MiMeDB: Showing metabocard for Phenylpyruvic acid (MMDBc0029479)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:23:57 UTC

Update Date

2024-09-29 09:57:39 UTC

Metabolite ID

MMDBc0029479

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. Phenylalanine is converted 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.

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

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

Molecular Formula

C₉H₈O₃

Average Mass

164.158

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View 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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0006-9760000000-d94111a7b9babceb265b	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ko-9700000000-1a891469df1de787159b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9100000000-fdd48b632e63c8478078	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-9760000000-d94111a7b9babceb265b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000f-9300000000-8cd32f87e04ae0b6d6fb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014u-9720000000-7a0b66e6c18ff42ac05e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-9760000000-d94111a7b9babceb265b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ko-9700000000-cec4a53271b8d66c2abc	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-9a8a36c751256480752e	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00r6-9500000000-3e83cb905f1fd4362497	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-066r-0900000000-ceb2ce23352e0f45ee33	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9200000000-ed4a6740d574858da982	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-c239a9a599daa607e47f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-014i-0900000000-36e00f6baa5d907e851b	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-014i-0900000000-843a66173124c8fdf184	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-272f6079d347e1b34e86	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-1900000000-5d025096b1bb0e80dc1c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014m-3900000000-9d0be907ecb6cc5efe8c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-a4fc563b3536eafc044d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-0f660ae6dc074d939404	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-1900000000-d229883bf098b04e0fcb	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-5900000000-a107b725b71a6441a80c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-1900000000-8ba05dd4c5612aae9f50	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9300000000-946fa61c2a2596d7592d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-fa13a9bfbb6c03b2e12d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014l-4900000000-2d56731d3ebcebf8079a	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9200000000-9b3ae8fbf3992b1b2f28	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-089373761153dce3ca74	2021-09-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kf-9300000000-d1a7d23e7c5270b16883	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)		2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191773	Macrophage migration inhibitory factor	Enzyme	P14174	Homo sapiens
MMDBp0191947	Tyrosine aminotransferase	Enzyme	P17735	Homo sapiens
MMDBp0191953	Aspartate aminotransferase, cytoplasmic	Enzyme	P17174	Homo sapiens
MMDBp0191954	Aspartate aminotransferase, mitochondrial	Enzyme	P00505	Homo sapiens
MMDBp0192123	Kynurenine--oxoglutarate transaminase 1	Enzyme	Q16773	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0192461	4-hydroxyphenylpyruvate dioxygenase	Unknown	P32754	Homo sapiens
MMDBp0195052	L-amino-acid oxidase	Unknown	Q96RQ9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001933	Oxoglutaric acid	L-Glutamic acid	glutamic-oxaloacetic transaminase 2, mitochondrial	VMH; KEGG	30371894
MMDBr0001982	Phenylpyruvic acid	ortho-Hydroxyphenylacetic acid	Not Available	VMH; KEGG	30371894
MMDBr0005719	Phenyllactic acid	Phenylpyruvic acid	Not Available	VMH	30371894
MMDBr0007134	Prephenate	Phenylpyruvic acid	Not Available	VMH	30371894
MMDBr0007939	Oxoglutaric acid	L-Glutamic acid	Not Available	VMH; KEGG	30371894
MMDBr0008222	D-Phenyllactic acid	Phenylpyruvic acid	Not Available	VMH	30371894
MMDBr0010406	Phenylpyruvic acid	Enol-phenylpyruvate	macrophage migration inhibitory factor (glycosylation-inhibiting factor)	VMH; KEGG	30371894

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012748	L-Phenylalanine	Phenylpyruvic acid	Not Available			9687465
MMDBr0012749	Phenylpyruvic acid	Phenylacetic acid	Not Available			9687465

Reaction ID	Precursor	Product	Enzyme	Reference
MMDBr0012748	L-Phenylalanine	Phenylpyruvic acid	Not Available	9687465
MMDBr0012750	Phenylpyruvic acid	D-Phenyllactic acid	Not Available	Manually annotated by MiMeDB team
MMDBr0012754	D-Phenyllactic acid	Phenylacetic acid	Not Available	Manually annotated by MiMeDB team

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012748	L-Phenylalanine	Phenylpyruvic acid	Not Available			9687465
MMDBr0012751	Phenylpyruvic acid	2-Phenylpropionate	Not Available			Manually annotated by MiMeDB team

Reaction ID	Precursor	Product	Enzyme	Reference
MMDBr0012748	L-Phenylalanine	Phenylpyruvic acid	Not Available	9687465
MMDBr0012750	Phenylpyruvic acid	D-Phenyllactic acid	Not Available	Manually annotated by MiMeDB team
MMDBr0012755	D-Phenyllactic acid	2-Phenylpropionate	Not Available	Manually annotated by MiMeDB team

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Phenylketonuria		Association	Human Urine	HMDB	15168722
Phenylketonuria		Association	Human Urine	HMDB	2091926
Phenylketonuria		Association	Human Urine	HMDB	4837567
Phenylketonuria		Association	Human Blood	HMDB	6790852
Primary biliary cirrhosis	Increased	Association	Human Blood	HMDB	8216688
Primary biliary cirrhosis		Association	Human plasma	PubMed	8216688
Phenylketonuria		Association	Human urine	PubMed	15168722

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	199	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	387	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	127	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	115	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	5	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	5	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food	Sake	Rice	KNApSAcK	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.25	0.43			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Urine	Detected and Quantified	146.6	244.6			umol/mmol creatinine	Newborn (0-30 days old)	Both	Phenylketonuria	HMDB	2091926
Human Urine	Detected and Quantified	0.207	0.344			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	735.56	528.253			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified	0.138	0.207			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	882.948	741.0699			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified	0.207	0.275			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	255.518	250.0078			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Blood	Detected and Quantified	5				uM	Children (1 - 13 years old)	Both	Normal	HMDB	6790852
Human Blood	Detected and Quantified	50		40	60	uM	Newborn (0-30 days old)	Both	Phenylketonuria	HMDB	6790852
Human Urine	Detected and Quantified	0.00064	0.000544			umol/mmol creatinine	Newborn (0-30 days old)	Not Specified	Normal	HMDB	7320149
Human Blood	Detected and Quantified	0.5	0.1			uM	Adult (>18 years old)	Both	Normal	HMDB	8216688
Human Blood	Detected and Quantified	1.4	0.2			uM	Adult (>18 years old)	Both	Primary biliary cirrhosis	HMDB	8216688
Human Urine	Detected and Quantified	0.24		0.1	0.76	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	9869358
Human Urine	Detected and Quantified	0.17		0.05	0.67	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	9869358
Human Urine	Detected and Quantified	7796.386				umol/mmol creatinine	Infant (0-1 year old)	Male	Phenylketonuria	HMDB	15168722
Human Urine	Detected and Quantified	31047.8				umol/mmol creatinine	Children (1 - 13 years old)	Male	Phenylketonuria	HMDB	15168722
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected and Quantified	7796.386				umol/mmol creatinine	Infant (0-1 year old)	Male	Phenylketonuria	HMDB	15168722
Human Urine	Detected and Quantified	31047.8				umol/mmol creatinine	Children (1 - 13 years old)	Male	Phenylketonuria	HMDB	15168722
Human Urine	Detected and Quantified	146.6	244.6			umol/mmol creatinine	Newborn (0-30 days old)	Both	Phenylketonuria	HMDB	2091926
Human Urine	Detected and Quantified	255.518	250.00780			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Blood	Detected and Quantified	50.0		40.0	60.0	uM	Newborn (0-30 days old)	Both	Phenylketonuria	HMDB	6790852
Human Urine	Detected and Quantified	735.560	528.253			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified	882.948	741.0699			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Blood	Detected and Quantified	1.4	0.2			uM	Adult (>18 years old)	Both	Primary biliary cirrhosis	HMDB	8216688
Human Blood	Detected and Quantified	5				uM	Children (1 - 13 years old)	Both	Normal	HMDB	6790852
Human Urine	Detected and Quantified	0.00064	0.000544			umol/mmol creatinine	Newborn (0-30 days old)	Not Specified	Normal	HMDB	7320149
Human Urine	Detected and Quantified	0.138	0.207			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	0.17		0.05	0.67	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	9869358
Human Urine	Detected and Quantified	0.207	0.275			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	0.207	0.344			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	0.24		0.10	0.76	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	9869358
Human Urine	Detected and Quantified	0.25	0.43			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Blood	Detected and Quantified	0.5	0.1			uM	Adult (>18 years old)	Both	Normal	HMDB	8216688
Human Urine	Detected and Quantified	<2				umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000205

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

References

Synthesis Reference

Not Available

General References

Lasala JM, Coscia CJ: Accumulation of a tetrahydroisoquinoline in phenylketonuria. Science. 1979 Jan 19;203(4377):283-4. doi: 10.1126/science.153583. [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. doi: 10.1016/0009-8981(78)90513-2. [PubMed:719897 ]
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. doi: 10.1016/0378-4347(91)80571-s. [PubMed:2026685 ]
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. doi: 10.1016/0003-2697(90)90199-j. [PubMed:2291475 ]
Michals K, Matalon R: Phenylalanine metabolites, attention span and hyperactivity. Am J Clin Nutr. 1985 Aug;42(2):361-5. doi: 10.1093/ajcn/42.2.361. [PubMed:4025205 ]
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. doi: 10.1128/AEM.64.8.3009-3013.1998. [PubMed:9687465 ]
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. doi: 10.1016/s0378-4347(98)00388-0. [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. doi: 10.1515/CCLM.2003.248. [PubMed:14708889 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Phenylpyruvic acid (MMDBc0029479)

MOL for #<Metabolite:0x00007f46e03d26c8>

3D MOL for #<Metabolite:0x00007f46e03d26c8>

3D SDF for #<Metabolite:0x00007f46e03d26c8>

3D-SDF for #<Metabolite:0x00007f46e03d26c8>

PDB for #<Metabolite:0x00007f46e03d26c8>

3D PDB for #<Metabolite:0x00007f46e03d26c8>

SMILES for #<Metabolite:0x00007f46e03d26c8>

INCHI for #<Metabolite:0x00007f46e03d26c8>

Structure for #<Metabolite:0x00007f46e03d26c8>

3D Structure for #<Metabolite:0x00007f46e03d26c8>