ECMDB: Phenylglyoxal (ECMDB20598) (M2MDB001398)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (1)

Record Information

Version

2.0

Creation Date

2012-05-31 14:52:41 -0600

Update Date

2015-06-03 17:20:21 -0600

Secondary Accession Numbers

ECMDB20598

Identification

Name:

Phenylglyoxal

Description

Phenylglyoxal 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

MOL SDF PDB SMILES InChI

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetaldehydes

Direct Parent

Phenylacetaldehydes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

a small molecule (PHENYLGLYOXAL )

Physical Properties

State:

Solid

Charge:

Melting point:

76-79 °C (hydrate)

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	1.96 g/L	ALOGPS
logP	1.34	ALOGPS
logP	1.62	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	14.32	ChemAxon
pKa (Strongest Basic)	-7.8	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	2	ChemAxon
Refractivity	37.32 m³·mol⁻¹	ChemAxon
Polarizability	13.09 Å³	ChemAxon
Number of Rings	1	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

Reactions:

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-feebf6828b7d7a986412	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-0da9863845ac80a79bc4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2900000000-3993b9e36bd0e1df8f8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-9e6afa995f5f44145d2e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-72cf846fa012eba48134	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4900000000-a9525c4588c184fbddcd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-b9f50b78ecb7cc2a2402	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0550-3900000000-a5702883d5a5ca5a6183	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-4900000000-860717ec8d54f5e8e4d1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9100000000-fbc40c541fd66ff3470d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a59-0900000000-b3d6c02c7001060eb967	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-057i-4900000000-9eece03c1aa0314a585e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-28ca63be4b8994c5b32c	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View 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

Links

External Links:

Resource	Link
CHEBI ID	495613
HMDB ID	HMDB0061916
Pubchem Compound ID	14090
Kegg ID	Not Available
ChemSpider ID	13470
Wikipedia ID	Phenylglyoxal
BioCyc ID	PHENYLGLYOXAL
EcoCyc ID	PHENYLGLYOXAL

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.

Phenylglyoxal (ECMDB20598) (M2MDB001398)

Structure for #<Compound:0x63c79a8>

Enzymes

Reactions