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MetaCyc Compound: carboxymethoxylamine

Synonyms: aminooxyacetate, (aminooxy)acetic acid, (aminooxy)acetate, hydroxylamine-O-acetic acid

Chemical Formula: C2H4NO3

Molecular Weight: 90.058 Daltons

Monoisotopic Molecular Weight: 91.02694303199999 Daltons

carboxymethoxylamine compound structure

SMILES: C(ON)C([O-])=O

InChI: InChI=1S/C2H5NO3/c3-6-1-2(4)5/h1,3H2,(H,4,5)/p-1

InChIKey: InChIKey=NQRKYASMKDDGHT-UHFFFAOYSA-M

Unification Links: CAS:645-88-5 , ChemSpider:279 , PubChem:285

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -61.867588 Inferred by computational analysis [Latendresse13]

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

Inhibitor (Competitive) of: canaline reductase [Rosenthal92a]

Inhibitor (Mechanism unknown) of: glutamate-1-semialdehyde aminotransferase [Ilag91] , 4-aminobutyrate transaminase [Schulz90] , D-serine ammonia-lyase [Tanaka08] , alanine aminotransferase [Umemura94] , tyrosine aminotransferase [DeEknamkul87] , tyrosine aminotransferase [DeEknamkul87] , 2-aminoethylphosphonate aminotransferase [Dumora83] , β-cyano-L-alanine synthase [Comment 1] , asparagine aminotransferase [Ireland83]

Inhibitor (Other types) of: β-methylaspartate aminotransferase [Phillips72]


References

DeEknamkul87: De-Eknamkul W, Ellis BE (1987). "Tyrosine aminotransferase: the entrypoint enzyme of the tyrosine-derived pathway in rosmarinic acid biosynthesis." Phytochemistry, 26(7), 1941-1946.

Dumora83: Dumora C, Lacoste AM, Cassaigne A (1983). "Purification and properties of 2-aminoethylphosphonate:pyruvate aminotransferase from Pseudomonas aeruginosa." Eur J Biochem 1983;133(1);119-25. PMID: 6406228

Ilag91: Ilag LL, Jahn D, Eggertsson G, Soll D (1991). "The Escherichia coli hemL gene encodes glutamate 1-semialdehyde aminotransferase." J Bacteriol 1991;173(11);3408-13. PMID: 2045363

Ireland83: Ireland RJ, Joy KW (1983). "Purification and properties of an asparagine aminotransferase from Pisum sativum leaves." Arch Biochem Biophys 223(1);291-6. PMID: 6407397

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

Macadam84: Macadam AM, Knowles CJ "Purification and properties of β-cyano-L-alanine synthase from the cyanide-producing bacterium, Chromobacterium violaceum." Biochimica et Biophysica Acta 786:123-132 (1984).

Phillips72: Phillips AT, Nuss JI, Moosic J, Foshay C (1972). "Alternate pathway for isoleucine biosynthesis in Escherichia coli." J Bacteriol 109(2);714-9. PMID: 4550817

Rosenthal92a: Rosenthal GA (1992). "Purification and characterization of the higher plant enzyme L-canaline reductase." Proc Natl Acad Sci U S A 89(5);1780-4. PMID: 1542671

Schulz90: Schulz A, Taggeselle P, Tripier D, Bartsch K (1990). "Stereospecific production of the herbicide phosphinothricin (glufosinate) by transamination: isolation and characterization of a phosphinothricin-specific transaminase from Escherichia coli." Appl Environ Microbiol 1990;56(1);1-6. PMID: 2178550

Tanaka08: Tanaka H, Yamamoto A, Ishida T, Horiike K (2008). "D-Serine dehydratase from chicken kidney: a vertebral homologue of the cryptic enzyme from Burkholderia cepacia." J Biochem 143(1);49-57. PMID: 17977854

Umemura94: Umemura I, Yanagiya K, Komatsubara S, Sato T, Tosa T (1994). "Purification and some properties of alanine aminotransferase from Candida maltosa." Biosci Biotechnol Biochem 58(2);283-7. PMID: 7764540


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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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