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MetaCyc Compound: 4-hydroxyphenylpyruvate

Synonyms: p-hydroxyphenylpyruvic acid, 3-(4-hydroxyphenyl)pyruvate, hydroxyphenylpyruvate, p-hydroxyphenylpyruvate

Superclasses: an acid all carboxy acids a carboxylate a 2-oxo acid an aromatic oxo-acid
an acid all carboxy acids a carboxylate an aromatic oxo-acid

Chemical Formula: C9H7O4

Molecular Weight: 179.15 Daltons

Monoisotopic Molecular Weight: 180.0422587452 Daltons

4-hydroxyphenylpyruvate compound structure

SMILES: C1(C(CC(C([O-])=O)=O)=CC=C(C=1)O)

InChI: InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)/p-1

InChIKey: InChIKey=KKADPXVIOXHVKN-UHFFFAOYSA-M

Unification Links: CAS:156-39-8 , ChEBI:36242 , ChemSpider:5341947 , HMDB:HMDB00707 , IAF1260:37006 , KEGG:C01179 , MetaboLights:MTBLC36242 , PubChem:6971070

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -43.714226 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

(S)-reticuline biosynthesis I , L-tyrosine degradation III :
4-hydroxyphenylpyruvate + H+ → CO2 + (4-hydroxyphenyl)acetaldehyde

3-dimethylallyl-4-hydroxybenzoate biosynthesis :
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate → 3-dimethylallyl-4-hydroxyphenylpyruvate + diphosphate

3-hydroxy-L-homotyrosine biosynthesis :
4-hydroxyphenylpyruvate + acetyl-CoA + H2O → 2-(4-hydroxybenzyl)-malate + coenzyme A + H+

4-hydroxybenzoate biosynthesis I (eukaryotes) :
3-(4-hydroxyphenyl)lactate + NAD+4-hydroxyphenylpyruvate + NADH + H+

atromentin biosynthesis :
2 4-hydroxyphenylpyruvate + 2 ATP → atromentin + 2 AMP + 2 diphosphate

factor 420 biosynthesis :
5-amino-6-(D-ribitylamino)uracil + 4-hydroxyphenylpyruvate + 2 S-adenosyl-L-methionine + H2O → 7,8-didemethyl-8-hydroxy-5-deazariboflavin + 2 5'-deoxyadenosine + 2 L-methionine + oxalate + ammonium + 3 H+

L-phenylalanine biosynthesis III (cytosolic, plants) , L-tyrosine degradation I , plastoquinol-9 biosynthesis I , vitamin E biosynthesis (tocopherols) :
4-hydroxyphenylpyruvate + oxygen → CO2 + homogentisate

L-tyrosine degradation II , L-tyrosine degradation IV (to 4-methylphenol) :
2 4-hydroxyphenylpyruvate + oxygen → 2 4-hydroxyphenylacetate + 2 CO2

rosmarinic acid biosynthesis I :
4-hydroxyphenylpyruvate + NAD(P)H + H+ → (R)-3-(4-hydroxyphenyl)lactate + NAD(P)+

Not in pathways:
4-hydroxyphenylpyruvate + oxygen → 4-hydroxymandelate + CO2

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

3-dimethylallyl-4-hydroxybenzoate biosynthesis , L-tyrosine biosynthesis I :
prephenate + NAD+4-hydroxyphenylpyruvate + CO2 + NADH

Not in pathways:
L-tyrosine + H2O + oxygen → 4-hydroxyphenylpyruvate + ammonium + hydrogen peroxide

3-hydroxy-L-homotyrosine biosynthesis :
4-(4-hydroxyphenyl)-2-oxobutanoate + an amino acid → L-homotyrosine + a 2-oxo acid

prodigiosin biosynthesis :
(S)-3-acetyloctanal + an L-amino acid → 2-methyl-3-n-amyl-dihydropyrrole + a 2-oxo acid + H2O

3,3'-thiodipropanoate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+

Not in pathways:
a 1-acyl 2-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a β-monogalactosyldiacylglycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

(S)-reticuline biosynthesis I , 4-hydroxybenzoate biosynthesis I (eukaryotes) , 4-hydroxyphenylpyruvate biosynthesis , atromentin biosynthesis , L-tyrosine biosynthesis I , L-tyrosine degradation I , L-tyrosine degradation II , L-tyrosine degradation IV (to 4-methylphenol) , rosmarinic acid biosynthesis I :
L-tyrosine + 2-oxoglutarate ↔ 4-hydroxyphenylpyruvate + L-glutamate

L-phenylalanine biosynthesis III (cytosolic, plants) :
2-oxo-3-phenylpropanoate + L-tyrosine ↔ L-phenylalanine + 4-hydroxyphenylpyruvate

L-tyrosine degradation III :
L-tyrosine + pyruvate ↔ 4-hydroxyphenylpyruvate + L-alanine
L-tyrosine + 2-oxoglutarate ↔ 4-hydroxyphenylpyruvate + L-glutamate

Not in pathways:
glyoxylate + an aromatic amino acid ↔ glycine + an aromatic oxo-acid
an aromatic amino acid + 2-oxoglutarate ↔ an aromatic oxo-acid + L-glutamate

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
prephenate + NADP+ = 4-hydroxyphenylpyruvate + CO2 + NADPH

Not in pathways:
an (R)-2-hydroxyacid + an electron-transfer quinone = a 2-oxo acid + an electron-transfer quinol

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

Enzymes inhibited by 4-hydroxyphenylpyruvate, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: 4-coumaroyl-CoA:R(+)-3,4-dihydroxyphenyllactate 2'-O-coumaroyl-transferase [Petersen91]

This compound has been characterized as an alternative substrate of the following enzymes: phenylalanine transaminase , imidazol-pyruvate reductase , aspartate aminotransferase , L-phenylalanine:2-oxoglutarate aminotransferase , L-tryptophan:phenylpyruvate aminotransferas


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Petersen91: Petersen M (1991). "Characterization of rosmarinic acid synthase from cell cultures of Coleus blumei." Phytochemistry, 30(9), 2877-2881.


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Mon Aug 31, 2015, biocyc14.