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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

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:59 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.437   0.166   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.771   0.936   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.104   0.166   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.105  -1.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.771  -2.144   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.437  -1.374   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.103   0.936   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.230   0.166   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.230  -1.374   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.564   0.936   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.564   2.476   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.897   0.166   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

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

Adverse health effect

Genetic disorder

Inborn errors of metabolism

Phenylketonuria (PMID: 24023812 , PMID: 6321058 , PMID: 20971021 , +55

Source	Link
Pubmed	PMID: 24023812
Pubmed	PMID: 6321058
Pubmed	PMID: 20971021
Pubmed	PMID: 20573794
Pubmed	PMID: 23657156
Pubmed	PMID: 22800120
Pubmed	PMID: 21389975
Pubmed	PMID: 27012787
Pubmed	PMID: 9625050
Pubmed	PMID: 15740018
Pubmed	PMID: 12663291
Pubmed	PMID: 2702744
Pubmed	PMID: 16939360
Pubmed	PMID: 17474139
Pubmed	PMID: 15992788
Pubmed	PMID: 22827565
Pubmed	PMID: 22148915
Pubmed	PMID: 21388201
Pubmed	PMID: 22932811
Pubmed	PMID: 19551947
Pubmed	PMID: 31775291
Pubmed	PMID: 2026685
Pubmed	PMID: 4434100
Pubmed	PMID: 28853722
Pubmed	PMID: 19033659
Pubmed	PMID: 23430553
Pubmed	PMID: 3168222
Pubmed	PMID: 19468821
Pubmed	PMID: 31506554
Pubmed	PMID: 2116554
Pubmed	PMID: 19309105
Pubmed	PMID: 25536744
Pubmed	PMID: 4903899
Pubmed	PMID: 14708889
Pubmed	PMID: 8087979
Pubmed	PMID: 4837567
Pubmed	PMID: 2091926
Pubmed	PMID: 17022649
Pubmed	PMID: 32966057
Pubmed	PMID: 15651030
Pubmed	PMID: 24909877
Pubmed	PMID: 6790852
Pubmed	PMID: 4837567
Pubmed	PMID: 15168722
Pubmed	PMID: 7320149
Pubmed	PMID: 25012580
Pubmed	PMID: 25213569
Pubmed	PMID: 466810
Pubmed	PMID: 9686366
Pubmed	PMID: 25754623
Pubmed	PMID: 12101068
Pubmed	PMID: 19217890
Pubmed	PMID: 10102904
Pubmed	PMID: 9732980
Pubmed	PMID: 8178819
Pubmed	PMID: 16789974
Pubmed	PMID: 3873535
Pubmed	PMID: 30830347

)

Digestive system disorder

Hepatobiliary disorder

Biliary disorder

Primary biliary cirrhosis - Concentration is elevated compared to control group (PMID: 32966057 , PMID: 8216688 , PMID: 8216688 , +4

Source	Link
Pubmed	PMID: 32966057
Pubmed	PMID: 8216688
Pubmed	PMID: 8216688
Pubmed	PMID: 20671299
Pubmed	PMID: 2010161
Pubmed	PMID: 16807145
Pubmed	PMID: 2010161

)

Disposition

Biological location

Cellular substructure

Cytoplasm

Non-excretory biofluid

Blood

Excreta

Feces
Urine

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Phenylalanine and tyrosine metabolism

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.93 g/L	ALOGPS
logP	1.9	ChemAxon
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.395	31661259
DarkChem	[M+H]+	137.395	31661259
DarkChem	[M-H]-	134.795	31661259
DarkChem	[M-H]-	134.795	31661259
AllCCS	[M+H]+	134.365	32859911
AllCCS	[M-H]-	132.52	32859911
DeepCCS	[M+H]+	133.441	30932474
DeepCCS	[M-H]-	130.52	30932474
DeepCCS	[M-2H]-	167.0	30932474
DeepCCS	[M+Na]+	142.486	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylpyruvic acid	OC(=O)C(=O)CC1=CC=CC=C1	2649.3	Standard polar	33892256
Phenylpyruvic acid	OC(=O)C(=O)CC1=CC=CC=C1	1265.7	Standard non polar	33892256
Phenylpyruvic acid	OC(=O)C(=O)CC1=CC=CC=C1	1385.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylpyruvic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CC1=CC=CC=C1	1517.2	Semi standard non polar	33892256
Phenylpyruvic acid,1TMS,isomer #2	C[Si](C)(C)OC(=CC1=CC=CC=C1)C(=O)O	1669.7	Semi standard non polar	33892256
Phenylpyruvic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C	1615.5	Semi standard non polar	33892256
Phenylpyruvic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C	1695.2	Standard non polar	33892256
Phenylpyruvic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C	1898.4	Standard polar	33892256
Phenylpyruvic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CC1=CC=CC=C1	1747.9	Semi standard non polar	33892256
Phenylpyruvic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CC1=CC=CC=C1)C(=O)O	1924.3	Semi standard non polar	33892256
Phenylpyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	2099.9	Semi standard non polar	33892256
Phenylpyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	2101.6	Standard non polar	33892256
Phenylpyruvic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	2186.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-00ko-9700000000-1a891469df1de787159b	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0006-1900000000-7dc1a5344d13e4dc19ac	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001i-0900000000-bbbc84c54d03c4a14e51	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0a4i-0900000000-00b547b0371603520b61	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS; 1 MEOX)	splash10-00di-9100000000-fdd48b632e63c8478078	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-MS (1 MEOX; 1 TMS)	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-MS (1 MEOX; 1 TMS)	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-MS (2 TMS)	splash10-0006-9760000000-d94111a7b9babceb265b	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Non-derivatized)	splash10-00ko-9700000000-1a891469df1de787159b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Non-derivatized)	splash10-00di-9100000000-fdd48b632e63c8478078	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized)	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized)	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized)	splash10-0006-9760000000-d94111a7b9babceb265b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized)	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized)	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized)	splash10-0006-9760000000-d94111a7b9babceb265b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylpyruvic acid GC-EI-TOF (Non-derivatized)	splash10-00ko-9700000000-cec4a53271b8d66c2abc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-9a8a36c751256480752e	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00r6-9500000000-3e83cb905f1fd4362497	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpyruvic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kf-9300000000-d1a7d23e7c5270b16883	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpyruvic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-066r-0900000000-ceb2ce23352e0f45ee33	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpyruvic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-004i-9200000000-ed4a6740d574858da982	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpyruvic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-004i-9000000000-c239a9a599daa607e47f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpyruvic acid LC-ESI-QFT , negative-QTOF	splash10-014i-0900000000-36e00f6baa5d907e851b	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpyruvic acid LC-ESI-QTOF 35V, negative-QTOF	splash10-014i-0900000000-843a66173124c8fdf184	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpyruvic acid 35V, Negative-QTOF	splash10-014i-0900000000-272f6079d347e1b34e86	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 10V, Positive-QTOF	splash10-014j-1900000000-5d025096b1bb0e80dc1c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 20V, Positive-QTOF	splash10-014m-3900000000-9d0be907ecb6cc5efe8c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 40V, Positive-QTOF	splash10-0006-9200000000-a4fc563b3536eafc044d	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 10V, Negative-QTOF	splash10-03di-1900000000-0f660ae6dc074d939404	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 20V, Negative-QTOF	splash10-014j-1900000000-d229883bf098b04e0fcb	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 40V, Negative-QTOF	splash10-014i-5900000000-a107b725b71a6441a80c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 10V, Negative-QTOF	splash10-03xr-1900000000-8ba05dd4c5612aae9f50	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 20V, Negative-QTOF	splash10-0006-9300000000-946fa61c2a2596d7592d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 40V, Negative-QTOF	splash10-0006-9200000000-fa13a9bfbb6c03b2e12d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 10V, Positive-QTOF	splash10-014l-4900000000-2d56731d3ebcebf8079a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 20V, Positive-QTOF	splash10-0006-9200000000-9b3ae8fbf3992b1b2f28	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpyruvic acid 40V, Positive-QTOF	splash10-0006-9000000000-089373761153dce3ca74	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	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

Good Scents ID

Not Available

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

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 ]
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 ]
Lasala JM, Coscia CJ: Accumulation of a tetrahydroisoquinoline in phenylketonuria. Science. 1979 Jan 19;203(4377):283-4. [PubMed:153583 ]
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 ]
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)

MOL for HMDB0000205 (Phenylpyruvic acid)

3D MOL for HMDB0000205 (Phenylpyruvic acid)

3D SDF for HMDB0000205 (Phenylpyruvic acid)

3D-SDF for HMDB0000205 (Phenylpyruvic acid)

PDB for HMDB0000205 (Phenylpyruvic acid)

3D PDB for HMDB0000205 (Phenylpyruvic acid)

SMILES for HMDB0000205 (Phenylpyruvic acid)

INCHI for HMDB0000205 (Phenylpyruvic acid)

Structure for HMDB0000205 (Phenylpyruvic acid)

3D Structure for HMDB0000205 (Phenylpyruvic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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