Page last updated: 2024-09-20

phenylpyruvic acid

Description

phenylpyruvic acid: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

phenylpyruvate : A 2-oxo monocarboxylic acid anion resulting from deprotonation of the carboxy group of either keto- or enol-phenylpyruvic acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

keto-phenylpyruvic acid : A 2-oxo monocarboxylic acid that is 3-phenylpropanoic acid substituted by an oxo group at position 2. It is an intermediate metabolite in the phenylalanine pathway. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID997
CHEMBL ID1162488
CHEBI ID30851
SCHEMBL ID43235
MeSH IDM0099164

Synonyms (78)

Synonym
2-oxo-3-phenyl-propionic acid
2-oxo-3-phenylpropanoic acid
phenylbrenztraubensaeure
CHEBI:30851 ,
beta-phenylpyruvic acid
keto-phenylpyruvic acid
3-phenyl-2-oxopropanoic acid
alpha-oxo-benzenepropanoic acid
2-oxo-3-phenyl-propanoic acid
pyruvic acid, phenyl-
benzenepropanoic acid, .alpha.-oxo-
PPY ,
C00166
alpha-ketohydrocinnamic acid
phenylpyruvate
3-phenyl-2-oxopropanoate
156-06-9
phenylpyruvic acid
3-phenylpyruvic acid
DB03884
2-oxo-3-phenylpropionic acid
phenylpyruvic acid, 98%
7D5F143E-52E8-4FBB-87F1-0D4F96B4CA60
AC-116009
AKOS000161798
bdbm50167651
alpha-keto-dl-phenylalanine
P0154
b-phenylpyruvic acid
CHEMBL1162488
einecs 205-847-1
benzenepropanoic acid, alpha-oxo-
2-oxo-3-phenylpropanic acid
unii-x7co62m413
x7co62m413 ,
EN300-49247
tox21_301362
dtxcid9022281
NCGC00255726-01
cas-156-06-9
dtxsid1042281 ,
FT-0631855
alpha-keto-phenylalanine
fema no. 3892
2-oxo-3-phenylpropionic acid [fhfi]
.beta.-phenylpyruvic acid
phenylpyruvic acid [who-dd]
3-phenyl-2-oxo propionic acid
phenylpyroracemic acid
.alpha.-oxobenzenepropanoic acid
S6131
phenyl pyruvic acid
phenyl-pyruvic acid
SCHEMBL43235
Q-201562
mfcd00002589
4KIF
phenylpyruvic acid, purum, >=98.0% (t)
phenylpyruvic acid, analytical standard
sr-01000580517
SR-01000580517-1
beta-phenylpyruvate
fema 3892
a-oxobenzenepropanoic acid, 9ci
b-phenylpyruvate
a-hydroxycinnamic acid
alpha-ketohydrocinnamate
2-hydroxy-3-phenyl-2-propenoic acid, 9ci
phenylpyroracemate
HY-W012530
CS-W013246
Q425030
1R-0191
D91915
A883597
STARBLD0007879
SY040637
Z285151774

Research Excerpts

Overview

ExcerptReference
"Phenylpyruvic acid is a deaminated form of phenylalanine and is used in various areas such as development of cheese and wine flavors, diagnosis of phenylketonuria, and to decrease excessive nitrogen accumulation in the manure of farm animals. "( Coban, HB; Demirci, A; Elias, RJ; Patterson, PH, 2016)
"Phenylpyruvic acid (PPA) is an important organic acid that has a wide range of applications. "( Du, G; Hossain, GS; Hou, Y; Li, J; Liu, L; Shin, HD, 2015)

Roles (3)

RoleDescription
fundamental metaboliteAny metabolite produced by all living cells.
chromogenic compoundColourless, endogenous or exogenous pigment precursors that may be transformed by biological mechanisms into coloured compounds. They are used in biochemical assays and in diagnosis as indicators, particularly in the form of enzyme substrates.
EC 6.4.1.1 (pyruvate carboxylase) inhibitorAn EC 6.4.1.* (carboxylase) inhibitor that interferes with the action of pyruvate carboxylase (EC 6.4.1.1).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
2-oxo monocarboxylic acidAny monocarboxylic acid having a 2-oxo substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (14)

phenylpyruvic acid is involved in 14 pathway(s), involving a total of 77 unique proteins and 659 unique compounds

PathwayProteinsCompounds
Phenylalanine and Tyrosine Metabolism1121
Phenylketonuria1121
Tyrosinemia Type 2 (or Richner-Hanhart Syndrome)1121
Tyrosinemia Type 3 (TYRO3)1121
Phenylalanine Biosynthesis39
Phenylalanine Metabolism1013
Tropane, Piperidine, and Pyridine Alkaloid Biosynthesis617
Phenylalanine degradation ( Phenylalanine degradation )1314
2-Oxo-glutaric acid + L-Phenylalanine = L-Glutamic acid + Phenyl-pyruvic acid ( Phenylalanine degradation )14
Phenylalanine, tyrosine, and tryptophan biosynthesis012
phenylalanine biosynthesis06
Phenylalanine biosynthesis08
Tryptophan degradation07
Biochemical pathways: part I0466
Phenylalanine biosynthesis I08
Ehrlich pathway011

Protein Targets (10)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLI family zinc finger 3Homo sapiens (human)Potency47.94780.000714.592883.7951AID1259369; AID1259392
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency56.78100.001022.650876.6163AID1224838; AID1224893
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency10.96220.000214.376460.0339AID720691
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency68.58960.003041.611522,387.1992AID1159552; AID1159555
thyroid stimulating hormone receptorHomo sapiens (human)Potency28.45790.001628.015177.1139AID1224843; AID1224895
v-jun sarcoma virus 17 oncogene homolog (avian)Homo sapiens (human)Potency58.19650.057821.109761.2679AID1159528
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency27.30600.000627.21521,122.0200AID743202; AID743219
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier family 22 member 20Mus musculus (house mouse)Ki28.92011.10006.67899.1201AID360149
Solute carrier family 22 member 6Mus musculus (house mouse)Ki79.14430.40745.02179.4000AID360150; AID598880
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
positive regulation of transcription by RNA polymerase IIC-terminal-binding protein 2Homo sapiens (human)
positive regulation of retinoic acid receptor signaling pathwayC-terminal-binding protein 2Homo sapiens (human)
negative regulation of transcription by RNA polymerase IIC-terminal-binding protein 2Homo sapiens (human)
negative regulation of cell population proliferationC-terminal-binding protein 2Homo sapiens (human)
viral genome replicationC-terminal-binding protein 2Homo sapiens (human)
negative regulation of DNA-templated transcriptionC-terminal-binding protein 2Homo sapiens (human)
white fat cell differentiationC-terminal-binding protein 2Homo sapiens (human)
regulation of transcription by RNA polymerase IIC-terminal-binding protein 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
transcription corepressor bindingC-terminal-binding protein 2Homo sapiens (human)
transcription corepressor activityC-terminal-binding protein 2Homo sapiens (human)
protein bindingC-terminal-binding protein 2Homo sapiens (human)
oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptorC-terminal-binding protein 2Homo sapiens (human)
protein kinase bindingC-terminal-binding protein 2Homo sapiens (human)
protein-containing complex bindingC-terminal-binding protein 2Homo sapiens (human)
NAD bindingC-terminal-binding protein 2Homo sapiens (human)
DNA-binding transcription factor bindingC-terminal-binding protein 2Homo sapiens (human)
transcription coregulator bindingC-terminal-binding protein 2Homo sapiens (human)
transcription coactivator activityC-terminal-binding protein 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
nucleusC-terminal-binding protein 2Homo sapiens (human)
synapseC-terminal-binding protein 2Homo sapiens (human)
transcription repressor complexC-terminal-binding protein 2Homo sapiens (human)
nucleusC-terminal-binding protein 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2014Acta crystallographica. Section D, Biological crystallography, Jun, Volume: 70, Issue:Pt 6
Structure and mechanism of a nonhaem-iron SAM-dependent C-methyltransferase and its engineering to a hydratase and an O-methyltransferase.
AID360150Inhibition of mouse Oat1-mediated [3H]PAH uptake in Xenopus oocytes after 1 hr2007The Journal of biological chemistry, Aug-17, Volume: 282, Issue:33
Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members.
AID1453183Binding affinity to CK2alpha (unknown origin) assessed as change in melting temperature by thermal shift assay2017Bioorganic & medicinal chemistry, 07-01, Volume: 25, Issue:13
A fragment-based approach leading to the discovery of a novel binding site and the selective CK2 inhibitor CAM4066.
AID681140TP_TRANSPORTER: uptake in Xenopus laevis oocytes2000The Journal of physiology, Dec-01, Volume: 529 Pt 2Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle.
AID1130306Inhibition of glycolic acid oxidase (unknown origin) assessed as enzyme-mediated reduction of NaDCIP by sodium glycolate after 1 to 3 mins by spectrophotometer analysis1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Quantitative structure-activity relationships involving the inhibition of glycolic acid oxidase by derivatives of glycolic and glyoxylic acids.
AID360151Ratio of pKi for mouse Oat1 expressed in Xenopus oocytes to pKi for mouse Oat6 expressed in Xenopus oocytes2007The Journal of biological chemistry, Aug-17, Volume: 282, Issue:33
Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members.
AID1298930Inhibition of recombinant His6-tagged CtBP2 (31 to 384 residues) (unknown origin) dehydrogenase activity expressed in Escherichia coli BL21-Codonplus (DE3)-RIL cells using MTOB as substrate after 15 mins by NADH consumption assay2016Bioorganic & medicinal chemistry, 06-15, Volume: 24, Issue:12
Design, synthesis, and biological evaluation of substrate-competitive inhibitors of C-terminal Binding Protein (CtBP).
AID360149Inhibition of mouse Oat6-mediated [3H]ES uptake in Xenopus oocytes after 1 hr2007The Journal of biological chemistry, Aug-17, Volume: 282, Issue:33
Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members.
AID598880Inhibition of mouse Oat1 expressed in Xenopus oocytes2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Elucidation of common pharmacophores from analysis of targeted metabolites transported by the multispecific drug transporter-Organic anion transporter1 (Oat1).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (297)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990153 (51.52)18.7374
1990's34 (11.45)18.2507
2000's37 (12.46)29.6817
2010's55 (18.52)24.3611
2020's18 (6.06)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.32%)5.53%
Reviews6 (1.93%)6.00%
Case Studies2 (0.64%)4.05%
Observational0 (0.00%)0.25%
Other302 (97.11%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]