Human Metabolome Database: Showing metabocard for Pyruvaldehyde (HMDB0001167)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11) Show 11 proteins XML

enzymes (11) Show 11 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2018-03-12 21:55:20 UTC

HMDB ID

HMDB0001167

Secondary Accession Numbers

HMDB01167

Metabolite Identification

Common Name

Pyruvaldehyde

Description

Pyruvaldehyde is an organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.

Structure

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

Synonyms

Value	Source
1,2-Propanedione	ChEBI
2-Ketopropionaldehyde	ChEBI
2-Oxopropanal	ChEBI
2-Oxopropionaldehyde	ChEBI
Acetylformaldehyde	ChEBI
Acetylformyl	ChEBI
alpha-Ketopropionaldehyde	ChEBI
CH3COCHO	ChEBI
Pyruvic aldehyde	ChEBI
a-Ketopropionaldehyde	Generator
α-ketopropionaldehyde	Generator
1-Ketopropionaldehyde	HMDB
2-keto Propionaldehyde	HMDB
2-oxo-Propionaldehyde	HMDB
Ketopropionaldehyde	HMDB
Methylglyoxal	HMDB
Propanedione	HMDB
Propanolone	HMDB
Pyroracemic aldehyde	HMDB
Aldehyde, pyruvic	MeSH
Oxopropanal	MeSH

Chemical Formula

C₃H₄O₂

Average Molecular Weight

72.0627

Monoisotopic Molecular Weight

72.021129372

IUPAC Name

2-oxopropanal

Traditional Name

methylglyoxal

CAS Registry Number

78-98-8

SMILES

CC(=O)C=O

InChI Identifier

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

InChI Key

AIJULSRZWUXGPQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound 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 )

Ontology

Physiological effect

Health effect:

Health condition:

Diabetes mellitus type 2

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Biofluid and excreta:

Cell and elements:

Extracellular

Cell:

Fibroblast

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

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

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-43f9b3c94058c64733b5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00dj-9000000000-964129275940a60a617d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-006y-9000000000-0ae1e5fd2d50b28f967c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00dj-9000000000-964129275940a60a617d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-110d6fcd891f2c54a2cb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-9000000000-bec3651f9ea6825cf4f7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-8db5b1ba128748e220c3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-f968a2358e6fd85ae268	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-0797bdeaa575b54943c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uk9-9000000000-89ef1c082b2ef672eb67	View in MoNA

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Location

Fibroblasts
Kidney
Lens
Liver

Pathways

Name	SMPDB/Pathwhiz	KEGG
3-Phosphoglycerate dehydrogenase deficiency		Not Available
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)		Not Available
Dimethylglycine Dehydrogenase Deficiency		Not Available
Dimethylglycine Dehydrogenase Deficiency		Not Available
Glycine and Serine Metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	110.0 +/- 77.0 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.59 (0.44-0.74) uM	Adult (>18 years old)	Both	Normal	18760976	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.0 (2.4-3.6) uM	Adult (>18 years old)	Both	Diabetes	18760976	details
Urine	Detected and Quantified	0.22 (0.16-0.23) umol/mmol creatinine	Adult (>18 years old)	Both	Diabetes	18760976	details

Associated Disorders and Diseases

Disease References

Diabetes mellitus type 2
Khuhawar MY, Zardari LA, Laghari AJ: Capillary gas chromatographic determination of methylglyoxal from serum of diabetic patients by precolumn derivatization with 1,2-diamonopropane. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Sep 15;873(1):15-9. doi: 10.1016/j.jchromb.2008.04.048. Epub 2008 May 17. [PubMed:18760976 ]

Associated OMIM IDs

125853 (Diabetes mellitus type 2)

External Links

DrugBank ID

DB03587

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17158

References

Synthesis Reference

Zhang, Jing-An; Chen, Yu-Ping. Synthesis of pyruvaldehyde. Jingxi Huagong (2000), 17(9), 507-510.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Wondrak GT, Cervantes-Laurean D, Roberts MJ, Qasem JG, Kim M, Jacobson EL, Jacobson MK: Identification of alpha-dicarbonyl scavengers for cellular protection against carbonyl stress. Biochem Pharmacol. 2002 Feb 1;63(3):361-73. [PubMed:11853687 ]
Mottaran E, Stewart SF, Rolla R, Vay D, Cipriani V, Moretti M, Vidali M, Sartori M, Rigamonti C, Day CP, Albano E: Lipid peroxidation contributes to immune reactions associated with alcoholic liver disease. Free Radic Biol Med. 2002 Jan 1;32(1):38-45. [PubMed:11755315 ]
Lo TW, Selwood T, Thornalley PJ: The reaction of methylglyoxal with aminoguanidine under physiological conditions and prevention of methylglyoxal binding to plasma proteins. Biochem Pharmacol. 1994 Nov 16;48(10):1865-70. [PubMed:7986197 ]
Gildersleeve DL, Tobes MC, Natale RB: Rapid analysis for methylglyoxal bis(guanylhydrazone) by reversed-phase ion-pair liquid chromatography. Clin Chem. 1985 Dec;31(12):1979-84. [PubMed:4064286 ]
Ahmed N, Thornalley PJ, Dawczynski J, Franke S, Strobel J, Stein G, Haik GM: Methylglyoxal-derived hydroimidazolone advanced glycation end-products of human lens proteins. Invest Ophthalmol Vis Sci. 2003 Dec;44(12):5287-92. [PubMed:14638728 ]
Seppanen P, Alhonen-Hongisto L, Janne J: Polyamine deprivation-induced enhanced uptake of methylglyoxal bis(guanylhydrazone) by tumor cells. Biochim Biophys Acta. 1981 May 5;674(2):169-77. [PubMed:6786360 ]
Ahmed MU, Brinkmann Frye E, Degenhardt TP, Thorpe SR, Baynes JW: N-epsilon-(carboxyethyl)lysine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins. Biochem J. 1997 Jun 1;324 ( Pt 2):565-70. [PubMed:9182719 ]
Riley ML, Harding JJ: The reaction of methylglyoxal with human and bovine lens proteins. Biochim Biophys Acta. 1995 Jan 25;1270(1):36-43. [PubMed:7827133 ]
Beisswenger PJ, Drummond KS, Nelson RG, Howell SK, Szwergold BS, Mauer M: Susceptibility to diabetic nephropathy is related to dicarbonyl and oxidative stress. Diabetes. 2005 Nov;54(11):3274-81. [PubMed:16249455 ]
Nemet I, Varga-Defterdarovic L, Turk Z: Preparation and quantification of methylglyoxal in human plasma using reverse-phase high-performance liquid chromatography. Clin Biochem. 2004 Oct;37(10):875-81. [PubMed:15369718 ]
Thornalley PJ, Argirova M, Ahmed N, Mann VM, Argirov O, Dawnay A: Mass spectrometric monitoring of albumin in uremia. Kidney Int. 2000 Nov;58(5):2228-34. [PubMed:11044246 ]
Baskaran S, Rajan DP, Balasubramanian KA: Formation of methylglyoxal by bacteria isolated from human faeces. J Med Microbiol. 1989 Mar;28(3):211-5. [PubMed:2926792 ]
Kuhla B, Luth HJ, Haferburg D, Boeck K, Arendt T, Munch G: Methylglyoxal, glyoxal, and their detoxification in Alzheimer's disease. Ann N Y Acad Sci. 2005 Jun;1043:211-6. [PubMed:16037241 ]
Schupp N, Schinzel R, Heidland A, Stopper H: Genotoxicity of advanced glycation end products: involvement of oxidative stress and of angiotensin II type 1 receptors. Ann N Y Acad Sci. 2005 Jun;1043:685-95. [PubMed:16037294 ]
Haik GM Jr, Lo TW, Thornalley PJ: Methylglyoxal concentration and glyoxalase activities in the human lens. Exp Eye Res. 1994 Oct;59(4):497-500. [PubMed:7859825 ]
Shamsi FA, Lin K, Sady C, Nagaraj RH: Methylglyoxal-derived modifications in lens aging and cataract formation. Invest Ophthalmol Vis Sci. 1998 Nov;39(12):2355-64. [PubMed:9804144 ]
Jan CR, Chen CH, Wang SC, Kuo SY: Effect of methylglyoxal on intracellular calcium levels and viability in renal tubular cells. Cell Signal. 2005 Jul;17(7):847-55. Epub 2004 Dec 8. [PubMed:15763427 ]
Ahmed N, Dobler D, Dean M, Thornalley PJ: Peptide mapping identifies hotspot site of modification in human serum albumin by methylglyoxal involved in ligand binding and esterase activity. J Biol Chem. 2005 Feb 18;280(7):5724-32. Epub 2004 Nov 22. [PubMed:15557329 ]

Only showing the first 10 proteins. There are 11 proteins in total.

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Enzymes

Enzyme Details

1. Aldose reductase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:: AKR1B1
Uniprot ID:: P15121
Molecular weight:: 35853.125

Reactions

Lactaldehyde + NAD → Pyruvaldehyde + NADH + Hydrogen Ion	details

Enzyme Details

2. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Reactions

Aminoacetone + Water + Oxygen → Pyruvaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

3. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Reactions

Aminoacetone + Water + Oxygen → Pyruvaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

4. Bile salt-activated lipase

General function:: Lipid transport and metabolism
Specific function:: Catalyzes fat and vitamin absorption. Acts in concert with pancreatic lipase and colipase for the complete digestion of dietary triglycerides.
Gene Name:: CEL
Uniprot ID:: P19835
Molecular weight:: 79666.385

Enzyme Details

5. Amiloride-sensitive amine oxidase [copper-containing]

General function:: Involved in copper ion binding
Specific function:: Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:: ABP1
Uniprot ID:: P19801
Molecular weight:: 85377.1

Enzyme Details

6. Glyoxylate reductase/hydroxypyruvate reductase

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Enzyme with hydroxy-pyruvate reductase, glyoxylate reductase and D-glycerate dehydrogenase enzymatic activities. Reduces hydroxypyruvate to D-glycerate, glyoxylate to glycolate oxidizes D-glycerate to hydroxypyruvate.
Gene Name:: GRHPR
Uniprot ID:: Q9UBQ7
Molecular weight:: 35667.875

Reactions

D-Lactaldehyde + NAD → Pyruvaldehyde + NADH + Hydrogen Ion	details

Enzyme Details

7. Lactoylglutathione lyase

General function:: Involved in lactoylglutathione lyase activity
Specific function:: Catalyzes the conversion of hemimercaptal, formed from methylglyoxal and glutathione, to S-lactoylglutathione. Involved in the regulation of TNF-induced transcriptional activity of NF-kappa-B.
Gene Name:: GLO1
Uniprot ID:: Q04760
Molecular weight:: 20777.515

Reactions

S-Lactoylglutathione → Glutathione + Pyruvaldehyde	details

Enzyme Details

8. Membrane primary amine oxidase

General function:: Involved in copper ion binding
Specific function:: Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:: AOC3
Uniprot ID:: Q16853
Molecular weight:: 84621.27

Reactions

Aminoacetone + Water + Oxygen → Pyruvaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

9. Retina-specific copper amine oxidase

General function:: Involved in copper ion binding
Specific function:: Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:: AOC2
Uniprot ID:: O75106
Molecular weight:: 80515.11

Reactions

Aminoacetone + Water + Oxygen → Pyruvaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

10. Retinol dehydrogenase 13

General function:: Involved in oxidoreductase activity
Specific function:: Does not exhibit retinol dehydrogenase (RDH) activity in vitro
Gene Name:: RDH13
Uniprot ID:: Q8NBN7
Molecular weight:: 35931.8

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Pyruvaldehyde (HMDB0001167)

Structure for HMDB0001167 (Pyruvaldehyde)

Enzymes

Reactions

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