Record Information
Version2.0
Creation Date2012-05-31 14:21:37 -0600
Update Date2015-06-03 17:19:04 -0600
Secondary Accession Numbers
  • ECMDB12283
Identification
Name:Prephenate
DescriptionPrephenic acid, more commonly known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine.
Structure
Thumb
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility36 g/LALOGPS
logP-0.31ALOGPS
logP0.061ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.55 m³·mol⁻¹ChemAxon
Polarizability19.73 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
phenylalanine biosynthesisPW000807 ThumbThumb?image type=greyscaleThumb?image type=simple
tyrosine biosynthesisPW000806 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-004u-5930000000-ab2b31a4c4dfd40ceddbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-004u-9810000000-ac9f3a0c71b3c5665bf8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014u-8910000000-3415a97033f86fa8c8a8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004u-5930000000-ab2b31a4c4dfd40ceddbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004u-9810000000-ac9f3a0c71b3c5665bf8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9610000000-b3ced3fa2b10936d8535View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004l-8009100000-38ca188548d74699664bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0960000000-977e79544dc4467ac727View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu9-1910000000-ad1d0e019512e236b48eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-328dfece2609b4273be8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1790000000-740f63025e2d1901bfccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06v0-1920000000-23a6bf28fe9915f6fca3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-8900000000-a949dc8f9457a7974670View in MoNA
1D NMR1H NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI ID29934
HMDB IDHMDB12283
Pubchem Compound ID1028
Kegg IDC00254
ChemSpider ID1001
Wikipedia IDPrephenic_acid
BioCyc IDPREPHENATE
EcoCyc IDPREPHENATE

Enzymes

General function:
Involved in transferase activity
Specific function:
An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate
Gene Name:
tyrB
Uniprot ID:
P04693
Molecular weight:
43537
Reactions
An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate.
General function:
Involved in oxidation-reduction process
Specific function:
Chorismate = prephenate
Gene Name:
tyrA
Uniprot ID:
P07023
Molecular weight:
42042
Reactions
Chorismate = prephenate.
Prephenate + NAD(+) = 4-hydroxyphenylpyruvate + CO(2) + NADH.
General function:
Involved in chorismate mutase activity
Specific function:
Chorismate = prephenate
Gene Name:
pheA
Uniprot ID:
P0A9J8
Molecular weight:
43111
Reactions
Chorismate = prephenate.
Prephenate = phenylpyruvate + H(2)O + CO(2).