Human Metabolome Database: Showing metabocard for Phenylpyruvic acid (HMDB0000205)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

enzymes (8) Show 8 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-11-09 23:12:43 UTC

HMDB ID

HMDB0000205

Secondary Accession Numbers

HMDB0001237
HMDB00205
HMDB0031629
HMDB01237
HMDB31629

Metabolite Identification

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), an inborn error of metabolism. 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. Phenylpyruvic acid is also a microbial metabolite, it can be produced by Lactobacillus plantarum (PMID: 9687465 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Phenyl-2-oxopropanoate	ChEBI
3-Phenyl-2-oxopropanoic acid	ChEBI
3-Phenylpyruvic acid	ChEBI
alpha-Ketohydrocinnamic acid	ChEBI
alpha-Oxo-benzenepropanoic acid	ChEBI
beta-Phenylpyruvic acid	ChEBI
Keto-phenylpyruvate	ChEBI
Phenylbrenztraubensaeure	ChEBI
Phenylpyruvate	ChEBI
3-PHENYLPYRUVate	Generator
a-Ketohydrocinnamate	Generator
a-Ketohydrocinnamic acid	Generator
alpha-Ketohydrocinnamate	Generator
α-Ketohydrocinnamate	Generator
α-Ketohydrocinnamic acid	Generator
a-Oxo-benzenepropanoate	Generator
a-Oxo-benzenepropanoic acid	Generator
alpha-Oxo-benzenepropanoate	Generator
α-Oxo-benzenepropanoate	Generator
α-Oxo-benzenepropanoic acid	Generator
b-Phenylpyruvate	Generator
b-Phenylpyruvic acid	Generator
beta-Phenylpyruvate	Generator
β-Phenylpyruvate	Generator
β-Phenylpyruvic acid	Generator
keto-Phenylpyruvic acid	Generator
2-Oxo-3-phenylpropanoate	HMDB, KEGG
2-Oxo-3-phenylpropanoic acid	HMDB, Generator
a-Hydroxycinnamic acid	HMDB
FEMA 3892	HMDB
Phenylpyruvic acid	ChEBI
2-Oxo-3-phenylpropionic acid	HMDB
3-Phenyl-2-oxopropionic acid	HMDB
alpha-Oxobenzenepropanoic acid	HMDB
alpha-Oxobenzenepropionic acid	HMDB
α-Oxobenzenepropanoic acid	HMDB
α-Oxobenzenepropionic acid	HMDB

Chemical Formula

C₉H₈O₃

Average Molecular Weight

164.158

Monoisotopic Molecular Weight

164.047344122

IUPAC Name

2-oxo-3-phenylpropanoic acid

Traditional Name

phenylpyruvic acid

CAS Registry Number

156-06-9

SMILES

OC(=O)C(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)

InChI Key

BTNMPGBKDVTSJY-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpyruvic acid derivatives

Direct Parent

Phenylpyruvic acid derivatives

Alternative Parents

Substituents

Phenylpyruvate
3-phenylpropanoic-acid
Keto acid
Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:30851 )

Ontology

Physiological effect

Health effect:

Health condition:

Primary biliary cirrhosis

Disposition

Source:

Endogenous

Biological:

Microbe:

Lactobacillus

Biological location:

Biofluid and excreta:

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Phenylalanine and Tyrosine Metabolism

Role

Industrial application:

Food and nutrition:

Flavoring agent

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	154 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	112 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.93 g/L	ALOGPS
logP	1.3	ALOGPS
logP	1.9	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-9.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	42.71 m³·mol⁻¹	ChemAxon
Polarizability	15.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-00ko-9700000000-1a891469df1de787159b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0006-1900000000-7dc1a5344d13e4dc19ac	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001i-0900000000-bbbc84c54d03c4a14e51	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0900000000-00b547b0371603520b61	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS; 1 MEOX)	splash10-00di-9100000000-fdd48b632e63c8478078	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0006-9760000000-d94111a7b9babceb265b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ko-9700000000-1a891469df1de787159b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9100000000-fdd48b632e63c8478078	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-9760000000-d94111a7b9babceb265b	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-9760000000-d94111a7b9babceb265b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ko-9700000000-cec4a53271b8d66c2abc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-9a8a36c751256480752e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00r6-9500000000-3e83cb905f1fd4362497	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-066r-0900000000-ceb2ce23352e0f45ee33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9200000000-ed4a6740d574858da982	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-c239a9a599daa607e47f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-014i-0900000000-36e00f6baa5d907e851b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-014i-0900000000-843a66173124c8fdf184	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-1900000000-5d025096b1bb0e80dc1c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014m-3900000000-9d0be907ecb6cc5efe8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-a4fc563b3536eafc044d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-0f660ae6dc074d939404	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-1900000000-d229883bf098b04e0fcb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-5900000000-a107b725b71a6441a80c	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kf-9300000000-d1a7d23e7c5270b16883	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phenylalanine and Tyrosine Metabolism
Phenylketonuria		Not Available
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)		Not Available
Tyrosinemia Type 3 (TYRO3)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.5 +/- 0.1 uM	Adult (>18 years old)	Both	Normal	8216688	details
Blood	Detected and Quantified	5 uM	Children (1 - 13 years old)	Both	Normal	6790852	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.17 (0.05-0.67) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	9869358	details
Urine	Detected and Quantified	0.24 (0.10-0.76) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9869358	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.00064 +/- 0.000544 umol/mmol creatinine	Newborn (0-30 days old)	Not Specified	Normal	7320149	details
Urine	Detected and Quantified	<2 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0.138 +/- 0.207 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	0.207 +/- 0.275 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	0.207 +/- 0.344 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	0.25 +/- 0.43 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	50.0 (40.0-60.0) uM	Newborn (0-30 days old)	Both	Phenylketonuria	6790852	details
Blood	Detected and Quantified	1.4 +/- 0.2 uM	Adult (>18 years old)	Both	Primary biliary cirrhosis	8216688	details
Urine	Detected and Quantified	7796.386 umol/mmol creatinine	Infant (0-1 year old)	Male	Phenylketonuria	15168722	details
Urine	Detected and Quantified	31047.8 umol/mmol creatinine	Children (1 - 13 years old)	Male	Phenylketonuria	15168722	details
Urine	Detected and Quantified	255.518 +/- 250.00780 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	735.560 +/- 528.253 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	882.948 +/- 741.0699 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	146.6 +/- 244.6 umol/mmol creatinine	Newborn (0-30 days old)	Both	Phenylketonuria	2091926	details

Associated Disorders and Diseases

Disease References

Phenylketonuria
Langenbeck U, Behbehani A, Luthe H: Renal transport of aromatic acids in patients with phenylketonuria. J Inherit Metab Dis. 1981;4(2):69-70. [PubMed:6790852 ] Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ] Swarna M, Jyothy A, Usha Rani P, Reddy PP: Amino acid disorders in mental retardation: a two-decade study from Andhra Pradesh. Biochem Genet. 2004 Apr;42(3-4):85-98. [PubMed:15168722 ] Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ] G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Primary biliary cirrhosis
Turchany JM, Leung PS, Iwayama T, Jefferson DM, Ishida J, Yamaguchi M, Munoz S, Danner DJ, Dickson ER, Gershwin ME: Comparative metabolism and structure of BCKD-E2 in primary biliary cirrhosis. J Autoimmun. 1993 Aug;6(4):459-66. [PubMed:8216688 ]

Associated OMIM IDs

261600 (Phenylketonuria)
109720 (Primary biliary cirrhosis)

External Links

DrugBank ID

DB03884

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30851

Food Biomarker Ontology

Not Available

VMH ID

PHPYR

MarkerDB ID

MDB00000098

References

Synthesis Reference

Li, Hongbin; Luo, Yuzhong. Preparation of phenyl-pyruvic acid by dicarbonylation of benzyl halide. Faming Zhuanli Shenqing Gongkai Shuomingshu (1996), 5 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Lasala JM, Coscia CJ: Accumulation of a tetrahydroisoquinoline in phenylketonuria. Science. 1979 Jan 19;203(4377):283-4. [PubMed:153583 ]
Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
Cassidei L, Dell'atti A, Sciacovelli O: Improvement of the FeCl3 test for phenylpyruvic acid. Clin Chim Acta. 1978 Dec 1;90(2):121-7. [PubMed:719897 ]
Michals K, Matalon R: Phenylalanine metabolites, attention span and hyperactivity. Am J Clin Nutr. 1985 Aug;42(2):361-5. [PubMed:4025205 ]
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
Nakahara T, Ishida J, Yamaguchi M, Nakamura M: Determination of alpha-keto acids including phenylpyruvic acid in human plasma by high-performance liquid chromatography with chemiluminescence detection. Anal Biochem. 1990 Nov 1;190(2):309-13. [PubMed:2291475 ]
Nierop Groot MN, de Bont JAM: Conversion of phenylalanine to benzaldehyde initiated by an aminotransferase in lactobacillus plantarum Appl Environ Microbiol. 1998 Aug;64(8):3009-13. [PubMed:9687465 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. Macrophage migration inhibitory factor

General function:: Involved in cell surface binding
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.
Gene Name:: MIF
Uniprot ID:: P14174
Molecular weight:: 12476.19

Reactions

Phenylpyruvic acid → Enol-phenylpyruvate	details
Phenylpyruvic acid → Enol-phenylpyruvate	details

Enzyme Details

2. Tyrosine aminotransferase

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
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 towards phenylalanine.
Gene Name:: TAT
Uniprot ID:: P17735
Molecular weight:: 50398.895

Reactions

L-Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + L-Glutamic acid	details

Enzyme Details

3. Aspartate aminotransferase, cytoplasmic

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Plays a key role in amino acid metabolism (By similarity).
Gene Name:: GOT1
Uniprot ID:: P17174
Molecular weight:: 46247.14

Reactions

L-Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + L-Glutamic acid	details

Enzyme Details

4. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:: GOT2
Uniprot ID:: P00505
Molecular weight:: 47517.285

Reactions

L-Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + L-Glutamic acid	details

Enzyme Details

5. Kynurenine--oxoglutarate transaminase 1

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:: CCBL1
Uniprot ID:: Q16773
Molecular weight:: 47874.765

Reactions

L-Glutamine + Phenylpyruvic acid → 2-Keto-glutaramic acid + L-Phenylalanine	details

Enzyme Details

6. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Phenylpyruvic acid → 3,4,5-trihydroxy-6-[(2-oxo-3-phenylpropanoyl)oxy]oxane-2-carboxylic acid	details

Enzyme Details

7. 4-hydroxyphenylpyruvate dioxygenase

General function:: Involved in 4-hydroxyphenylpyruvate dioxygenase activity
Specific function:: Key enzyme in the degradation of tyrosine.
Gene Name:: HPD
Uniprot ID:: P32754
Molecular weight:: 40497.105

Reactions

Phenylpyruvic acid + Oxygen → ortho-Hydroxyphenylacetic acid + Carbon dioxide	details

Enzyme Details

8. L-amino-acid oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name:: IL4I1
Uniprot ID:: Q96RQ9
Molecular weight:: 65327.26

Reactions

L-Phenylalanine + Water + Oxygen → Phenylpyruvic acid + Ammonia + Hydrogen peroxide	details

Showing metabocard for Phenylpyruvic acid (HMDB0000205)

Structure for HMDB0000205 (Phenylpyruvic acid)

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions