Record Information
Version 1.0
Update Date 1/22/2018 12:54:53 PM
Metabolite IDPAMDB000102
Identification
Name: Pyruvic acid
Description:Pyruvic acid is an alpha-keto acid. It can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through acetyl-CoA. It can also be used to construct the amino acid alanine and be converted into ethanol. Pyruvic acid supplies energy to living cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactic acid when oxygen is lacking (fermentation).
Structure
Thumb
Synonyms:
  • α-ketopropionate
  • α-ketopropionic acid
  • 2-Oxo-propionate
  • 2-Oxo-propionic acid
  • 2-Oxopropanoate
  • 2-Oxopropanoic acid
  • 2-Oxopropionate
  • 2-Oxopropionic acid
  • A-Ketopropionate
  • A-Ketopropionic acid
  • Acetylformate
  • Acetylformic acid
  • Alpha-Ketopropionate
  • Alpha-Ketopropionic acid
  • BTS
  • Pyroracemate
  • Pyroracemic acid
  • Pyruvate
  • Pyruvic acid
  • α-Ketopropionate
  • α-Ketopropionic acid
Chemical Formula: C3H4O3
Average Molecular Weight: 88.0621
Monoisotopic Molecular Weight: 88.016043994
InChI Key: LCTONWCANYUPML-UHFFFAOYSA-N
InChI:InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
CAS number: 127-17-3
IUPAC Name:2-oxopropanoic acid
Traditional IUPAC Name: pyruvic acid
SMILES:CC(=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Keto acids and derivatives
Sub ClassAlpha-keto acids and derivatives
Direct Parent Alpha-keto acids and derivatives
Alternative Parents
Substituents
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:-1
Melting point: 13.8 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000.0 mg/ml [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-0.517PhysProp
Predicted Properties
PropertyValueSource
Water Solubility134.0 mg/mLALOGPS
logP-0.38ALOGPS
logP0.066ChemAxon
logS0.18ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.99 m3·mol-1ChemAxon
Polarizability7.31 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Coenzyme A + 2 flavodoxin semi oxidized + Pyruvic acid <> Acetyl-CoA + Carbon dioxide +2 Flavodoxin reduced + Hydrogen ion
Coenzyme A + Pyruvic acid <> Acetyl-CoA + Formic acid
Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acid
Phosphoenolpyruvic acid + D-Glucose > Glucose 6-phosphate + Pyruvic acid
2-Ketobutyric acid + Hydrogen ion + Pyruvic acid > 2-Aceto-2-hydroxy-butyrate + Carbon dioxide
Hydrogen ion + 2 Pyruvic acid > (S)-2-Acetolactate + Carbon dioxide
Coenzyme A + NAD + Pyruvic acid > Acetyl-CoA + Carbon dioxide + NADH
Phosphoenolpyruvic acid + 2(alpha-D-Mannosyl)-D-glycerate > 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Pyruvic acid
L-Alanine + Pyridoxal 5'-phosphate > Pyridoxamine 5'-phosphate + Pyruvic acid
Dihydroxyacetone + Phosphoenolpyruvic acid > Dihydroxyacetone phosphate + Pyruvic acid
Chorismate + L-Glutamine <> 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acid
L-Cystathionine + Water > L-Homocysteine + Ammonium + Pyruvic acid
Phosphoenolpyruvic acid + D-Mannose > Mannose 6-phosphate + Pyruvic acid
Phosphoenolpyruvic acid + D-Fructose > Fructose 6-phosphate + Pyruvic acid
Phosphoenolpyruvic acid + N-Acetylmannosamine > N-Acetyl-D-mannosamine 6-phosphate + Pyruvic acid
Phosphoenolpyruvic acid + Glucosamine > Glucosamine 6-phosphate + Pyruvic acid
ADP + Hydrogen ion + Phosphoenolpyruvic acid <> Adenosine triphosphate + Pyruvic acid
Phosphoenolpyruvic acid + Galactitol > Galactitol 1-phosphate + Pyruvic acid
D-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acid
Phosphoenolpyruvic acid + D-Fructose > Fructose 1-phosphate + Pyruvic acid
alpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid
Phosphoenolpyruvic acid + Sorbitol > Pyruvic acid + Sorbitol-6-phosphate
Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid
Phosphoenolpyruvic acid + D-Maltose > Maltose 6'-phosphate + Pyruvic acid
Phosphoenolpyruvic acid + Trehalose > Pyruvic acid + Trehalose 6-phosphate
Phosphoenolpyruvic acid + Sucrose > Pyruvic acid + Sucrose-6-phosphate
Phosphoenolpyruvic acid + N-Acetyl-D-muramoate > N-Acetylmuramic acid 6-phosphate + Pyruvic acid
D-Alanine + Pyridoxal 5'-phosphate > Pyridoxamine 5'-phosphate + Pyruvic acid
Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acid
L-Lactic acid + Ubiquinone-8 > Pyruvic acid + Ubiquinol-8
L-Lactic acid + Menaquinone 8 > Menaquinol 8 + Pyruvic acid
L-Cysteine + Water > Hydrogen sulfide + Ammonium + Pyruvic acid
L-Serine > Ammonium + Pyruvic acid
Methylisocitric acid <> Pyruvic acid + Succinic acid
4-Hydroxy-2-oxopentanoate > Acetaldehyde + Pyruvic acid
D-Glyceraldehyde 3-phosphate + Hydrogen ion + Pyruvic acid <> Carbon dioxide + 1-Deoxy-D-xylulose 5-phosphate
Water + Isochorismate <> (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + Pyruvic acid
Water + Pyruvic acid + Ubiquinone-8 > Acetic acid + Carbon dioxide + Ubiquinol-8
4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Hydrogen ion + Pyruvic acid
D-Alanine + FAD + Water > FADH2 + Ammonium + Pyruvic acid
L-Malic acid + NAD > Carbon dioxide + NADH + Pyruvic acid
Adenosine triphosphate + Water + Pyruvic acid <> Adenosine monophosphate +2 Hydrogen ion + Phosphoenolpyruvic acid + Phosphate
(R)-Malate + NAD <> Carbon dioxide + NADH + Pyruvic acid
2-Keto-3-deoxy-6-phosphogluconic acid <> D-Glyceraldehyde 3-phosphate + Pyruvic acid
Hydrogen ion + Oxalacetic acid > Carbon dioxide + Pyruvic acid
D-Cysteine + Water > Hydrogen sulfide + Ammonium + Pyruvic acid
D-Lactic acid + Ubiquinone-8 > Pyruvic acid + Ubiquinol-8
2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate <> (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid
D-Serine > Ammonium + Pyruvic acid
Phosphoenolpyruvic acid + Chitobiose > Diacetylchitobiose-6-phosphate + Pyruvic acid
L-Malic acid + NADP > Carbon dioxide + NADPH + Pyruvic acid
Hydrogen cyanide + 3-Mercaptopyruvic acid + Cyanide <> Hydrogen ion + Pyruvic acid + Thiocyanate
5-Dehydro-4-deoxy-D-glucarate > Tartronate semialdehyde + Pyruvic acid
N-Acetylneuraminic acid + N-acetylneuraminate <> N-Acetylmannosamine + Pyruvic acid
alpha-Ketoisovaleric acid + L-Alanine <> Pyruvic acid + L-Valine + a-Ketoisovaleric acid
Water + L-Tryptophan <> Indole + Ammonium + Pyruvic acid
Chorismate <> 4-Hydroxybenzoic acid + Pyruvic acid
2-Acetolactate + Carbon dioxide <>2 Pyruvic acid
L-Lactic acid + 2 Ferricytochrome c + Ferricytochrome c <> Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ion + Ferrocytochrome c
Adenosine triphosphate + Pyruvic acid + Water <> Adenosine monophosphate + Phosphoenolpyruvic acid + Phosphate
Adenosine triphosphate + Pyruvic acid <> ADP + Phosphoenolpyruvic acid
Pyruvaldehyde + NAD + Water <> Pyruvic acid + NADH + Hydrogen ion
L-Malic acid + NAD <> Pyruvic acid + Carbon dioxide + NADH + Hydrogen ion
(R)-Malate + NAD <> Pyruvic acid + Carbon dioxide + NADH + Hydrogen ion
L-Malic acid + NADP <> Pyruvic acid + Carbon dioxide + NADPH + Hydrogen ion
L-Serine <> Pyruvic acid + Ammonia
D-Serine <> Pyruvic acid + Ammonia
(S)-2-Acetolactate + Carbon dioxide <>2 Pyruvic acid
Guanosine triphosphate + Pyruvic acid <> Guanosine diphosphate + Phosphoenolpyruvic acid
4-Hydroxy-2-oxoglutaric acid <> Pyruvic acid + Glyoxylic acid
D-4-Hydroxy-2-oxoglutarate <> Pyruvic acid + Glyoxylic acid
L-Tryptophan + Water <> Indole + Pyruvic acid + Ammonia
L-Cysteine + Water <> Hydrogen sulfide + Pyruvic acid + Ammonia
Chorismate + Ammonia <> 2-Aminobenzoic acid + Pyruvic acid + Water
Chorismate + L-Glutamine <> 2-Aminobenzoic acid + Pyruvic acid + L-Glutamate
dATP + Pyruvic acid <> dADP + Phosphoenolpyruvic acid
2 Reduced ferredoxin + Acetyl-CoA + Carbon dioxide + 2 Hydrogen ion + Oxidized ferredoxin <>2 Oxidized ferredoxin + Pyruvic acid + Coenzyme A + Reduced ferredoxin
L-Valine + Pyruvic acid <> alpha-Ketoisovaleric acid + L-Alanine
Cystathionine + Water <> L-Homocysteine + Ammonia + Pyruvic acid
L-Cystathionine + Water <> L-Homocysteine + Ammonia + Pyruvic acid
Pyruvic acid + Enzyme N6-(lipoyl)lysine <> [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Carbon dioxide + [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine
N-Acetylneuraminic acid <> N-Acetylmannosamine + Pyruvic acid
dGTP + Pyruvic acid <> dGDP + Phosphoenolpyruvic acid
D-Cysteine + Water <> Hydrogen sulfide + Ammonia + Pyruvic acid
2-Dehydro-3-deoxy-L-rhamnonate <> Lactaldehyde + Pyruvic acid + (S)-Lactaldehyde
L-Aspartate-semialdehyde + Pyruvic acid <> 2,3-Dihydrodipicolinic acid +2 Water
Nucleoside triphosphate + Pyruvic acid <> NDP + Phosphoenolpyruvic acid
3-Mercaptopyruvic acid + Sulfite <> Thiosulfate + Pyruvic acid
Hydrogen cyanide + 3-Mercaptopyruvic acid <> Thiocyanate + Pyruvic acid
Pyruvic acid + Ubiquinone-1 + Water <> Acetic acid + Ubiquinol-8 + Carbon dioxide
Tartronate semialdehyde + Pyruvic acid <> 2-Dehydro-3-deoxy-D-glucarate
Selenocystathionine + Water <> Selenohomocysteine + Ammonia + Pyruvic acid
Propanal + Pyruvic acid <> 4-Hydroxy-2-oxohexanoic acid
4-Amino-4-deoxychorismate <> p-Aminobenzoic acid + Pyruvic acid
Pyruvic acid + D-Glyceraldehyde 3-phosphate <> 1-Deoxy-D-xylulose 5-phosphate + Carbon dioxide
Pyruvic acid + 2-Ketobutyric acid <> 2-Aceto-2-hydroxy-butyrate + Carbon dioxide
Se-Methylselenocysteine + Water <> Pyruvic acid + Ammonia + Methaneselenol
an oxidized electron acceptor + L-Lactic acid > a reduced electron acceptor + Pyruvic acid
Pyruvic acid + hydroxylamine > pyruvic oxime + Water
Hydrogen ion + Pyruvic acid + Acetaldehyde > acetoin + Carbon dioxide
Hydrogen ion + 3-Mercaptopyruvic acid > Pyruvic acid + Hydrogen sulfide
Phosphoenolpyruvic acid + b-D-Glucose > Glucose 6-phosphate + Pyruvic acid
2,3-diaminopropanoate + Water > Hydrogen ion + Ammonia + Pyruvic acid
L-Serine > Hydrogen ion + Pyruvic acid + Ammonia
Hydrogen ion + Pyruvic acid <> (<i>S</i>)-2-acetolactate + Carbon dioxide
Oxoglutaric acid + L-Alanine <> L-Glutamate + Pyruvic acid
L-Cystathionine + Water > Hydrogen ion + Pyruvic acid + Ammonia + L-Homocysteine
an electron-transfer-related quinone + Water + D-Alanine > an electron-transfer-related quinol + Ammonium + Pyruvic acid
D-Cysteine + Water <> Pyruvic acid + Hydrogen sulfide + Ammonia + Hydrogen ion
2-Dehydro-3-deoxy-D-galactonate-6-phosphate <> D-Glyceraldehyde 3-phosphate + Pyruvic acid
2-Keto-3-deoxy-D-gluconic acid D-Glyceraldehyde + Pyruvic acid
Pyruvic acid + L-Aspartate-semialdehyde <> Hydrogen ion + Water + 2,3-Dihydrodipicolinic acid
an electron-transfer-related quinone + D-Lactic acid > an electron-transfer-related quinol + Pyruvic acid
D-Serine > Hydrogen ion + Pyruvic acid + Ammonia
L-Cysteine + Water > Pyruvic acid + Ammonia + Hydrogen sulfide + Hydrogen ion
Hydrogen cyanide + 3-Mercaptopyruvic acid Hydrogen ion + Pyruvic acid + Thiocyanate
Hydrogen ion + Pyruvic acid + Lipoamide S-Acetyldihydrolipoamide + Carbon dioxide
Pyruvic acid + Water + a ubiquinone > Carbon dioxide + a ubiquinol + Acetic acid
Phosphoenolpyruvic acid + <i>N</i>-acetylmuramate > N-Acetylmuramic acid 6-phosphate + Pyruvic acid
Pyruvic acid + Hydrogen ion > L-Lactic acid
2-keto-3-deoxy-L-rhamnonate Pyruvic acid + Lactaldehyde
Acetic acid + Carbon dioxide + Hydrogen ion <> Pyruvic acid + Water
Phosphoenolpyruvic acid + Salicin > Salicin 6-phosphate + Pyruvic acid
Phosphoenolpyruvic acid + Cellobiose > Cellobiose-6-phosphate + Pyruvic acid
D-fructose + Phosphoenolpyruvic acid > Fructose 1-phosphate + Pyruvic acid
D-fructose + Phosphoenolpyruvic acid > Fructose 6-phosphate + Pyruvic acid
L-Tryptophan + Water <> Hydrogen ion + Indole + Pyruvic acid + Ammonia
L-Valine + Pyruvic acid > a-Ketoisovaleric acid + L-Alanine
2-Dehydro-3-deoxy-D-galactonate 6-phosphate > Pyruvic acid + D-Glyceraldehyde 3-phosphate
Phosphoenolpyruvic acid + protein L-histidine > Pyruvic acid + protein N(pi)-phospho-L-histidine
D-Lactic acid + NAD > Pyruvic acid + NADH
L-Lactic acid + 2 Ferricytochrome c > Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ion
N-acetylneuraminate > N-Acetylmannosamine + Pyruvic acid
Pyruvic acid + [dihydrolipoyllysine-residue acetyltransferase] lipoyllysine > [dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Carbon dioxide
Pyruvic acid + Ubiquinone-10 + Water > Acetic acid + Carbon dioxide + Ubiquinol-1
Adenosine triphosphate + Pyruvic acid + Water > Adenosine monophosphate + Phosphoenolpyruvic acid + Inorganic phosphate
2-Dehydro-3-deoxy-L-rhamnonate > Pyruvic acid + D-Lactaldehyde
Pyruvic acid + L-Aspartate-semialdehyde <> (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + Water
L-Cystathionine + Water + 2-Aminoacrylic acid + 2-Iminopropanoate <> L-Homocysteine + Pyruvic acid + Ammonia
L-Serine + 2-Aminoacrylic acid + 2-Iminopropanoate + Water <> Pyruvic acid + Ammonia
D-Serine + 2-Aminoacrylic acid + 2-Iminopropanoate + Water <> Pyruvic acid + Ammonia
Phosphoenolpyruvic acid + Protein histidine <> Pyruvic acid + Protein N(pi)-phospho-L-histidine
2,3-Diaminopropanoate + Water <> Pyruvic acid +2 Ammonia
L-Tryptophan + Water + 2-Aminoacrylic acid + 2-Iminopropanoate <> Indole + Pyruvic acid + Ammonia
L-Malic acid + NAD + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADH
L-Malic acid + NADP + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADPH
D-Glyceraldehyde 3-phosphate + Pyruvic acid + Hydrogen ion + D-Glyceraldehyde 3-phosphate > 1-Deoxy-D-xylulose 5-phosphate + Carbon dioxide + 1-Deoxy-D-xylulose 5-phosphate
Water + isochorismate + Isochorismate > Pyruvic acid + 2,3-dihydroxy-2,3-dihydrobenzoate
L-Aspartate-semialdehyde + Pyruvic acid > Hydrogen ion + Water + (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate
Adenosine triphosphate + Pyruvic acid + Hydrogen carbonate > Adenosine diphosphate + Phosphate + Oxalacetic acid + ADP
L-Alanine + Oxoglutaric acid + L-Alanine <> L-Glutamic acid + Pyruvic acid + L-Glutamate
L-Alanine + Glyoxylic acid + L-Alanine <> Glycine + Pyruvic acid
Phosphoenolpyruvic acid + Adenosine diphosphate + Hydrogen ion + ADP > Adenosine triphosphate + Pyruvic acid
L-Valine + Pyruvic acid + L-Valine > L-Alanine + a-Ketoisovaleric acid + L-Alanine
D-Alanine + Water + Quinone > Ammonium + Pyruvic acid + Hydroquinone
D-Alanine + Water + an electron-transfer quinone > Ammonium + Pyruvic acid + electron-transfer quinol
5-dehydro-4-deoxy-D-glucarate(2?? > Pyruvic acid + Tartronate semialdehyde
Chorismate + L-Glutamine > L-Glutamic acid + Pyruvic acid + Hydrogen ion + 2-Aminobenzoic acid + L-Glutamate
L-Malic acid + NADP + L-Malic acid > Carbon dioxide + NADPH + Pyruvic acid + NADPH
L-Malic acid + NAD + L-Malic acid > Carbon dioxide + NADH + Pyruvic acid
2-dehydro-3-deoxy-D-galactonate 6-phosphate + 2-Dehydro-3-deoxy-D-galactonate 6-phosphate > Pyruvic acid + D-Glyceraldehyde 3-phosphate + D-Glyceraldehyde 3-phosphate
L-Lactic acid + oxidized electron acceptor + L-Lactic acid > Reduced acceptor + Pyruvic acid
2-Keto-3-deoxy-6-phosphogluconic acid > D-Glyceraldehyde 3-phosphate + Pyruvic acid + D-Glyceraldehyde 3-phosphate
4-amino-4-deoxychorismate + 4-Amino-4-deoxychorismate > Pyruvic acid + Hydrogen ion + p-Aminobenzoic acid
4-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoate > Pyruvic acid + Acetaldehyde
2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate > (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate + Pyruvic acid + (1R,6R)-6-Hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00dr-4900000000-f26ef76666e40ab9fe61View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-00di-5900000000-b8e81f82572d4796e944View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-5970000000-154bf9ad168a12593fccView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-a2cf85a5e1d2379d26dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-dd49835da8355fb6e625View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-f09d8e3d7a774b255d89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-7d91f6f626cab1a366fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-8ae98cdb3e142034e52aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-e04e6c68013983e1b6dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f315d0752893e7d0c657View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Elling D, Bader K: [Biochemical changes in cervix mucus in stepwise malignant transformation of cervix epithelium] Zentralbl Gynakol. 1990;112(9):555-60. Pubmed: 2378186
  • Foster KJ, Alberti KG, Hinks L, Lloyd B, Postle A, Smythe P, Turnell DC, Walton R: Blood intermediary metabolite and insulin concentrations after an overnight fast: reference ranges for adults, and interrelations. Clin Chem. 1978 Sep;24(9):1568-72. Pubmed: 688619
  • Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
  • Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
  • Ka T, Yamamoto T, Moriwaki Y, Kaya M, Tsujita J, Takahashi S, Tsutsumi Z, Fukuchi M, Hada T: Effect of exercise and beer on the plasma concentration and urinary excretion of purine bases. J Rheumatol. 2003 May;30(5):1036-42. Pubmed: 12734903
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Meijer-Severs GJ, Van Santen E, Meijer BC: Short-chain fatty acid and organic acid concentrations in feces of healthy human volunteers and their correlations with anaerobe cultural counts during systemic ceftriaxone administration. Scand J Gastroenterol. 1990 Jul;25(7):698-704. Pubmed: 2396083
  • Mongan PD, Capacchione J, West S, Karaian J, Dubois D, Keneally R, Sharma P: Pyruvate improves redox status and decreases indicators of hepatic apoptosis during hemorrhagic shock in swine. Am J Physiol Heart Circ Physiol. 2002 Oct;283(4):H1634-44. Epub 2002 Jun 20. Pubmed: 12234818
  • Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
  • Nielsen J, Ytrebo LM, Borud O: Lactate and pyruvate concentrations in capillary blood from newborns. Acta Paediatr. 1994 Sep;83(9):920-2. Pubmed: 7819686
  • Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530.
  • Reece PA, Cozamanis I, Zacest R: Selective high-performance liquid chromatographic assays for hydralazine and its metabolites in plasma of man. J Chromatogr. 1980 Mar 14;181(3-4):427-40. Pubmed: 7391156
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. Pubmed: 15627241
  • Talseth T, Haegele KD, McNay JL, Skrdlant HB, Clementi WA, Shepherd AM: Pharmacokinetics and cardiovascular effects in rabbits of a major hydralazine metabolite, the hydralazine pyruvic-acid hydrazone. J Pharmacol Exp Ther. 1979 Dec;211(3):509-13. Pubmed: 512915
  • Tsuchiya H, Hashizume I, Tokunaga T, Tatsumi M, Takagi N, Hayashi T: High-performance liquid chromatography of alpha-keto acids in human saliva. Arch Oral Biol. 1983;28(11):989-92. Pubmed: 6581765
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834
Synthesis Reference: Xiang, Wei; Okita, Motomu. Preparation of pyruvic acid. Jpn. Kokai Tokkyo Koho (2003), 5 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID15361
HMDB IDHMDB00243
Pubchem Compound ID1060
Kegg IDC00022
ChemSpider ID1031
WikipediaPyruvic acid
BioCyc IDPYRUVATE
EcoCyc IDPYRUVATE
Ligand ExpoPYR

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvI
Locus Tag:
PA4696
Molecular weight:
63 kDa
Reactions
2 pyruvate = 2-acetolactate + CO(2).
General function:
Involved in acetolactate synthase activity
Specific function:
2 pyruvate = 2-acetolactate + CO(2)
Gene Name:
ilvH
Locus Tag:
PA4695
Molecular weight:
17.8 kDa
Reactions
2 pyruvate = 2-acetolactate + CO(2).
General function:
Involved in biosynthetic process
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
trpE
Locus Tag:
PA0609
Molecular weight:
54.6 kDa
Reactions
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate.
General function:
Involved in anthranilate phosphoribosyltransferase activity
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
trpD
Locus Tag:
PA0650
Molecular weight:
37.4 kDa
Reactions
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate.
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in D-serine ammonia-lyase activity
Specific function:
D-serine = pyruvate + NH(3)
Gene Name:
dsdA
Locus Tag:
PA3357
Molecular weight:
48.2 kDa
Reactions
D-serine = pyruvate + NH(3).
General function:
Involved in catalytic activity
Specific function:
Catalyzes the formation of alpha-ketobutyrate from threonine in a two-step reaction. The first step is a dehydration of threonine, followed by rehydration and liberation of ammonia. Deaminates L-threonine, but also L-serine to a lesser extent
Gene Name:
ilvA
Locus Tag:
PA1326
Molecular weight:
55.9 kDa
Reactions
L-threonine = 2-oxobutanoate + NH(3).
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2). It contains multiple copies of three enzymatic components:pyruvate dehydrogenase (E1), dihydrolipoamide acetyltransferase (E2) and lipoamide dehydrogenase (E3)
Gene Name:
aceF
Locus Tag:
PA5016
Molecular weight:
56.7 kDa
Reactions
Acetyl-CoA + enzyme N(6)-(dihydrolipoyl)lysine = CoA + enzyme N(6)-(S-acetyldihydrolipoyl)lysine.
General function:
Involved in magnesium ion binding
Specific function:
Pyruvate + ferricytochrome b1 + H(2)O = acetate + CO(2) + ferrocytochrome b1
Gene Name:
poxB
Locus Tag:
PA5297
Molecular weight:
62.3 kDa
Reactions
Pyruvate + ubiquinone + H(2)O = acetate + CO(2) + ubiquinol.
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in N-acetylglucosamine transport
Gene Name:
nagE
Locus Tag:
PA3761
Molecular weight:
60.6 kDa
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in D-amino-acid dehydrogenase activity
Specific function:
Oxidative deamination of D-amino acids
Gene Name:
dadA
Locus Tag:
PA5304
Molecular weight:
47.1 kDa
Reactions
A D-amino acid + H(2)O + acceptor = a 2-oxo acid + NH(3) + reduced acceptor.
General function:
Involved in catalytic activity
Specific function:
L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O
Gene Name:
dapA
Locus Tag:
PA1010
Molecular weight:
31.4 kDa
Reactions
L-aspartate 4-semialdehyde + pyruvate = dihydrodipicolinate + 2 H(2)O.
General function:
Involved in catalytic activity
Specific function:
Interconversion of serine and glycine
Gene Name:
glyA
Locus Tag:
PA4602
Molecular weight:
45.2 kDa
Reactions
5,10-methylenetetrahydrofolate + glycine + H(2)O = tetrahydrofolate + L-serine.
General function:
Involved in magnesium ion binding
Specific function:
ATP + pyruvate = ADP + phosphoenolpyruvate
Gene Name:
pykF
Locus Tag:
PA1498
Molecular weight:
51.5 kDa
Reactions
ATP + pyruvate = ADP + phosphoenolpyruvate.
General function:
Involved in oxidoreductase activity
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2). It contains multiple copies of three enzymatic components:pyruvate dehydrogenase (E1), dihydrolipoamide acetyltransferase (E2) and lipoamide dehydrogenase (E3)
Gene Name:
aceE
Locus Tag:
PA5015
Molecular weight:
99.6 kDa
Reactions
Pyruvate + [dihydrolipoyllysine-residue acetyltransferase] lipoyllysine = [dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + CO(2).
General function:
Involved in L-serine ammonia-lyase activity
Specific function:
Deaminates also threonine, particularly when it is present in high concentration
Gene Name:
sdaA
Locus Tag:
PA2443
Molecular weight:
48.9 kDa
Reactions
L-serine = pyruvate + NH(3).
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in fructose transport
Gene Name:
fruA
Locus Tag:
PA3560
Molecular weight:
59 kDa
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in magnesium ion binding
Specific function:
ATP + pyruvate = ADP + phosphoenolpyruvate
Gene Name:
pykA
Locus Tag:
PA4329
Molecular weight:
52.3 kDa
Reactions
ATP + pyruvate = ADP + phosphoenolpyruvate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the phosphorylation of pyruvate to phosphoenolpyruvate
Gene Name:
ppsA
Locus Tag:
PA1770
Molecular weight:
85.8 kDa
Reactions
ATP + pyruvate + H(2)O = AMP + phosphoenolpyruvate + phosphate.
General function:
Involved in oxidoreductase activity
Specific function:
(S)-malate + NAD(+) = pyruvate + CO(2) + NADH
Gene Name:
sfcA
Locus Tag:
PA3471
Molecular weight:
62.4 kDa
Reactions
(S)-malate + NAD(+) = pyruvate + CO(2) + NADH.
General function:
Involved in 4-amino-4-deoxychorismate lyase activity
Specific function:
Converts 4-amino-4-deoxychorismate into 4-aminobenzoate (PABA) and pyruvate
Gene Name:
pabC
Locus Tag:
PA2964
Molecular weight:
29.9 kDa
Reactions
4-amino-4-deoxychorismate = 4-aminobenzoate + pyruvate.
General function:
Involved in L-serine ammonia-lyase activity
Specific function:
Deaminates also threonine, particularly when it is present in high concentration
Gene Name:
sdaB
Locus Tag:
PA5379
Molecular weight:
49.2 kDa
Reactions
L-serine = pyruvate + NH(3).
General function:
Involved in catalytic activity
Specific function:
(S)-lactate + 2 ferricytochrome c = pyruvate + 2 ferrocytochrome c + 2 H(+)
Gene Name:
lldD
Locus Tag:
PA4771
Molecular weight:
41.1 kDa
Reactions
(S)-lactate + 2 ferricytochrome c = pyruvate + 2 ferrocytochrome c + 2 H(+).
General function:
Involved in protein binding
Specific function:
Component of the phosphoenolpyruvate-dependent nitrogen- metabolic phosphotransferase system (nitrogen-metabolic PTS), that seems to be involved in regulating nitrogen metabolism. Enzyme I- Ntr transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (NPr). Could function in the transcriptional regulation of sigma-54 dependent operons in conjunction with the NPr (ptsO) and EIIA-Ntr (ptsN) proteins
Gene Name:
ptsP
Locus Tag:
PA0337
Molecular weight:
83.6 kDa
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatB
Locus Tag:
PA4484
Molecular weight:
53.1 kDa
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Fermentative lactate dehydrogenase
Gene Name:
ldhA
Locus Tag:
PA0927
Molecular weight:
35.8 kDa
Reactions
(R)-lactate + NAD(+) = pyruvate + NADH.
General function:
Involved in transporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatA
Locus Tag:
PA4483
Molecular weight:
51.9 kDa
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
General function:
Involved in lyase activity
Specific function:
Catalyzes the cleavage of L-allo-threonine and L- threonine to glycine and acetaldehyde. L-threo-phenylserine and L- erythro-phenylserine are also good substrates
Gene Name:
ltaE
Locus Tag:
PA0902
Molecular weight:
35.4 kDa
Reactions
L-threonine = glycine + acetaldehyde.
L-allo-threonine = glycine + acetaldehyde.
General function:
Involved in carbon-carbon lyase activity
Specific function:
Catalyzes the reversible retro-aldol cleavage of 2-keto- 3-deoxy-L-rhamnonate (KDR) to pyruvate and lactaldehyde. 2-keto-3- deoxy-L-mannonate, 2-keto-3-deoxy-L-lyxonate and 4-hydroxy-2- ketoheptane-1,7-dioate (HKHD) are also reasonably good substrates, although 2-keto-3-deoxy-L-rhamnonate is likely to be the physiological substrate
Gene Name:
rhmA
Locus Tag:
PA4128
Molecular weight:
28.2 kDa
Reactions
2-dehydro-3-deoxy-L-rhamnonate = pyruvate + (R)-lactaldehyde.
General function:
Involved in oxidoreductase activity
Specific function:
(S)-malate + NADP(+) = pyruvate + CO(2) + NADPH
Gene Name:
maeB
Locus Tag:
PA5046
Molecular weight:
45.4 kDa
Reactions
(S)-malate + NADP(+) = pyruvate + CO(2) + NADPH.
General function:
Involved in 1-deoxy-D-xylulose-5-phosphate synthase activity
Specific function:
Catalyzes the acyloin condensation reaction between C atoms 2 and 3 of pyruvate and glyceraldehyde 3-phosphate to yield 1-deoxy-D-xylulose-5-phosphate (DXP)
Gene Name:
dxs
Locus Tag:
PA4044
Molecular weight:
68 kDa
Reactions
Pyruvate + D-glyceraldehyde 3-phosphate = 1-deoxy-D-xylulose 5-phosphate + CO(2).
General function:
Involved in catalytic activity
Specific function:
Catalyzes the formation of pyruvate and succinate from 2-methylisocitrate
Gene Name:
prpB
Locus Tag:
PA0796
Molecular weight:
32.1 kDa
Reactions
(2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate = pyruvate + succinate.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatC
Locus Tag:
PA4482
Molecular weight:
10.5 kDa
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Specific function unknown
Gene Name:
yfbQ
Locus Tag:
PA2828
Molecular weight:
44.8 kDa
Reactions
L-alanine + 2-oxoglutarate = pyruvate + L-glutamate.
General function:
Amino acid transport and metabolism
Specific function:
Specific function unknown
Gene Name:
yfdZ
Locus Tag:
PA4715
Molecular weight:
46.1 kDa
Reactions
L-alanine + 2-oxoglutarate = pyruvate + L-glutamate.

Transporters

General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in N-acetylglucosamine transport
Gene Name:
nagE
Locus Tag:
PA3761
Molecular weight:
60.6 kDa
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in fructose transport
Gene Name:
fruA
Locus Tag:
PA3560
Molecular weight:
59 kDa
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatC
Locus Tag:
PA4482
Molecular weight:
10.5 kDa