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Phenylglyoxal (M2MDB001398)

Record Information
Version2.0
Creation Date2012-05-31 14:52:41 -0600
Update Date2015-06-03 17:20:21 -0600
Secondary Accession Numbers
  • ECMDB20598
Identification
Name:Phenylglyoxal
DescriptionPhenylglyoxal is a member of the chemical class known as Phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. It contains both an aldehyde and a ketone functional group. It is yellow liquid when anhydrous but readily forms a colorless crystalline hydrate. It has been used as a reagent to modify the amino acid, arginine. It is a substrate for the enzyme HcHA or Glyoxylse III. This enzyme catalyzes the conversion of methylglyoxal (MG) to D-lactate in a single glutathione (GSH)-independent step. It can also use phenylglyoxal as substrate and generate phenylactate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • α-oxobenzeneacetaldehyde
  • 2-Oxo-2-phenylacetaldehyde
  • a-Oxobenzeneacetaldehyde
  • Alpha-Oxobenzeneacetaldehyde
  • Benzeneacetaldehyde, α-oxo-, monohydrate
  • Benzeneacetaldehyde, α-oxo-, monohydric acid
  • Benzeneacetaldehyde, a-oxo
  • Benzeneacetaldehyde, a-oxo-, monohydrate
  • Benzeneacetaldehyde, a-oxo-, monohydric acid
  • Benzeneacetaldehyde, alpha-oxo
  • Benzeneacetaldehyde, alpha-oxo-, monohydrate
  • Benzeneacetaldehyde, alpha-oxo-, monohydric acid
  • Benzeneacetaldehyde, α-oxo
  • Benzeneacetaldehyde, α-oxo-, monohydrate
  • Benzeneacetaldehyde, α-oxo-, monohydric acid
  • Benzoylcarboxaldehyde
  • Benzoylformaldehyde
  • Glyoxal, phenyl-
  • Oxo(phenyl)acetaldehyde
  • Phenyl-Glyoxal
  • Phenylethanedione
  • Phenylglyoxal
  • α-Oxobenzeneacetaldehyde
Chemical Formula:C8H6O2
Weight:Average: 134.132
Monoisotopic: 134.036779436
InChI Key:OJUGVDODNPJEEC-UHFFFAOYSA-N
InChI:InChI=1S/C8H6O2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H
CAS number:1074-12-0
IUPAC Name:2-oxo-2-phenylacetaldehyde
Traditional IUPAC Name:phenylglyoxal
SMILES:O=CC(=O)C1=CC=CC=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetaldehydes
Direct ParentPhenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • Aryl ketone
  • Benzoyl
  • Alpha-ketoaldehyde
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point: 76-79 °C (hydrate)
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.96 g/LALOGPS
logP1.34ALOGPS
logP1.62ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)14.32ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.32 m³·mol⁻¹ChemAxon
Polarizability13.09 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-feebf6828b7d7a986412View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-0da9863845ac80a79bc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-3993b9e36bd0e1df8f8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-9e6afa995f5f44145d2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-72cf846fa012eba48134View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4900000000-a9525c4588c184fbddcdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b9f50b78ecb7cc2a2402View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0550-3900000000-a5702883d5a5ca5a6183View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-4900000000-860717ec8d54f5e8e4d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-fbc40c541fd66ff3470dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-0900000000-b3d6c02c7001060eb967View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-4900000000-9eece03c1aa0314a585eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-28ca63be4b8994c5b32cView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID495613
HMDB IDHMDB0061916
Pubchem Compound ID14090
Kegg IDNot Available
ChemSpider ID13470
Wikipedia IDPhenylglyoxal
BioCyc IDPHENYLGLYOXAL
EcoCyc IDPHENYLGLYOXAL

Enzymes

Protein Details
1. Molecular chaperone Hsp31 and glyoxalase 3
General function:
Not Available
Specific function:
Functions as a holding molecular chaperone (holdase) which stabilizes unfolding intermediates and rapidly releases them in an active form once stress has abated. Plays an important role in protecting cells from severe heat shock and starvation, as well as in acid resistance of stationary-phase cells. It uses temperature-induced exposure of structured hydrophobic domains to capture and stabilizes early unfolding and denatured protein intermediates under severe thermal stress. Catalyzes the conversion of methylglyoxal (MG) to D-lactate in a single glutathione (GSH)-independent step. It can also use phenylglyoxal as substrate. Glyoxalase activity protects cells against dicarbonyl stress. Displays an aminopeptidase activity that is specific against peptide substrates with alanine or basic amino acids (lysine, arginine) at N-terminus. Functions as a holding molecular chaperone (holdase) which stabilizes unfolding intermediates and rapidly releases them in an active form once stress has abated. Plays an important role in protecting cells from severe heat shock and starvation, as well as in acid resistance of stationary-phase cells. It uses temperature-induced exposure of structured hydrophobic domains to capture and stabilizes early unfolding and denatured protein intermediates under severe thermal stress. Catalyzes the conversion of methylglyoxal (MG) to D-lactate in a single glutathione (GSH)-independent step. It can also use phenylglyoxal as substrate. Glyoxalase activity protects cells against dicarbonyl stress. Displays an aminopeptidase activity that is specific against peptide substrates with alanine or basic amino acids (lysine, arginine) at N-terminus.
Gene Name:
hchA
Uniprot ID:
P31658
Molecular weight:
Not Available
Reactions
(R)-lactate = methylglyoxal + H(2)O.
(R)-lactate = methylglyoxal + H(2)O.