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Identification
YMDB IDYMDB00958
Name(4-hydroxyphenyl)pyruvic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-Hydroxyphenylpyruvic acid (4-HPPA) is a keto acid. It is a product of the enzyme (R)-4-hydroxyphenyllactate dehydrogenase [EC 1.1.1.222] and is formed during tyrosine metabolism. There are two isomers of HPPA, specifically 4HPPA and 3HPPA, of which 4HPPA is the most common. The enzyme 4-hydroxyphenylpyruvic acid dioxygenase (HPD) catalyzes the reaction of 4-hydroxyphenylpyruvic acid to homogentisic acid in the tyrosine catabolism pathway. [KEGG]
Structure
Thumb
Synonyms
  • (p-hydroxyphenyl)-Pyruvate
  • (p-hydroxyphenyl)-Pyruvic acid
  • (p-Hydroxyphenyl)pyruvate
  • (p-Hydroxyphenyl)pyruvic acid
  • 3-(4-HYDROXY-PHENYL)PYRUVIC ACID
  • 3-(4-hydroxyphenyl)-2-oxo-propanoate
  • 3-(4-hydroxyphenyl)-2-oxo-propanoic acid
  • 3-(4-Hydroxyphenyl)-2-oxopropanoic acid
  • 3-(4-Hydroxyphenyl)-2-oxopropionate
  • 3-(4-Hydroxyphenyl)-2-oxopropionic acid
  • 3-(4-Hydroxyphenyl)pyruvate
  • 3-(4-Hydroxyphenyl)pyruvic acid
  • 3-(p-Hydroxyphenyl)-2-oxopropanoic acid
  • 3-(p-Hydroxyphenyl)-2-oxopropionate
  • 3-(p-Hydroxyphenyl)-2-oxopropionic acid
  • 3-(p-Hydroxyphenyl)pyruvate
  • 3-(p-Hydroxyphenyl)pyruvic acid
  • 4-hydroxy alpha-oxobenzenepropanoic acid
  • 4-Hydroxy-a-oxobenzenepropanoate
  • 4-Hydroxy-a-oxobenzenepropanoic acid
  • 4-Hydroxy-alpha-oxobenzenepropanoate
  • 4-Hydroxy-alpha-oxobenzenepropanoic acid
  • 4-hydroxyphenylpyruvate
  • 4-Hydroxyphenylpyruvic acid
  • 4HPPA
  • Benzenepropanoic acid, 4-hydroxy-.alpha.-oxo-
  • HPP
  • HPPA
  • Hydroxyphenylpyruvate
  • Hydroxyphenylpyruvic acid
  • p-hydroxyphenylpyruvic
  • p-hydroxyphenylpyruvic acid
  • Pyruvic acid, (p-hydroxyphenyl)-
  • 3-(4-HYDROXY-phenyl)pyruvate
  • 3-(p-Hydroxyphenyl)-2-oxopropanoate
  • 4-Hydroxy a-oxobenzenepropanoate
  • 4-Hydroxy a-oxobenzenepropanoic acid
  • 4-Hydroxy alpha-oxobenzenepropanoate
  • 4-Hydroxy α-oxobenzenepropanoate
  • 4-Hydroxy α-oxobenzenepropanoic acid
  • p-Hydroxyphenylpyruvate
  • Testacid
  • 4-Hydroxyphenylpyruvic acid, ion
  • 4-Hydroxyphenylpyruvic acid, sodium salt
  • Para-hydroxyphenylpyruvic acid
CAS number156-39-8
WeightAverage: 180.1574
Monoisotopic: 180.042258744
InChI KeyKKADPXVIOXHVKN-UHFFFAOYSA-N
InChIInChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
IUPAC Name3-(4-hydroxyphenyl)-2-oxopropanoic acid
Traditional IUPAC Name4-hydroxyphenylpyruvic acid
Chemical FormulaC9H8O4
SMILESOC(=O)C(=O)CC1=CC=C(O)C=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Phenylpyruvate
  • 3-phenylpropanoic-acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alpha-keto acid
  • Keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point219-220 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.49 g/LALOGPS
logP1.12ALOGPS
logP1.6ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.69 m³·mol⁻¹ChemAxon
Polarizability16.75 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • peroxisome
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Tyrosine metabolismPW002441 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Methane metabolismec00680 Map00680
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
Tyrosine metabolismec00350 Map00350
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB Reactions
(4-hydroxyphenyl)pyruvic acid + L-AlaninePyruvic acid + L-Tyrosine
(4-hydroxyphenyl)pyruvic acid + L-Glutamic acidOxoglutaric acid + L-Tyrosine
(4-hydroxyphenyl)pyruvic acid + hydron4-Hydroxyphenylacetaldehyde + Carbon dioxide
Prephenate + NADPNADPH + Carbon dioxide + (4-hydroxyphenyl)pyruvic acid
KEGG Reactions
NADH + (4-hydroxyphenyl)pyruvic acid + hydronNAD + 3-(4-hydroxyphenyl)lactic acid
NAD + PrephenateNADH + Carbon dioxide + (4-hydroxyphenyl)pyruvic acid
NADP + PrephenateCarbon dioxide + (4-hydroxyphenyl)pyruvic acid + NADPH
L-Glutamic acid + (4-hydroxyphenyl)pyruvic acidL-Tyrosine + Oxoglutaric acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • 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
  • Iraqui, I., Vissers, S., Cartiaux, M., Urrestarazu, A. (1998). "Characterisation of Saccharomyces cerevisiae ARO8 and ARO9 genes encoding aromatic aminotransferases I and II reveals a new aminotransferase subfamily." Mol Gen Genet 257:238-248.9491083
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15999
HMDB IDHMDB00707
Pubchem Compound ID979
Kegg IDC01179
ChemSpider ID954
FOODB IDFDB022193
Wikipedia4-Hydroxyphenylpyruvic_acid
BioCyc IDP-HYDROXY-PHENYLPYRUVATE

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Second most abundant of three pyruvate decarboxylases (PDC1, PDC5, PDC6) implicated in the nonoxidative conversion of pyruvate to acetaldehyde and carbon dioxide during alcoholic fermentation. Most of the produced acetaldehyde is subsequently reduced to ethanol, but some is required for cytosolic acetyl-CoA production for biosynthetic pathways. The enzyme is also one of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) able to decarboxylate more complex 2-oxo acids (alpha-keto-acids) than pyruvate, which seem mainly involved in amino acid catabolism. Here the enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids. In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids valine, isoleucine, phenylalanine, and tryptophan, whereas leucine is no substrate. In a side-reaction the carbanionic intermediate (or active aldehyde) generated by decarboxylation or by activation of an aldehyde can react with an aldehyde via condensation (or carboligation) yielding a 2-hydroxy ketone, collectively called acyloins
Gene Name:
PDC5
Uniprot ID:
P16467
Molecular weight:
61911.60156
Reactions
A 2-oxo acid → an aldehyde + CO(2).
3-(indol-3-yl)pyruvate → 2-(indol-3-yl)acetaldehyde + CO(2).
Phenylpyruvate → phenylacetaldehyde + CO(2).
Pyruvate → Acetaldehyde + CO(2).
A 2-oxo acid + an aldehyde → A 2-hydroxy ketone + CO(2).
An aldehyde + an aldehyde → A 2-hydroxy ketone.
General function:
Involved in magnesium ion binding
Specific function:
Minor of three pyruvate decarboxylases (PDC1, PDC5, PDC6) implicated in the nonoxidative conversion of pyruvate to acetaldehyde and carbon dioxide during alcoholic fermentation. Most of the produced acetaldehyde is subsequently reduced to ethanol, but some is required for cytosolic acetyl-CoA production for biosynthetic pathways. The enzyme is also one of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) able to decarboxylate more complex 2-oxo acids (alpha-keto-acids) than pyruvate, which seem mainly involved in amino acid catabolism. Here the enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids. In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids valine, isoleucine, phenylalanine, and tryptophan, whereas leucine is no substrate. In a side-reaction the carbanionic intermediate (or active aldehyde) generated by decarboxylation or by activation of an aldehyde can react with an aldehyde via condensation (or carboligation) yielding a 2-hydroxy ketone, collectively called acyloins. The expression level of this protein in the presence of fermentable carbon sources is so low that it can not compensate for the other two pyruvate decarboxylases to sustain fermentation
Gene Name:
PDC6
Uniprot ID:
P26263
Molecular weight:
61579.89844
Reactions
A 2-oxo acid → an aldehyde + CO(2).
3-(indol-3-yl)pyruvate → 2-(indol-3-yl)acetaldehyde + CO(2).
Phenylpyruvate → phenylacetaldehyde + CO(2).
Pyruvate → Acetaldehyde + CO(2).
A 2-oxo acid + an aldehyde → A 2-hydroxy ketone + CO(2).
An aldehyde + an aldehyde → A 2-hydroxy ketone.
General function:
Involved in magnesium ion binding
Specific function:
Major of three pyruvate decarboxylases (PDC1, PDC5, PDC6) implicated in the nonoxidative conversion of pyruvate to acetaldehyde and carbon dioxide during alcoholic fermentation. Most of the produced acetaldehyde is subsequently reduced to ethanol, but some is required for cytosolic acetyl-CoA production for biosynthetic pathways. The enzyme is also one of five 2-oxo acid decarboxylases (PDC1, PDC5, PDC6, ARO10, and THI3) able to decarboxylate more complex 2-oxo acids (alpha-ketoacids) than pyruvate, which seem mainly involved in amino acid catabolism. Here the enzyme catalyzes the decarboxylation of amino acids, which, in a first step, have been transaminated to the corresponding 2-oxo acids. In a third step, the resulting aldehydes are reduced to alcohols, collectively referred to as fusel oils or alcohols. Its preferred substrates are the transaminated amino acids valine, isoleucine, phenylalanine, and tryptophan, whereas leucine is no substrate. In a side-reaction the carbanionic intermediate (or active aldehyde) generated by decarboxylation or by activation of an aldehyde can react with an aldehyde via condensation (or carboligation) yielding a 2-hydroxy ketone, collectively called acyloins
Gene Name:
PDC1
Uniprot ID:
P06169
Molecular weight:
61494.89844
Reactions
A 2-oxo acid → an aldehyde + CO(2).
3-(indol-3-yl)pyruvate → 2-(indol-3-yl)acetaldehyde + CO(2).
Phenylpyruvate → phenylacetaldehyde + CO(2).
Pyruvate → Acetaldehyde + CO(2).
A 2-oxo acid + an aldehyde → A 2-hydroxy ketone + CO(2).
An aldehyde + an aldehyde → A 2-hydroxy ketone.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity and kynurenine aminotransferase activity
Gene Name:
ARO9
Uniprot ID:
P38840
Molecular weight:
58527.0
Reactions
An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity. Also active with methionine, alpha-aminoadipate and leucine when phenylpyruvate is the amino acceptor
Gene Name:
ARO8
Uniprot ID:
P53090
Molecular weight:
56177.30078
Reactions
An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
L-2-aminoadipate + 2-oxoglutarate → 2-oxoadipate + L-glutamate
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 transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol
Gene Name:
AAT1
Uniprot ID:
Q01802
Molecular weight:
51795.10156
Reactions
L-aspartate + 2-oxoglutarate → oxaloacetate + L-glutamate.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism
Gene Name:
AAT2
Uniprot ID:
P23542
Molecular weight:
46057.30078
Reactions
L-aspartate + 2-oxoglutarate → oxaloacetate + L-glutamate.