You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00170
NamePyruvaldehyde
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionMethylglyoxal, also called pyruvaldehyde or 2-oxopropanal is the aldehyde form of pyruvic acid. It has two carbonyl groups, so it is a dicarbonyl compound. Methylglyoxal is both an aldehyde and a ketone. Methylglyoxal is formed as a side-product of several metabolic pathways. It may form from 3-amino acetone, which is an intermediate of threonine catabolism, as well as through lipid peroxidation. However, the most important source is glycolysis. Here, methylglyoxal arises from nonenzymatic phosphate elimination from glyceraldehyde phosphate and dihydroxyacetone phosphate, two intermediates of glycolysis. Methylglyoxal is toxic due to its high reactivity. [Wikipedia]
Structure
Thumb
Synonyms
  • 1-Ketopropionaldehyde
  • 1,2-Propanedione
  • 2-keto Propionaldehyde
  • 2-Ketopropionaldehyde
  • 2-oxo-Propionaldehyde
  • 2-Oxopropanal
  • Acetylformaldehyde
  • Acetylformyl
  • alpha-Ketopropionaldehyde
  • Ketopropionaldehyde
  • Methylglyoxal
  • Propanedione
  • Propanolone
  • Pyroracemic aldehyde
  • Pyruvaldehyde
  • Pyruvic aldehyde
  • 2-Oxopropionaldehyde
  • CH3COCHO
  • a-Ketopropionaldehyde
  • Α-ketopropionaldehyde
  • Aldehyde, pyruvic
  • Oxopropanal
CAS number78-98-8
WeightAverage: 72.0627
Monoisotopic: 72.021129372
InChI KeyAIJULSRZWUXGPQ-UHFFFAOYSA-N
InChIInChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3
IUPAC Name2-oxopropanal
Traditional IUPAC Namemethylglyoxal
Chemical FormulaC3H4O2
SMILES[H]C(=O)C(=O)C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha ketoaldehydes
Alternative Parents
Substituents
  • Alpha-ketoaldehyde
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point< 25 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility180 g/LALOGPS
logP-0.38ALOGPS
logP0.2ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)16.38ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity17.05 m³·mol⁻¹ChemAxon
Polarizability6.42 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
AcidicFDB008295
BrownFDB008295
EtherealFDB008295
RumFDB008295
SweetFDB008295
SMPDB Pathways
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycine, serine and threonine metabolismec00260 Map00260
Pyruvate metabolismec00620 Map00620
SMPDB Reactions
Lactaldehyde + NADPPyruvaldehyde + NADP + hydron
Glutathione + PyruvaldehydeS-Lactoylglutathione
KEGG Reactions
Aminoacetone + water + oxygenPyruvaldehyde + Hydrogen peroxide + Ammonium
Pyruvaldehyde + NADPH + hydronNADP + Lactaldehyde
Pyruvaldehyde + GlutathioneS-Lactoylglutathione
Dihydroxyacetone phosphatePyruvaldehyde + phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Chen, C. N., Porubleva, L., Shearer, G., Svrakic, M., Holden, L. G., Dover, J. L., Johnston, M., Chitnis, P. R., Kohl, D. H. (2003). "Associating protein activities with their genes: rapid identification of a gene encoding a methylglyoxal reductase in the yeast Saccharomyces cerevisiae." Yeast 20:545-554.12722185
  • Inoue, Y., Watanabe, K., Shimosaka, M., Saikusa, T., Fukuda, Y., Murata, K., Kimura, A. (1985). "Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae." Eur J Biochem 153:243-247.3908097
Synthesis Reference:Zhang, Jing-An; Chen, Yu-Ping. Synthesis of pyruvaldehyde. Jingxi Huagong (2000), 17(9), 507-510.
External Links:
ResourceLink
CHEBI ID17158
HMDB IDHMDB01167
Pubchem Compound ID880
Kegg IDC00546
ChemSpider ID857
FOODB IDFDB008295
WikipediaMethylglyoxal
BioCyc IDMETHYL-GLYOXAL

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the irreversible reduction of the cytotoxic compound methylglyoxal (MG) to (R)-lactaldehyde as an alternative to detoxification of MG by glyoxalase I GLO1. MG is synthesized via a bypath of glycolysis from dihydroxyacetone phosphate and is believed to play a role in cell cycle regulation and stress adaptation
Gene Name:
GRE2
Uniprot ID:
Q12068
Molecular weight:
38169.19922
Reactions
Lactaldehyde + NADP(+) → methylglyoxal + NADPH.
3-methylbutanol + NAD(P)+ → 3-methylbutanal + NAD(P)H + H+
General function:
Involved in oxidoreductase activity
Specific function:
Reduces the cytotoxic compound methylglyoxal (MG) to (R)-lactaldehyde similar to GRE2. MG is synthesized via a bypath of glycolysis from dihydroxyacetone phosphate and is believed to play a role in cell cycle regulation and stress adaptation. In pentose-fermenting yeasts, aldose reductase catalyzes the reduction of xylose into xylitol. The purified enzyme catalyzes this reaction, but the inability of S.cerevisiae to grow on xylose as sole carbon source indicates that the physiological function is more likely methylglyoxal reduction
Gene Name:
GRE3
Uniprot ID:
P38715
Molecular weight:
37118.5
Reactions
Alditol + NAD(P)(+) → aldose + NAD(P)H.
(R)-lactaldehyde + NADP(+) → methylglyoxal + NADPH.
General function:
Involved in lactoylglutathione lyase activity
Specific function:
Catalyzes the conversion of hemimercaptal, formed from methylglyoxal and glutathione, to S-lactoylglutathione
Gene Name:
GLO1
Uniprot ID:
P50107
Molecular weight:
37208.69922
Reactions
(R)-S-lactoylglutathione → glutathione + methylglyoxal.