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Showing metabocard for Pyruvaldehyde (HMDB0001167)

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enzymes (11) Show 11 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:29 UTC
HMDB IDHMDB0001167
Secondary Accession Numbers
  • HMDB01167
Metabolite Identification
Common NamePyruvaldehyde
DescriptionPyruvaldehyde, also known as 2-oxopropanal or 1,2-propanedione, 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. Pyruvaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Pyruvaldehyde exists in all living species, ranging from bacteria to humans. In humans, pyruvaldehyde is involved in spermidine and spermine biosynthesis. Outside of the human body, Pyruvaldehyde has been detected, but not quantified in, several different foods, such as prairie turnips, chervils, japanese walnuts, corns, and calabash. This could make pyruvaldehyde a potential biomarker for the consumption of these foods.
Structure
Data?1676999729
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001167 (Pyruvaldehyde)


  Mrv1652305112022002D          

  5  4  0  0  0  0            999 V2000
   -2.0199    1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7343    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0199    2.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3054    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5909    1.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  4  1  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
M  END
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3D MOL for HMDB0001167 (Pyruvaldehyde)

HMDB0001167
     RDKit          3D
Pyruvaldehyde
  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.1067   -0.2215   -0.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251    0.5803   -0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0522    1.8271   -0.1800 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -0.0634    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4712   -1.3196    0.1734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7263    0.0794    0.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9017   -1.3048    0.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944   -0.0599   -0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3580    0.4824    0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  4  9  1  0
M  END
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3D SDF for HMDB0001167 (Pyruvaldehyde)


  Mrv1652305112022002D          

  5  4  0  0  0  0            999 V2000
   -2.0199    1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7343    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0199    2.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3054    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5909    1.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  4  1  0  0  0  0
  1  3  2  0  0  0  0
  4  5  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001167

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)C=O

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

> <INCHI_KEY>
AIJULSRZWUXGPQ-UHFFFAOYSA-N

> <FORMULA>
C3H4O2

> <MOLECULAR_WEIGHT>
72.0627

> <EXACT_MASS>
72.021129372

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
6.421644584802687

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxopropanal

> <ALOGPS_LOGP>
-0.38

> <JCHEM_LOGP>
0.19595048433333334

> <ALOGPS_LOGS>
0.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.38193786809808

> <JCHEM_PKA_STRONGEST_BASIC>
-8.021418549550578

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
17.0511

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylglyoxal

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0001167 (Pyruvaldehyde)

HMDB0001167
     RDKit          3D
Pyruvaldehyde
  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.1067   -0.2215   -0.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251    0.5803   -0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0522    1.8271   -0.1800 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226   -0.0634    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4712   -1.3196    0.1734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7263    0.0794    0.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9017   -1.3048    0.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944   -0.0599   -0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3580    0.4824    0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  4  9  1  0
M  END
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PDB for HMDB0001167 (Pyruvaldehyde)

HEADER    PROTEIN                                 11-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-MAY-20         0                                  
HETATM    1  C   UNK     0      -3.770   2.666   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.104   1.896   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.770   4.206   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.437   1.896   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.103   2.666   0.000  0.00  0.00           O+0
CONECT    1    2    4    3                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0001167 (Pyruvaldehyde)

COMPND    HMDB0001167
HETATM    1  C1  UNL     1      -1.107  -0.221  -0.015  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.125   0.580  -0.055  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.052   1.827  -0.180  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.423  -0.063   0.048  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.471  -1.320   0.173  1.00  0.00           O  
HETATM    6  H1  UNL     1      -1.726   0.079   0.855  1.00  0.00           H  
HETATM    7  H2  UNL     1      -0.902  -1.305   0.104  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.694  -0.060  -0.955  1.00  0.00           H  
HETATM    9  H4  UNL     1       2.358   0.482   0.024  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    3    4
CONECT    4    5    5    9
END
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SMILES for HMDB0001167 (Pyruvaldehyde)

CC(=O)C=O
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INCHI for HMDB0001167 (Pyruvaldehyde)

InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,2-PropanedioneChEBI
2-KetopropionaldehydeChEBI
2-OxopropanalChEBI
2-OxopropionaldehydeChEBI
AcetylformaldehydeChEBI
AcetylformylChEBI
alpha-KetopropionaldehydeChEBI
CH3COCHOChEBI
Pyruvic aldehydeChEBI
a-KetopropionaldehydeGenerator
Α-ketopropionaldehydeGenerator
1-KetopropionaldehydeHMDB
2-Keto propionaldehydeHMDB
2-oxo-PropionaldehydeHMDB
KetopropionaldehydeHMDB
MethylglyoxalHMDB
PropanedioneHMDB
PropanoloneHMDB
Pyroracemic aldehydeHMDB
Aldehyde, pyruvicHMDB
OxopropanalHMDB
Chemical FormulaC3H4O2
Average Molecular Weight72.0627
Monoisotopic Molecular Weight72.021129372
IUPAC Name2-oxopropanal
Traditional Namemethylglyoxal
CAS Registry Number78-98-8
SMILES
CC(=O)C=O
InChI Identifier
InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3
InChI KeyAIJULSRZWUXGPQ-UHFFFAOYSA-N
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
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+111.51231661259
DarkChem[M-H]-104.43131661259
AllCCS[M+H]+121.13132859911
AllCCS[M-H]-128.8832859911
DeepCCS[M+H]+119.84430932474
DeepCCS[M-H]-117.89830932474
DeepCCS[M-2H]-153.56430932474
DeepCCS[M+Na]+128.01530932474
AllCCS[M+H]+121.132859911
AllCCS[M+H-H2O]+116.632859911
AllCCS[M+NH4]+125.432859911
AllCCS[M+Na]+126.632859911
AllCCS[M-H]-128.932859911
AllCCS[M+Na-2H]-134.432859911
AllCCS[M+HCOO]-140.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PyruvaldehydeCC(=O)C=O905.5Standard polar33892256
PyruvaldehydeCC(=O)C=O484.1Standard non polar33892256
PyruvaldehydeCC(=O)C=O535.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyruvaldehyde,1TMS,isomer #1C=C(C=O)O[Si](C)(C)C841.3Semi standard non polar33892256
Pyruvaldehyde,1TMS,isomer #1C=C(C=O)O[Si](C)(C)C785.1Standard non polar33892256
Pyruvaldehyde,1TMS,isomer #1C=C(C=O)O[Si](C)(C)C1045.0Standard polar33892256
Pyruvaldehyde,1TBDMS,isomer #1C=C(C=O)O[Si](C)(C)C(C)(C)C1100.9Semi standard non polar33892256
Pyruvaldehyde,1TBDMS,isomer #1C=C(C=O)O[Si](C)(C)C(C)(C)C1012.4Standard non polar33892256
Pyruvaldehyde,1TBDMS,isomer #1C=C(C=O)O[Si](C)(C)C(C)(C)C1235.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pyruvaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-43f9b3c94058c64733b52016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyruvaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyruvaldehyde Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00dj-9000000000-964129275940a60a617d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyruvaldehyde Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-006y-9000000000-0ae1e5fd2d50b28f967c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyruvaldehyde Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00dj-9000000000-964129275940a60a617d2012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 10V, Positive-QTOFsplash10-00di-9000000000-110d6fcd891f2c54a2cb2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 20V, Positive-QTOFsplash10-05fr-9000000000-bec3651f9ea6825cf4f72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 40V, Positive-QTOFsplash10-0a4i-9000000000-8db5b1ba128748e220c32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 10V, Negative-QTOFsplash10-00di-9000000000-f968a2358e6fd85ae2682015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 20V, Negative-QTOFsplash10-00di-9000000000-0797bdeaa575b54943c52015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 40V, Negative-QTOFsplash10-0uk9-9000000000-89ef1c082b2ef672eb672015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 10V, Negative-QTOFsplash10-00di-9000000000-5b936b9153956c2f64be2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 20V, Negative-QTOFsplash10-00di-9000000000-9190b139940adf0d92c62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 40V, Negative-QTOFsplash10-0006-9000000000-570ca33f905cecb028a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 10V, Positive-QTOFsplash10-0006-9000000000-482389dce4f05675f1742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 20V, Positive-QTOFsplash10-0006-9000000000-79267be0bc618dc8018f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyruvaldehyde 40V, Positive-QTOFsplash10-0006-9000000000-87bbaed151efac0845912021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Eye Lens
  • Fibroblasts
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified110.0 +/- 77.0 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified0.653 +/- 0.167 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified0.59 (0.44-0.74) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.528 +/- 0.250 uMAdult (>18 years old)Both
Uremia		 details
BloodDetected and Quantified3.0 (2.4-3.6) uMAdult (>18 years old)BothDiabetes details
UrineDetected and Quantified0.22 (0.16-0.23) umol/mmol creatinineAdult (>18 years old)BothDiabetes details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. 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 ]
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Associated OMIM IDs
DrugBank IDDB03587
Phenol Explorer Compound IDNot Available
FooDB IDFDB031000
KNApSAcK IDC00007562
Chemspider ID857
KEGG Compound IDC00546
BioCyc IDMETHYL-GLYOXAL
BiGG ID35307
Wikipedia LinkMethylglyoxal
METLIN ID6049
PubChem Compound880
PDB IDNot Available
ChEBI ID17158
Food Biomarker OntologyNot Available
VMH IDMTHGXL
MarkerDB IDMDB00029995
Good Scents IDNot Available
References
Synthesis ReferenceZhang, Jing-An; Chen, Yu-Ping. Synthesis of pyruvaldehyde. Jingxi Huagong (2000), 17(9), 507-510.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 Iondetails
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 peroxidedetails
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 peroxidedetails
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 Iondetails
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 + Pyruvaldehydedetails
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 peroxidedetails
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 peroxidedetails
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