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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Compound: phenylglyoxal

Synonyms: benzoylcarboxaldehyde, benzoylformaldehyde, phenylethanedione, α-oxobenzeneacetaldehyde, benzeneacetaldehyde, α-oxo-, monohydrate, glyoxal, phenyl-

Chemical Formula: C8H6O2

Molecular Weight: 134.13 Daltons

Monoisotopic Molecular Weight: 134.0367794368 Daltons

SMILES: C1(C=CC(=CC=1)C(=O)C=O)

InChI: InChI=1S/C8H6O2/c9-6-8(10)7-4-2-1-3-5-7/h1-6H

InChIKey: InChIKey=OJUGVDODNPJEEC-UHFFFAOYSA-N

Unification Links: ChEBI:495613 , ChemSpider:13470 , PubChem:14090

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 35.33672 Inferred by computational analysis [Latendresse13]

Enzymes inhibited by phenylglyoxal, sorted by the type of inhibition, are:

Inhibitor (Irreversible) of: pyruvate oxidase [Koland82]

Inhibitor (Mechanism unknown) of: acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase [Green84] , threonine dehydrogenase [Epperly89] , 2-amino-3-ketobutyrate CoA ligase [Mukherjee92] , isocitrate dehydrogenase [Comment 1] , isopenicillin N epimerase [Usui89] , acetate kinase [Latimer93] , uroporphyrinogen decarboxylase [Jones93a]


References

Epperly89: Epperly BR, Dekker EE (1989). "Inactivation of Escherichia coli L-threonine dehydrogenase by 2,3-butanedione. Evidence for a catalytically essential arginine residue." J Biol Chem 1989;264(31);18296-301. PMID: 2681195

Green84: Green PR, Bell RM (1984). "The triose-phosphate site of homogeneous reconstituted sn-glycerol-3-phosphate acyltransferase of Escherichia coli." Biochim Biophys Acta 1984;795(2);348-55. PMID: 6383480

Jones93a: Jones RM, Jordan PM (1993). "Purification and properties of the uroporphyrinogen decarboxylase from Rhodobacter sphaeroides." Biochem J 293 ( Pt 3);703-12. PMID: 8352737

Koland82: Koland JG, O'Brien TA, Gennis RB (1982). "Role of arginine in the binding of thiamin pyrophosphate to Escherichia coli pyruvate oxidase." Biochemistry 21(11);2656-600. PMID: 7046791

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Latimer93: Latimer MT, Ferry JG (1993). "Cloning, sequence analysis, and hyperexpression of the genes encoding phosphotransacetylase and acetate kinase from Methanosarcina thermophila." J Bacteriol 1993;175(21);6822-9. PMID: 8226623

McKee89: McKee JS, Nimmo HG (1989). "Evidence for an arginine residue at the coenzyme-binding site of Escherichia coli isocitrate dehydrogenase." Biochem J 1989;261(1);301-4. PMID: 2673216

Mukherjee92: Mukherjee JJ, Dekker EE (1992). "Inactivation of Escherichia coli 2-amino-3-ketobutyrate CoA ligase by phenylglyoxal and identification of an active-site arginine peptide." Arch Biochem Biophys 299(1);147-53. PMID: 1444446

Usui89: Usui S, Yu CA (1989). "Purification and properties of isopenicillin N epimerase from Streptomyces clavuligerus." Biochim Biophys Acta 999(1);78-85. PMID: 2804141


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Dec 22, 2014, biocyc13.