4-Hydroxyphenylpyruvic acid (PAMDB000176)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000176
Identification
Name: 4-Hydroxyphenylpyruvic acid
Description:4-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 (KEGG). 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.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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-Hydroxy-α-oxobenzenepropanoate
  • 4-Hydroxy-α-oxobenzenepropanoic acid
  • 4-Hydroxyphenylpyruvate
  • 4-Hydroxyphenylpyruvic acid
  • 4HPPA
  • p-hydroxyphenylpyruvate
  • HPP
  • HPPA
  • Hydroxyphenylpyruvate
  • Hydroxyphenylpyruvic acid
  • P-Hydroxyphenylpyruvate
  • P-Hydroxyphenylpyruvic
  • P-Hydroxyphenylpyruvic acid
  • Testacid
Chemical Formula: C9H8O4
Average Molecular Weight: 180.1574
Monoisotopic Molecular Weight: 180.042258744
InChI Key: KKADPXVIOXHVKN-UHFFFAOYSA-N
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)
CAS number: 156-39-8
IUPAC Name:3-hydroxy-2-oxo-3-phenylpropanoic acid
Traditional IUPAC Name: HPPA
SMILES:OC(=O)C(=O)CC1=CC=C(O)C=C1
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as phenylpyruvic acid derivatives. These are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
Kingdom Organic compounds
Super ClassBenzenoids
Class Benzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct Parent Phenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Phenylpyruvate
  • 3-phenylpropanoic-acid
  • Beta-hydroxy acid
  • Monosaccharide
  • Keto acid
  • Hydroxy acid
  • Alpha-keto acid
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-1
Melting point: 219-220 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.89 mg/mLALOGPS
logP0.43ALOGPS
logP1.19ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.05 m3·mol-1ChemAxon
Polarizability16.64 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
alpha-Ketoglutarate + L-Tyrosine <> 4-Hydroxyphenylpyruvic acid + L-Glutamate
Prephenate + NAD <> 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADH + Hydrogen ion
Prephenate + NAD > 4-Hydroxyphenylpyruvic acid + Carbon dioxide + NADH
L-Tyrosine + Oxoglutaric acid <> 4-Hydroxyphenylpyruvic acid + L-Glutamate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06si-0900000000-acf034eefde53804e4acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-037a90063139ec62d81aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9700000000-7c443a10a7af2fd25766View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-0900000000-e34e03644f0b34007d85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0570-4900000000-32e0ef4141563f2be22cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-fab36414b8e14847b9bdView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Billek, Gerhard. p-Hydroxyphenylpyruvic acid. Organic Syntheses (1963), 43 49-54.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB00707
Pubchem Compound ID979
Kegg IDC01179
ChemSpider ID11596439
WikipediaHydroxyphenylpyruvic acid
BioCyc IDP-HYDROXY-PHENYLPYRUVATE
EcoCyc IDP-HYDROXY-PHENYLPYRUVATE