Identification
- Generic Name
- Phenylpyruvic acid
- DrugBank Accession Number
- DB03884
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Phenylpyruvic acid (DB03884)
- Weight
- Average: 164.158
Monoisotopic: 164.047344122 - Chemical Formula
- C9H8O3
- Synonyms
- 2-oxo-3-phenylpropanic acid
- 3-phenyl-2-oxopropanoate
- 3-phenyl-2-oxopropanoic acid
- 3-phenylpyruvic acid
- alpha-Ketohydrocinnamic acid
- keto-Phenylpyruvate
- keto-phenylpyruvic acid
- Phenylbrenztraubensäure
- Phenylpyruvate
- Phenylpyruvic acid
- α-oxo-benzenepropanoic acid
- β-phenylpyruvic acid
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UL-phenylalanine dehydrogenase Not Available Rhodococcus sp. UHydroxyacid oxidase 1 Not Available Humans UIndole-3-pyruvate decarboxylase Not Available Azospirillum brasilense UPutative uncharacterized protein Not Available Chromobacterium violaceum (strain ATCC 12472 / DSM 30191 / JCM 1249 / NBRC 12614 / NCIMB 9131 / NCTC 9757) UBacilysin biosynthesis protein BacB Not Available Bacillus subtilis (strain 168) UProbable chorismate mutase Not Available Bifidobacterium adolescentis (strain ATCC 15703 / DSM 20083 / NCTC 11814 / E194a) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Tyrosinemia Type 3 (TYRO3) Disease Phenylketonuria Disease Phenylalanine and Tyrosine Metabolism Metabolic Tyrosinemia Type 2 (or Richner-Hanhart Syndrome) Disease - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Calcium phenylpyruvate 7V9Q5UU79A 51828-93-4 BKMMOJVSLBZNTK-UHFFFAOYSA-L
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpyruvic acid derivatives. These 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
- Phenylpropanoic acids / Alpha-keto acids and derivatives / Alpha-hydroxy ketones / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- 3-phenylpropanoic-acid / Alpha-hydroxy ketone / Alpha-keto acid / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Keto acid / Ketone
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- 2-oxo monocarboxylic acid (CHEBI:30851)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- X7CO62M413
- CAS number
- 156-06-9
- InChI Key
- BTNMPGBKDVTSJY-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)
- IUPAC Name
- 2-oxo-3-phenylpropanoic acid
- SMILES
- OC(=O)C(=O)CC1=CC=CC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000205
- KEGG Compound
- C00166
- PubChem Compound
- 997
- PubChem Substance
- 46506809
- ChemSpider
- 972
- BindingDB
- 50167651
- ChEBI
- 30851
- ChEMBL
- CHEMBL1162488
- ZINC
- ZINC000000901485
- PDBe Ligand
- PPY
- Wikipedia
- Phenylpyruvic_acid
- PDB Entries
- 1bw9 / 1lco / 2q5o / 2zf4 / 3h7j / 3h7y / 3h9a / 3luy / 4dqd / 4kic … show 6 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Diabetic Nephropathy 1 4 Unknown Status Treatment Muscular Atrophy 1 3 Recruiting Supportive Care Nephrotic Syndrome 1 2, 3 Not Yet Recruiting Treatment Hemodialysis Treatment / Kidney Function 1 1, 2 Completed Basic Science Renal Insufficiency,Chronic 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral Drug delivery system Oral 0.105 g Tablet Oral 105.000 mg Tablet Oral 67.000 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.932 mg/mL 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 15.79 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9766 Blood Brain Barrier + 0.9392 Caco-2 permeable + 0.6174 P-glycoprotein substrate Non-substrate 0.7968 P-glycoprotein inhibitor I Non-inhibitor 0.923 P-glycoprotein inhibitor II Non-inhibitor 0.9587 Renal organic cation transporter Non-inhibitor 0.911 CYP450 2C9 substrate Non-substrate 0.8472 CYP450 2D6 substrate Non-substrate 0.942 CYP450 3A4 substrate Non-substrate 0.8014 CYP450 1A2 substrate Non-inhibitor 0.9261 CYP450 2C9 inhibitor Non-inhibitor 0.9569 CYP450 2D6 inhibitor Non-inhibitor 0.9636 CYP450 2C19 inhibitor Non-inhibitor 0.9673 CYP450 3A4 inhibitor Non-inhibitor 0.9811 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9827 Ames test Non AMES toxic 0.8852 Carcinogenicity Non-carcinogens 0.7818 Biodegradation Ready biodegradable 0.915 Rat acute toxicity 1.7408 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9751 hERG inhibition (predictor II) Non-inhibitor 0.9729
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 139.5574411 predictedDarkChem Lite v0.1.0 [M-H]- 139.3693411 predictedDarkChem Lite v0.1.0 [M-H]- 139.4163411 predictedDarkChem Lite v0.1.0 [M-H]- 139.4280411 predictedDarkChem Lite v0.1.0 [M-H]- 130.51959 predictedDeepCCS 1.0 (2019) [M+H]+ 140.4494411 predictedDarkChem Lite v0.1.0 [M+H]+ 139.4929411 predictedDarkChem Lite v0.1.0 [M+H]+ 140.3220411 predictedDarkChem Lite v0.1.0 [M+H]+ 141.0494411 predictedDarkChem Lite v0.1.0 [M+H]+ 133.44081 predictedDeepCCS 1.0 (2019) [M+Na]+ 139.3434411 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.3513411 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.1411411 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.5838411 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.4856 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Rhodococcus sp.
- Pharmacological action
- Unknown
- General Function
- Phenylalanine dehydrogenase activity
- Specific Function
- Catalyzes the reversible, NAD-dependent deamination of L-phenylalanine to phenyl pyruvate, ammonia and NADH.
- Gene Name
- pdh
- Uniprot ID
- Q59771
- Uniprot Name
- Phenylalanine dehydrogenase
- Molecular Weight
- 36608.615 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Very-long-chain-(s)-2-hydroxy-acid oxidase activity
- Specific Function
- Has 2-hydroxyacid oxidase activity. Most active on the 2-carbon substrate glycolate, but is also active on 2-hydroxy fatty acids, with high activity towards 2-hydroxy palmitate and 2-hydroxy octano...
- Gene Name
- HAO1
- Uniprot ID
- Q9UJM8
- Uniprot Name
- Hydroxyacid oxidase 1
- Molecular Weight
- 40923.945 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Azospirillum brasilense
- Pharmacological action
- Unknown
- General Function
- Thiamine pyrophosphate binding
- Specific Function
- Not Available
- Gene Name
- ipdC
- Uniprot ID
- P51852
- Uniprot Name
- Indole-3-pyruvate decarboxylase
- Molecular Weight
- 57979.97 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Chromobacterium violaceum (strain ATCC 12472 / DSM 30191 / JCM 1249 / NBRC 12614 / NCIMB 9131 / NCTC 9757)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- Not Available
- Gene Name
- Not Available
- Uniprot ID
- Q7NSZ5
- Uniprot Name
- Putative uncharacterized protein
- Molecular Weight
- 21777.22 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Bacillus subtilis (strain 168)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- Part of the bacABCDE operon responsible for the biosynthesis of bacilysin.
- Gene Name
- bacB
- Uniprot ID
- P39639
- Uniprot Name
- Bacilysin biosynthesis protein BacB
- Molecular Weight
- 26839.49 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Bifidobacterium adolescentis (strain ATCC 15703 / DSM 20083 / NCTC 11814 / E194a)
- Pharmacological action
- Unknown
- General Function
- Prephenate dehydratase activity
- Specific Function
- Not Available
- Gene Name
- pheA
- Uniprot ID
- A1A2B5
- Uniprot Name
- Probable chorismate mutase
- Molecular Weight
- 35784.095 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Symporter activity
- Specific Function
- Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine...
- Gene Name
- SLC16A3
- Uniprot ID
- O15427
- Uniprot Name
- Monocarboxylate transporter 4
- Molecular Weight
- 49468.9 Da
References
- Manning Fox JE, Meredith D, Halestrap AP: Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. J Physiol. 2000 Dec 1;529 Pt 2:285-93. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 16, 2020 21:12