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| Identification |
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| YMDB ID | YMDB00324 |
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| Name | Prephenate |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | Prephenatephenate, also known as prephenatephenate, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Prephenatephenate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Prephenatephenate exists in all living species, ranging from bacteria to humans. Prephenatephenate participates in a number of enzymatic reactions, within yeast. In particular, Prephenatephenate can be biosynthesized from chorismate; which is catalyzed by the enzyme chorismate mutase. Furthermore, Prephenatephenate can be converted into 4-hydroxyphenylpyruvic acid through its interaction with the enzyme prephenatephenate dehydrogenase [nadp(+)]. Furthermore, Prephenatephenate can be biosynthesized from chorismate; which is mediated by the enzyme chorismate mutase. Finally, Prephenatephenate can be converted into 2-oxo-3-phenylpropanoic acid (mixture oxo and keto) through the action of the enzyme prephenatephenate dehydratase. In yeast, prephenatephenate is involved in a couple of metabolic pathways, which include the tyrosine metabolism pathway and the phenylalanine metabolism pathway. |
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| Structure | |
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| Synonyms | - 1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acid
- PRE
- Prephenate
- Prephenic acid
- 1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid
- 1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvate
- 1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoate
- 1-Carboxy-4-hydroxy-a-oxo-2,5-cyclohexadiene-1-propanoic acid
- 1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoate
- 1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoate
- 1-Carboxy-4-hydroxy-α-oxo-2,5-cyclohexadiene-1-propanoic acid
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| CAS number | 126-49-8 |
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| Weight | Average: 226.1828
Monoisotopic: 226.047738052 |
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| InChI Key | FPWMCUPFBRFMLH-UHFFFAOYSA-N |
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| InChI | InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16) |
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| IUPAC Name | 1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid |
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| Traditional IUPAC Name | prephenic acid |
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| Chemical Formula | C10H10O6 |
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| SMILES | [H]OC(=O)C(=O)C([H])([H])C1(C([H])=C([H])C([H])(O[H])C([H])=C1[H])C(=O)O[H] |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. |
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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 | Gamma-keto acids and derivatives |
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| Direct Parent | Gamma-keto acids and derivatives |
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| Alternative Parents | |
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| Substituents | - Gamma-keto acid
- Dicarboxylic acid or derivatives
- Alpha-keto acid
- Alpha-hydroxy ketone
- Secondary alcohol
- Ketone
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homomonocyclic compound
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| Molecular Framework | Aliphatic 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 | Not Available |
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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 |  | | Tyrosine metabolism | ec00350 |  |
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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 |
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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
- Mannhaupt, G., Stucka, R., Pilz, U., Schwarzlose, C., Feldmann, H. (1989). "Characterization of the prephenate dehydrogenase-encoding gene, TYR1, from Saccharomyces cerevisiae." Gene 85:303-311.2697638
- Ball, S. G., Wickner, R. B., Cottarel, G., Schaus, M., Tirtiaux, C. (1986). "Molecular cloning and characterization of ARO7-OSM2, a single yeast gene necessary for chorismate mutase activity and growth in hypertonic medium." Mol Gen Genet 205:326-330.3027508
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| Synthesis Reference: | Not Available |
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| External Links: | |
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