P. aeruginosa Metabolome Database: Prephenate (PAMDB000839)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000839

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

🔍MOL SDF PDB SMILES InChI View Structure

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

Average Molecular Weight:

226.1828

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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

Substituents

Gamma-keto acid
Dicarboxylic acid or derivatives
Alpha-keto acid
Cyclic alcohol
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
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	36.0 mg/mL	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 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.55 m³·mol^-1	ChemAxon
Polarizability	19.73 Å³	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
Prephenate <> Phenylpyruvic acid + Water + Carbon dioxide
Prephenate + NAD <> 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADH + Hydrogen ion
Hydrogen ion + Prephenate > Phenylpyruvic acid + Water + Carbon dioxide
Prephenate + NAD > 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADH
Prephenate + NAD > NADH + Carbon dioxide + 4-hydroxyphenylpyruvate

Pathways:

Metabolic pathways pae01100
Novobiocin biosynthesis pae00401
Phenylalanine metabolism pae00360
Phenylalanine, tyrosine and tryptophan biosynthesis pae00400

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-MS	Not Available
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

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

Prephenate (PAMDB000839)

Structure for Prephenate (PAMDB000839)