Identification

Name
Phenylpyruvic acid
Accession Number
DB03884  (EXPT02649)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
X7CO62M413
CAS number
156-06-9
Weight
Average: 164.158
Monoisotopic: 164.047344122
Chemical Formula
C9H8O3
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UL-phenylalanine dehydrogenaseNot AvailableRhodococcus sp.
UHydroxyacid oxidase 1Not AvailableHuman
UIndole-3-pyruvate decarboxylaseNot AvailableAzospirillum brasilense
UPutative uncharacterized proteinNot AvailableChromobacterium violaceum (strain ATCC 12472 / DSM 30191 / JCM 1249 / NBRC 12614 / NCIMB 9131 / NCTC 9757)
UBacilysin biosynthesis protein BacBNot AvailableBacillus subtilis (strain 168)
UProbable chorismate mutaseNot AvailableBifidobacterium 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
PhenylketonuriaDisease
Phenylalanine and Tyrosine MetabolismMetabolic
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)Disease
Tyrosinemia Type 3 (TYRO3)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00205
KEGG Compound
C00166
PubChem Compound
997
PubChem Substance
46506809
ChemSpider
972
ChEBI
30851
ChEMBL
CHEMBL1162488
HET
PPY
PDB Entries
1bw9 / 1lco / 2q5o / 2zf4 / 3h7j / 3h7y / 3h9a / 3luy / 4dqd / 4kic
show 2 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.932 mg/mLALOGPS
logP1.3ALOGPS
logP1.9ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)-9.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.71 m3·mol-1ChemAxon
Polarizability15.75 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9766
Blood Brain Barrier+0.9392
Caco-2 permeable+0.6174
P-glycoprotein substrateNon-substrate0.7968
P-glycoprotein inhibitor INon-inhibitor0.923
P-glycoprotein inhibitor IINon-inhibitor0.9587
Renal organic cation transporterNon-inhibitor0.911
CYP450 2C9 substrateNon-substrate0.8472
CYP450 2D6 substrateNon-substrate0.942
CYP450 3A4 substrateNon-substrate0.8014
CYP450 1A2 substrateNon-inhibitor0.9261
CYP450 2C9 inhibitorNon-inhibitor0.9569
CYP450 2D6 inhibitorNon-inhibitor0.9636
CYP450 2C19 inhibitorNon-inhibitor0.9673
CYP450 3A4 inhibitorNon-inhibitor0.9811
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9827
Ames testNon AMES toxic0.8852
CarcinogenicityNon-carcinogens0.7818
BiodegradationReady biodegradable0.915
Rat acute toxicity1.7408 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9751
hERG inhibition (predictor II)Non-inhibitor0.9729
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-00ko-9700000000-1a891469df1de787159b
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0006-1900000000-7dc1a5344d13e4dc19ac
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-001i-0900000000-bbbc84c54d03c4a14e51
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0a4i-0900000000-00b547b0371603520b61
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS; 1 MEOX)GC-MSsplash10-00di-9100000000-fdd48b632e63c8478078
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-000f-9300000000-8cd32f87e04ae0b6d6fb
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)GC-MSsplash10-014u-9720000000-7a0b66e6c18ff42ac05e
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0006-9760000000-d94111a7b9babceb265b
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00ko-9700000000-1a891469df1de787159b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9100000000-fdd48b632e63c8478078
GC-MS Spectrum - GC-MSGC-MSsplash10-000f-9300000000-8cd32f87e04ae0b6d6fb
GC-MS Spectrum - GC-MSGC-MSsplash10-014u-9720000000-7a0b66e6c18ff42ac05e
GC-MS Spectrum - GC-MSGC-MSsplash10-0006-9760000000-d94111a7b9babceb265b
GC-MS Spectrum - GC-MSGC-MSsplash10-000f-9300000000-8cd32f87e04ae0b6d6fb
GC-MS Spectrum - GC-MSGC-MSsplash10-014u-9720000000-7a0b66e6c18ff42ac05e
GC-MS Spectrum - GC-MSGC-MSsplash10-0006-9760000000-d94111a7b9babceb265b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00ko-9700000000-cec4a53271b8d66c2abc
Mass Spectrum (Electron Ionization)MSsplash10-00kf-9300000000-d1a7d23e7c5270b16883
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-066r-0900000000-ceb2ce23352e0f45ee33
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-004i-9200000000-ed4a6740d574858da982
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-004i-9000000000-c239a9a599daa607e47f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
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
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
2-oxo monocarboxylic acid (CHEBI:30851)

Targets

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
  1. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10592235]
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
  1. 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. [PubMed:10592235]
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
  1. 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. [PubMed:10592235]
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
  1. 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. [PubMed:10592235]
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
  1. 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. [PubMed:10592235]

Transporters

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11101640]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:34