Prephenate (YMDB00324)

Identification

YMDB ID

YMDB00324

Name

Prephenate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Prephenate, also known as prephenic acid, 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. Prephenate is an extremely weak basic (essentially neutral) compound (based on its pKa). Prephenate exists in all living species, ranging from bacteria to humans. Within yeast, prephenate participates in a number of enzymatic reactions. In particular, prephenate can be biosynthesized from chorismate; which is mediated by the enzyme chorismate mutase. In addition, prephenate can be converted into 4-hydroxyphenylpyruvic acid; which is catalyzed by the enzyme prephenate dehydrogenase [nadp(+)]. In yeast, prephenate is involved in the metabolic pathway called the tyrosine metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

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

CAS number

126-49-8

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)

IUPAC Name

1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid

Traditional IUPAC Name

prephenic acid

Chemical Formula

C₁₀H₁₀O₆

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]

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

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

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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 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

Organoleptic Properties

Not Available

SMPDB Pathways

Phenylalanine metabolism	PW002437
Tyrosine metabolism	PW002441

KEGG Pathways

Phenylalanine metabolism	ec00360
Phenylalanine, tyrosine and tryptophan biosynthesis	ec00400
Tyrosine metabolism	ec00350

SMPDB Reactions

Chorismate → Prephenate

Prephenate + hydron → water + Carbon dioxide + keto-phenylpyruvic acid

Prephenate + NADP → NADPH + Carbon dioxide + (4-hydroxyphenyl)pyruvic acid

KEGG Reactions

Chorismate → Prephenate

hydron + Prephenate → Carbon dioxide + water + keto-phenylpyruvic acid

NAD + Prephenate → NADH + Carbon dioxide + (4-hydroxyphenyl)pyruvic acid

NADP + Prephenate → Carbon dioxide + (4-hydroxyphenyl)pyruvic acid + NADPH

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-004u-5930000000-ab2b31a4c4dfd40ceddb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-004u-9810000000-ac9f3a0c71b3c5665bf8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014u-8910000000-3415a97033f86fa8c8a8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004u-5930000000-ab2b31a4c4dfd40ceddb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004u-9810000000-ac9f3a0c71b3c5665bf8	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9610000000-b3ced3fa2b10936d8535	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-004l-8009100000-38ca188548d74699664b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0960000000-977e79544dc4467ac727	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bu9-1910000000-ad1d0e019512e236b48e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-3900000000-328dfece2609b4273be8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1790000000-740f63025e2d1901bfcc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06v0-1920000000-23a6bf28fe9915f6fca3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-8900000000-a949dc8f9457a7974670	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

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

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	16666
HMDB ID	HMDB12283
Pubchem Compound ID	1028
Kegg ID	C00254
ChemSpider ID	1001
FOODB ID	FDB028914
Wikipedia	Prephenic_acid
BioCyc ID	PREPHENATE

Enzymes

Protein Details

1. Cholinephosphotransferase 1

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the cholinephosphotransferase might participate in the transport process
Gene Name:: CPT1
Uniprot ID:: P17898
Molecular weight:: 44829.0

Reactions

CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.

Protein Details

2. Prephenate dehydrogenase [NADP+]

General function:: Involved in oxidoreductase activity
Specific function:: Prephenate + NADP(+) = 4-hydroxyphenylpyruvate + CO(2) + NADPH
Gene Name:: TYR1
Uniprot ID:: P20049
Molecular weight:: 50922.89844

Reactions

Prephenate + NADP(+) → 4-hydroxyphenylpyruvate + CO(2) + NADPH.

Protein Details

3. Chorismate mutase

General function:: Involved in chorismate mutase activity
Specific function:: Chorismate = prephenate
Gene Name:: ARO7
Uniprot ID:: P32178
Molecular weight:: 29746.80078

Reactions

Chorismate → prephenate.

Protein Details

4. Putative prephenate dehydratase

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).

Structure for #<Compound:0xadde11e4>

Enzymes

Reactions

Reactions

Reactions

Reactions