Showing metabocard for 4-Hydroxyphenylpyruvic acid (BMDB0000707)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:35:13 UTC
Update Date2020-05-21 16:28:47 UTC
BMDB IDBMDB0000707
Secondary Accession Numbers
  • BMDB00707
Metabolite Identification
Common Name4-Hydroxyphenylpyruvic acid
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 exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 4-Hydroxyphenylpyruvic acid exists in all living species, ranging from bacteria to humans. 4-Hydroxyphenylpyruvic acid is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(4-Hydroxyphenyl)pyruvic acidChEBI
(p-Hydroxyphenyl)pyruvic acidChEBI
3-(4-HYDROXY-phenyl)pyruvIC ACIDChEBI
3-(4-Hydroxyphenyl)pyruvic acidChEBI
3-(p-Hydroxyphenyl)-2-oxopropanoic acidChEBI
4-Hydroxy alpha-oxobenzenepropanoic acidChEBI
p-Hydroxyphenylpyruvic acidChEBI
4-HydroxyphenylpyruvateKegg
(4-Hydroxyphenyl)pyruvateGenerator
(p-Hydroxyphenyl)pyruvateGenerator
3-(4-HYDROXY-phenyl)pyruvateGenerator
3-(4-Hydroxyphenyl)pyruvateGenerator
3-(p-Hydroxyphenyl)-2-oxopropanoateGenerator
4-Hydroxy a-oxobenzenepropanoateGenerator
4-Hydroxy a-oxobenzenepropanoic acidGenerator
4-Hydroxy alpha-oxobenzenepropanoateGenerator
4-Hydroxy α-oxobenzenepropanoateGenerator
4-Hydroxy α-oxobenzenepropanoic acidGenerator
p-HydroxyphenylpyruvateGenerator
(p-Hydroxyphenyl)-pyruvateHMDB
(p-Hydroxyphenyl)-pyruvic acidHMDB
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-(p-Hydroxyphenyl)-2-oxopropionateHMDB
3-(p-Hydroxyphenyl)-2-oxopropionic acidHMDB
3-(p-Hydroxyphenyl)pyruvateHMDB
3-(p-Hydroxyphenyl)pyruvic acidHMDB
4-Hydroxy-a-oxobenzenepropanoateHMDB
4-Hydroxy-a-oxobenzenepropanoic acidHMDB
4-Hydroxy-alpha-oxobenzenepropanoateHMDB
4-Hydroxy-alpha-oxobenzenepropanoic acidHMDB
4HPPAHMDB
HPPAHMDB
HydroxyphenylpyruvateHMDB
Hydroxyphenylpyruvic acidHMDB
p-HydroxyphenylpyruvicHMDB
TestacidHMDB
4-Hydroxyphenylpyruvic acid, ionHMDB
4-Hydroxyphenylpyruvic acid, sodium saltHMDB
Para-hydroxyphenylpyruvic acidHMDB
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name3-(4-hydroxyphenyl)-2-oxopropanoic acid
Traditional Name4-hydroxyphenylpyruvic acid
CAS Registry Number156-39-8
SMILES
OC(=O)C(=O)CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
InChI KeyKKADPXVIOXHVKN-UHFFFAOYSA-N
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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Milk
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000707
DrugBank IDDB07718
Phenol Explorer Compound IDNot Available
FooDB IDFDB030506
KNApSAcK IDC00007512
Chemspider ID954
KEGG Compound IDC01179
BioCyc IDP-HYDROXY-PHENYLPYRUVATE
BiGG ID37006
Wikipedia Link4-Hydroxyphenylpyruvic_acid
METLIN ID5675
PubChem Compound979
PDB IDNot Available
ChEBI ID15999
References
Synthesis ReferenceBillek, Gerhard. p-Hydroxyphenylpyruvic acid. Organic Syntheses (1963), 43 49-54.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]

Enzymes

Enzyme Details
1. Macrophage migration inhibitory factor
General function:
Involved in cytokine activity
Specific function:
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity (By similarity).
Gene Name:
MIF
Uniprot ID:
P80177
Molecular weight:
12343.0
Reactions
4-Hydroxyphenylpyruvic acid → 2-Hydroxy-3-(4-hydroxyphenyl)propenoic aciddetails
Enzyme Details
2. 4-hydroxyphenylpyruvate dioxygenase
General function:
Amino acid transport and metabolism
Specific function:
Key enzyme in the degradation of tyrosine.
Gene Name:
HPD
Uniprot ID:
Q5EA20
Molecular weight:
44963.0
Reactions
4-Hydroxyphenylpyruvic acid + Oxygen → Homogentisic acid + Carbon dioxidedetails
Enzyme Details
3. Tyrosine aminotransferase
General function:
Amino acid transport and metabolism
Specific function:
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity for phenylalanine (By similarity).
Gene Name:
TAT
Uniprot ID:
Q58CZ9
Molecular weight:
49691.0
Reactions
L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + L-Glutamic aciddetails
Enzyme Details
4. Interleukin 4 induced 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
IL4I1
Uniprot ID:
F1N191
Molecular weight:
64479.0
Reactions
L-Tyrosine + Water + Oxygen → 4-Hydroxyphenylpyruvic acid + Ammonia + Hydrogen peroxidedetails