Pyruvaldehyde (YMDB00170)

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Identification

YMDB ID

YMDB00170

Name

Pyruvaldehyde

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Methylglyoxal, 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 number

78-98-8

Weight

Average: 72.0627
Monoisotopic: 72.021129372

InChI Key

AIJULSRZWUXGPQ-UHFFFAOYSA-N

InChI

InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3

IUPAC Name

2-oxopropanal

Traditional IUPAC Name

methylglyoxal

Chemical Formula

C₃H₄O₂

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha ketoaldehydes

Alternative Parents

Substituents

Alpha-ketoaldehyde
Ketone
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

propanals (CHEBI:17158 )
2-oxo aldehyde (CHEBI:17158 )
a ketoaldehyde (METHYL-GLYOXAL )

Physical Properties

State

Liquid

Charge

Melting point

< 25 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	180 g/L	ALOGPS
logP	-0.38	ALOGPS
logP	0.2	ChemAxon
logS	0.4	ALOGPS
pKa (Strongest Acidic)	16.38	ChemAxon
pKa (Strongest Basic)	-8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	17.05 m³·mol⁻¹	ChemAxon
Polarizability	6.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Acidic	FDB031000
Brown	FDB031000
Ethereal	FDB031000
Rum	FDB031000
Sweet	FDB031000

SMPDB Pathways

Pyruvate metabolism

PW002447

KEGG Pathways

Glycine, serine and threonine metabolism	ec00260
Pyruvate metabolism	ec00620

SMPDB Reactions

Lactaldehyde + NADP ↔ Pyruvaldehyde + NADP + hydron

Glutathione + Pyruvaldehyde ↔ S-Lactoylglutathione

KEGG Reactions

Aminoacetone + water + oxygen → Pyruvaldehyde + Hydrogen peroxide + Ammonium

Pyruvaldehyde + NADPH + hydron → NADP + Lactaldehyde

Pyruvaldehyde + Glutathione → S-Lactoylglutathione

Dihydroxyacetone phosphate → Pyruvaldehyde + phosphate

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-43f9b3c94058c64733b5	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00dj-9000000000-964129275940a60a617d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-006y-9000000000-0ae1e5fd2d50b28f967c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00dj-9000000000-964129275940a60a617d	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-110d6fcd891f2c54a2cb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-9000000000-bec3651f9ea6825cf4f7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-8db5b1ba128748e220c3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-f968a2358e6fd85ae268	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-0797bdeaa575b54943c5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uk9-9000000000-89ef1c082b2ef672eb67	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-5b936b9153956c2f64be	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-9190b139940adf0d92c6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-570ca33f905cecb028a1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-482389dce4f05675f174	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-79267be0bc618dc8018f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-87bbaed151efac084591	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	17158
HMDB ID	HMDB01167
Pubchem Compound ID	880
Kegg ID	C00546
ChemSpider ID	857
FOODB ID	FDB031000
Wikipedia	Methylglyoxal
BioCyc ID	METHYL-GLYOXAL

Enzymes

Protein Details

1. NADPH-dependent methylglyoxal reductase GRE2

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+

Protein Details

2. NADPH-dependent aldose reductase GRE3

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.

Protein Details

3. Lactoylglutathione lyase

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.

Structure for #<Compound:0xaa512c28>

Enzymes

Reactions

Reactions

Reactions