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Identification
YMDB IDYMDB00151
Name4-Hydroxyphenylpyruvic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-Hydroxyphenylpyruvic acid, also known as 4-hydroxy a-oxobenzenepropanoate or (p-hydroxyphenyl)pyruvate, 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. 4-Hydroxyphenylpyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxyphenylpyruvic acid exists in all living species, ranging from bacteria to humans. 4-Hydroxyphenylpyruvic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (p-hydroxyphenyl)-Pyruvate
  • (p-hydroxyphenyl)-Pyruvic acid
  • (p-Hydroxyphenyl)pyruvate
  • (p-Hydroxyphenyl)pyruvic acid
  • 3-(4-hydroxyphenyl)-2-oxo-propanoate
  • 3-(4-hydroxyphenyl)-2-oxo-propanoic 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-oxopropionate
  • 3-(p-Hydroxyphenyl)-2-oxopropionic acid
  • 3-(p-Hydroxyphenyl)pyruvate
  • 3-(p-Hydroxyphenyl)pyruvic acid
  • 4-Hydroxy-a-oxobenzenepropanoate
  • 4-Hydroxy-a-oxobenzenepropanoic acid
  • 4-Hydroxy-alpha-oxobenzenepropanoate
  • 4-Hydroxy-alpha-oxobenzenepropanoic acid
  • 4-hydroxyphenylpyruvate
  • 4HPPA
  • HPPA
  • Hydroxyphenylpyruvate
  • Hydroxyphenylpyruvic acid
  • p-hydroxyphenylpyruvic
  • Testacid
  • 3-(4-HYDROXY-phenyl)pyruvIC ACID
  • 3-(p-Hydroxyphenyl)-2-oxopropanoic acid
  • 4-Hydroxy alpha-oxobenzenepropanoic acid
  • p-Hydroxyphenylpyruvic acid
  • 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
  • 4-Hydroxyphenylpyruvic acid, ion
  • 4-Hydroxyphenylpyruvic acid, sodium salt
  • Para-hydroxyphenylpyruvic acid
CAS number156-39-8
WeightAverage: 180.1574
Monoisotopic: 180.042258744
InChI KeyZHLWCBHWYUISFY-UHFFFAOYSA-N
InChIInChI=1S/C9H8O4/c10-7(8(11)9(12)13)6-4-2-1-3-5-6/h1-5,7,10H,(H,12,13)
IUPAC Name3-(4-hydroxyphenyl)-2-oxopropanoic acid
Traditional IUPAC Name4-hydroxyphenylpyruvic acid
Chemical FormulaC9H8O4
SMILES[H]OC(=O)C(=O)C([H])(O[H])C1=C([H])C([H])=C([H])C([H])=C1[H]
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
  • Cytoplasm, Mitochondrion, Peroxisome
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 ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-002f-1920000000-75b07d9c09371340939fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00xr-9340000000-087aad2497b3493d27c0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-002o-5910000000-fd1e55c84c79bfeca559JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-002f-1941000000-2b4c87544657895fcaf6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-014i-3492100000-483bdcea11d60fe4d306JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-014i-6791000000-ddc0a3b695cd1d0769f2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-1951000000-ecd071a64b26ca77684cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002f-1920000000-75b07d9c09371340939fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xr-9340000000-087aad2497b3493d27c0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-002o-5910000000-fd1e55c84c79bfeca559JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-002f-1941000000-2b4c87544657895fcaf6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-3492100000-483bdcea11d60fe4d306JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-6791000000-ddc0a3b695cd1d0769f2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-2920000000-469469dfaad745fa78e8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-002o-2910000000-4f336335a2366e7dd6dbJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6900000000-91bfe3ee54a36877251bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0adi-6961000000-670161f1542fda9ff1feJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0900000000-12033042c41b550bed42JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-0900000000-6e8a3701c6d254cc824dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0560-1900000000-8082c68e259d24234d05JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-2416d7f64101b9473cbbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-2900000000-b4c21b3d9751b9e56d67JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0005-9400000000-708e258e692a0abfbc92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9100000000-7d75e23ae6944c1e9c6dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001m-9000000000-fb80dcbab23323a042afJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-2416d7f64101b9473cbbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-2900000000-ad1f1fabdf6b1579fff7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0005-9400000000-708e258e692a0abfbc92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9100000000-7d75e23ae6944c1e9c6dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001m-9000000000-fb80dcbab23323a042afJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1900000000-76ae33b45e4348d50b07JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08gr-0900000000-be3cb913118057f499d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06rj-0900000000-6bebea0fda2ef3a2263bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-6900000000-ede11b81a97e891c66e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-2584f872c980915c1739JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01s9-1900000000-249c71cfa9cefe2a8020JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-3900000000-66991d861a91be9b9286JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0a59-5900000000-6c003e26816579df31caJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Braus, G. H. (1991). "Aromatic amino acid biosynthesis in the yeast Saccharomyces cerevisiae: a model system for the regulation of a eukaryotic biosynthetic pathway." Microbiol Rev 55:349-370.1943992
Synthesis Reference:Billek, Gerhard. p-Hydroxyphenylpyruvic acid. Organic Syntheses (1963), 43 49-54.
External Links:
ResourceLink
CHEBI ID15999
HMDB IDHMDB00707
Pubchem Compound ID979
Kegg IDC01179
ChemSpider ID11596439
FOODB IDFDB022193
Wikipedia4-Hydroxyphenylpyruvic_acid
BioCyc IDP-HYDROXY-PHENYLPYRUVATE

Enzymes

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.