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Bovine Rumen Metabolome Database



Showing metabocard for Phenylpyruvic acid (RMDB00205)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-10-28 14:42:01
Accession Number RMDB00205
Common Name Phenylpyruvic acid
Description Phenylpyruvic acid is a keto-acid that is an intermediate or catabolic byproduct of phenylalanine metabolism. It has a slight honey-like odor. Levels of phenylpyruvate are normally very low in blood or urine. High levels of phenylpyruvic acid can be found in the urine of individuals with phenylketonuria (PKU). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid. In particular, excessive phenylalanine can be metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation.
Synonyms
  1. 2-Oxo-3-phenylpropanoate
  2. 2-Oxo-3-phenylpropanoic acid
  3. 3-Phenyl-2-oxopropanoate
  4. 3-Phenyl-2-oxopropanoic acid
  5. 3-Phenylpyruvate
  6. 3-Phenylpyruvic acid
  7. Phenylpyroracemate
  8. Phenylpyroracemic acid
  9. Phenylpyruvate
  10. alpha-Ketohydrocinnamate
  11. alpha-Ketohydrocinnamic acid
  12. b-Phenylpyruvate
  13. b-Phenylpyruvic acid
  14. keto-Phenylpyruvate
  15. beta-Phenylpyruvate
  16. beta-Phenylpyruvic acid
Chemical IUPAC Name 2-oxo-3-phenyl-propanoic acid
Chemical Formula C9H8O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Aromatic Acids
Sub Class
  • Miscellaneous aromatic acids
Family
  • Mammalian_Metabolite
Species
  • ketone; carboxylic acid; aromatic compound
Biofunction
  • Component of Novobiocin biosynthesis; Component of Phenylalanine metabolism; Component of Phenylalanine, tyrosine and tryptophan biosynthesis; Component of Tyrosine metabolism
Application
Source
  • Endogenous
Average Molecular Weight 164.158
Monoisotopic Molecular Weight 164.047348
Isomeric SMILES OC(=O)C(=O)CC1=CC=CC=C1
Canonical SMILES OC(=O)C(=O)CC1=CC=CC=C1
KEGG Compound ID C00166 Link Image
BioCyc ID PHENYL-PYRUVATE Link Image
BiGG ID 34111 Link Image
Wikipedia Link Not Available
METLIN ID 328 Link Image
PubChem Compound 997 Link Image
PubChem Substance 7885109 Link Image
ChEBI ID 18005 Link Image
CAS Registry Number 156-06-9
InChI Identifier InChI=1/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)
Synthesis Reference Li, Hongbin; Luo, Yuzhong. Preparation of phenyl-pyruvic acid by dicarbonylation of benzyl halide. Faming Zhuanli Shenqing Gongkai Shuomingshu (1996), 5 pp.
Melting Point (Experimental) 154
Experimental Water Solubility 112 mg/mL [HMP experimental] Source: PhysProp
Predicted Water Solubility 0.932 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 1.30 [Predicted by ALOGPS]; 1.1 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 1LCO Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • mitochondria
Biofluid Location
  • Rumen
Tissue Location Not Available
Concentrations (Normal)
Biofluid Rumen
Value 16.7+/-13.5 uM
Age N/A
Sex Both
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available
Metabolic Enzymes
  1. Macrophage migration inhibitory factor
Enzyme 1 [top]
Enzyme 1 ID 123
Enzyme 1 Name Macrophage migration inhibitory factor
Enzyme 1 Synonyms
  1. MIF
  2. Phenylpyruvate tautomerase
  3. L-dopachrome tautomerase
  4. L-dopachrome isomerase
  5. p12A
Enzyme 1 Gene Name MIF
Enzyme 1 Protein Sequence >Macrophage migration inhibitory factor
MPMFVVNTNVPRASVPDGLLSELTQQLAQATGKPAQYIAVHVVPDQLMTFGGSSEPCALC
SLHSIGKIGGAQNRSYSKLLCGLLTERLRISPDRIYINFCDMNAANVGWNGSTFA
Enzyme 1 Number of Residues 115
Enzyme 1 Molecular Weight 12343.1
Enzyme 1 Theoretical pI 7.94
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Involved in cytokine activity
Enzyme 1 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
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 74353847 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P80177 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name MIF_BOVIN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >348 bp
ATGCCGATGTTCGTGGTGAACACCAACGTGCCCCGCGCCTCCGTGCCGGACGGGCTCCTC
TCCGAGCTCACGCAGCAGCTGGCGCAGGCCACGGGCAAGCCGGCACAGTACATCGCGGTG
CACGTGGTCCCAGACCAGCTCATGACCTTCGGGGGCTCCAGCGAGCCCTGCGCGCTCTGC
AGCCTGCACAGCATCGGCAAGATCGGCGGCGCGCAGAACCGCTCCTACAGCAAGCTGCTG
TGCGGCCTGCTGACCGAGCGCCTGCGCATTAGCCCGGACAGGATCTACATCAACTTCTGC
GACATGAACGCGGCCAACGTGGGCTGGAACGGCTCCACCTTCGCCTGA
Enzyme 1 GenBank Gene ID BC102066 Link Image
Enzyme 1 GeneCard ID MIF Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:2
Enzyme 1 Locus 22q11.23
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available