MetaCyc Compound: phosphonoacetaldehyde

Synonyms: 2-phosphonoacetaldehyde, phosphonic acid, (2-oxoethyl)-, acetylphosphonate

Superclasses: an organophosphorus compound an organophosphonate

Citations: [Woodyer07]

Chemical Formula: C2H4O4P

Molecular Weight: 123.02 Daltons

Monoisotopic Molecular Weight: 123.9925451589 Daltons

phosphonoacetaldehyde compound structure

SMILES: [CH](CP([O-])(O)=O)=O

InChI: InChI=1S/C2H5O4P/c3-1-2-7(4,5)6/h1H,2H2,(H2,4,5,6)/p-1


Unification Links: ChEBI:58383 , KEGG:C03167 , PubChem:25245167

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -196.00757 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

2-aminoethylphosphonate biosynthesis :
phosphonoacetaldehyde + an aminated amino group donor → (2-aminoethyl)phosphonate + a deaminated amino group donor

2-aminoethylphosphonate degradation II :
phosphonoacetaldehyde + NAD+ + H2O → phosphonoacetate + NADH + 2 H+

rhizocticin A and B biosynthesis :
phosphonoacetaldehyde + oxaloacetate + H+ → 2-keto-4-hydroxy-5-phosphonopentanoate + CO2

Reactions known to produce the compound:

2-aminoethylphosphonate biosynthesis , dehydrophos biosynthesis , fosfomycin biosynthesis , phosphinothricin tripeptide biosynthesis , rhizocticin A and B biosynthesis :
3-phosphonopyruvate + H+phosphonoacetaldehyde + CO2

Reactions known to both consume and produce the compound:

2-aminoethylphosphonate degradation I :
pyruvate + (2-aminoethyl)phosphonate ↔ L-alanine + phosphonoacetaldehyde
phosphonoacetaldehyde + H2O ↔ acetaldehyde + phosphate + H+

2-aminoethylphosphonate degradation II :
pyruvate + (2-aminoethyl)phosphonate ↔ L-alanine + phosphonoacetaldehyde

dehydrophos biosynthesis , fosfomycin biosynthesis , phosphinothricin tripeptide biosynthesis :
2-hydroxyethylphosphonate + NAD+phosphonoacetaldehyde + NADH + H+

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

Inhibitor (Competitive) of: pyruvate oxidase [OBrien80]


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

OBrien80: O'Brien TA, Kluger R, Pike DC, Gennis RB (1980). "Phosphonate analogues of pyruvate. Probes of substrate binding to pyruvate oxidase and other thiamin pyrophosphate-dependent decarboxylases." Biochim Biophys Acta 613(1);10-7. PMID: 6990987

Woodyer07: Woodyer RD, Li G, Zhao H, van der Donk WA (2007). "New insight into the mechanism of methyl transfer during the biosynthesis of fosfomycin." Chem Commun (Camb) NIL(4);359-61. PMID: 17220970

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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