Record Information
Version1.0
Creation date2011-09-21 00:09:53 UTC
Update date2015-10-09 22:27:36 UTC
Primary IDFDB022193
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxyphenylpyruvic acid
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 (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. A deficiency in the catalytic activity of HPD is known to lead to tyrosinemia type III, an autosomal recessive disorder characterized by elevated levels of blood tyrosine and massive excretion of tyrosine derivatives into urine. It has been shown that hawkinsinuria, an autosomal dominant disorder characterized by the excretion of 'hawkinsin,' may also be a result of HPD deficiency (PMID: 11073718). [HMDB]
CAS Number156-39-8
Structure
Thumb
Synonyms
SynonymSource
(p-hydroxyphenyl)-Pyruvatehmdb
(p-hydroxyphenyl)-Pyruvic acidhmdb
(p-Hydroxyphenyl)pyruvatehmdb
(p-Hydroxyphenyl)pyruvic acidhmdb
3-(4-HYDROXY-phenyl)pyruvateGenerator
3-(4-HYDROXY-phenyl)pyruvIC ACIDChEBI
3-(4-hydroxyphenyl)-2-oxo-propanoatehmdb
3-(4-hydroxyphenyl)-2-oxo-propanoic acidhmdb
3-(4-Hydroxyphenyl)-2-oxopropionatehmdb
3-(4-Hydroxyphenyl)-2-oxopropionic acidhmdb
3-(4-Hydroxyphenyl)pyruvatehmdb
3-(4-Hydroxyphenyl)pyruvic acidhmdb
3-(P-Hydroxyphenyl)-2-oxopropanoateGenerator
3-(P-Hydroxyphenyl)-2-oxopropanoic acidChEBI
3-(p-Hydroxyphenyl)-2-oxopropionatehmdb
3-(p-Hydroxyphenyl)-2-oxopropionic acidhmdb
3-(p-Hydroxyphenyl)pyruvatehmdb
3-(p-Hydroxyphenyl)pyruvic acidhmdb
4-Hydroxy a-oxobenzenepropanoateGenerator
4-Hydroxy a-oxobenzenepropanoic acidGenerator
4-Hydroxy alpha-oxobenzenepropanoateGenerator
4-Hydroxy alpha-oxobenzenepropanoic acidChEBI
4-Hydroxy α-oxobenzenepropanoateGenerator
4-Hydroxy α-oxobenzenepropanoic acidGenerator
4-Hydroxy-a-oxobenzenepropanoatehmdb
4-Hydroxy-a-oxobenzenepropanoic acidhmdb
4-Hydroxy-alpha-oxobenzenepropanoatehmdb
4-Hydroxy-alpha-oxobenzenepropanoic acidhmdb
4-hydroxyphenylpyruvatehmdb
4HPPAhmdb
Hydroxyphenylpyruvatehmdb
Hydroxyphenylpyruvic acidhmdb
P-HydroxyphenylpyruvateGenerator
p-hydroxyphenylpyruvichmdb
P-Hydroxyphenylpyruvic acidChEBI
Testacidhmdb
Predicted Properties
PropertyValueSource
Water Solubility4.89 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.05 m³·mol⁻¹ChemAxon
Polarizability16.64 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H8O4
IUPAC name3-hydroxy-2-oxo-3-phenylpropanoic acid
InChI IdentifierInChI=1S/C9H8O4/c10-7(8(11)9(12)13)6-4-2-1-3-5-6/h1-5,7,10H,(H,12,13)
InChI KeyZHLWCBHWYUISFY-UHFFFAOYSA-N
Isomeric SMILESOC(C(=O)C(O)=O)C1=CC=CC=C1
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
Classification
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Phenylpyruvate
  • 3-phenylpropanoic-acid
  • Beta-hydroxy acid
  • Alpha-keto acid
  • Acyloin
  • Hydroxy acid
  • Keto acid
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9600000000-37e5789e9e75e065483cView in MoNA
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
ChemSpider ID954
ChEMBL IDCHEMBL607712
KEGG Compound IDC01179
Pubchem Compound ID979
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB07718
HMDB IDHMDB00707
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID37006
KNApSAcK IDNot Available
HET IDENO
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHydroxyphenylpyruvic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Tyrosine aminotransferaseTATP17735
Aspartate aminotransferase, cytoplasmicGOT1P17174
Aspartate aminotransferase, mitochondrialGOT2P00505
Macrophage migration inhibitory factorMIFP14174
Pathways
NameSMPDB LinkKEGG Link
Phenylalanine and Tyrosine MetabolismSMP00008 map00360
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference