Molecular weight:
- 56177.30078
Reactions
| An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate. |
| L-2-aminoadipate + 2-oxoglutarate → 2-oxoadipate + L-glutamate |
- General function:
- Involved in prephenate dehydratase activity
- Specific function:
- Prephenate = phenylpyruvate + H(2)O + CO(2)
- Gene Name:
- PHA2
- Uniprot ID:
- P32452
- Molecular weight:
- 38224.80078
Reactions
| Prephenate → phenylpyruvate + H(2)O + CO(2). |