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Record Information
Version	2.0
Creation Date	2012-05-31 14:21:37 -0600
Update Date	2015-06-03 17:19:04 -0600
Secondary Accession Numbers	ECMDB12283
Identification
Name:	Prephenate
Description	Prephenic acid, more commonly known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaa984360> Close
Synonyms:	1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvate 1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acid PRE Prephenic acid
Chemical Formula:	C10H10O6
Weight:	Average: 226.1828 Monoisotopic: 226.047738052
InChI Key:	FPWMCUPFBRFMLH-UHFFFAOYSA-N
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)
CAS number:	126-49-8
IUPAC Name:	1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
Traditional IUPAC Name:	prephenic acid
SMILES:	OC1C=CC(CC(=O)C(O)=O)(C=C1)C(O)=O
Chemical Taxonomy
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub Class	Gamma-keto acids and derivatives
Direct Parent	Gamma-keto acids and derivatives
Alternative Parents	Dicarboxylic acids and derivatives Alpha-keto acids and derivatives Alpha-hydroxy ketones Secondary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives
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
Molecular Framework	Aliphatic homomonocyclic compounds
External Descriptors	oxo dicarboxylic acid (CHEBI:16666 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 36 g/L ALOGPS logP -0.31 ALOGPS logP 0.061 ChemAxon logS -0.8 ALOGPS pKa (Strongest Acidic) 2.89 ChemAxon pKa (Strongest Basic) -2.1 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 111.9 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 53.55 m³·mol⁻¹ ChemAxon Polarizability 19.73 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Chorismate <> Prephenate Hydrogen ion + Prephenate > Carbon dioxide + Water + Phenylpyruvic acid NAD + Prephenate > 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADH Prephenate <> Phenylpyruvic acid + Water + Carbon dioxide Prephenate + NAD <> 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADH + Hydrogen ion Oxalacetic acid + L-Arogenate <> L-Aspartic acid + Prephenate Chorismate > Prephenate Prephenate > Phenylpyruvic acid + Water + Carbon dioxide Prephenate + NAD > 4-hydroxyphenylpyruvate + Carbon dioxide + NADH Chorismate <> Prephenate Hydrogen ion + Prephenate > Carbon dioxide + Water + Phenylpyruvic acid Chorismate <> Prephenate
SMPDB Pathways:	Phenylalanine metabolism PW000921 phenylalanine biosynthesis PW000807 tyrosine biosynthesis PW000806
KEGG Pathways:	Metabolic pathways eco01100 Novobiocin biosynthesis ec00401 Phenylalanine metabolism ec00360 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
EcoCyc Pathways:	phenylalanine biosynthesis I PHESYN tyrosine biosynthesis I TYRSYN
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS) splash10-004u-5930000000-ab2b31a4c4dfd40ceddb View in MoNA GC-MS GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS) splash10-004u-9810000000-ac9f3a0c71b3c5665bf8 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014u-8910000000-3415a97033f86fa8c8a8 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-004u-5930000000-ab2b31a4c4dfd40ceddb View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-004u-9810000000-ac9f3a0c71b3c5665bf8 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0006-9610000000-b3ced3fa2b10936d8535 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-004l-8009100000-38ca188548d74699664b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4i-0960000000-977e79544dc4467ac727 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0bu9-1910000000-ad1d0e019512e236b48e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-3900000000-328dfece2609b4273be8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-1790000000-740f63025e2d1901bfcc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-06v0-1920000000-23a6bf28fe9915f6fca3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-000f-8900000000-a949dc8f9457a7974670 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 29934 HMDB ID HMDB12283 Pubchem Compound ID 1028 Kegg ID C00254 ChemSpider ID 1001 Wikipedia ID Prephenic_acid BioCyc ID PREPHENATE EcoCyc ID PREPHENATE

Enzymes