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Identification
YMDB IDYMDB00324
NamePrephenate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPrephenate, 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 through the action of the enzyme prephenate dehydrogenase [nadp(+)]. In yeast, prephenate is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
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 number126-49-8
WeightAverage: 226.1828
Monoisotopic: 226.047738052
InChI KeyFPWMCUPFBRFMLH-UHFFFAOYSA-N
InChIInChI=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 Name1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
Traditional IUPAC Nameprephenic acid
Chemical FormulaC10H10O6
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.
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Organoleptic PropertiesNot Available
SMPDB Pathways
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
Tyrosine metabolismPW002441 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Phenylalanine metabolismec00360 Map00360
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
Tyrosine metabolismec00350 Map00350
SMPDB Reactions
ChorismatePrephenate
Prephenate + hydronwater + Carbon dioxide + keto-phenylpyruvic acid
Prephenate + NADPNADPH + Carbon dioxide + (4-hydroxyphenyl)pyruvic acid
KEGG Reactions
ChorismatePrephenate
hydron + PrephenateCarbon dioxide + water + keto-phenylpyruvic acid
NAD + PrephenateNADH + Carbon dioxide + (4-hydroxyphenyl)pyruvic acid
NADP + PrephenateCarbon dioxide + (4-hydroxyphenyl)pyruvic acid + NADPH
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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:
ResourceLink
CHEBI ID16666
HMDB IDHMDB12283
Pubchem Compound ID1028
Kegg IDC00254
ChemSpider ID1001
FOODB IDFDB028914
WikipediaPrephenic_acid
BioCyc IDPREPHENATE

Enzymes

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