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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: hydroxylamine

Synonyms: NH2OH

Chemical Formula: H3NO

Molecular Weight: 33.03 Daltons

Monoisotopic Molecular Weight: 33.0214637236 Daltons

SMILES: NO

InChI: InChI=1S/H3NO/c1-2/h2H,1H2

InChIKey: InChIKey=AVXURJPOCDRRFD-UHFFFAOYSA-N

Unification Links: CAS:7803-49-8 , ChEBI:15429 , ChemSpider:766 , HMDB:HMDB03338 , KEGG:C00192 , MetaboLights:MTBLC15429 , PubChem:787

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -8.646637 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

ammonia oxidation I (aerobic) , ammonia oxidation IV (autotrophic ammonia oxidizers) :
4 an oxidized c-type cytochrome[out] + hydroxylamine[in] + H2O[in] → 4 a reduced c-type cytochrome[out] + nitrite[in] + 5 H+[in]

ammonia oxidation II (anaerobic) :
hydrazine + H2O + H+ ← ammonium + hydroxylamine

ammonia oxidation III :
pyruvate + hydroxylamine → pyruvic oxime + H2O

nitrifier denitrification :
hydroxylamine + an oxidized c-type cytochrome → nitric oxide + a reduced c-type cytochrome + 3 H+

Not in pathways:
ammonium + an oxidized electron acceptor + H2O ← hydroxylamine + a reduced electron acceptor + H+
hydroxylamine + 4 an oxidized c-type cytochrome + oxygen → nitrite + 4 a reduced c-type cytochrome + H2O + H+

Reactions known to produce the compound:

ammonia oxidation I (aerobic) , ammonia oxidation III , ammonia oxidation IV (autotrophic ammonia oxidizers) :
ammonia[in] + a reduced electron acceptor[in] + oxygen[in]hydroxylamine[in] + an oxidized electron acceptor[in] + H2O[in]

Reactions known to both consume and produce the compound:

ammonia oxidation II (anaerobic) :
nitrite + a reduced electron acceptor + 3 H+hydroxylamine + an oxidized electron acceptor + H2O

In Reactions of unknown directionality:

Not in pathways:
ammonium + NAD+ + H2O = hydroxylamine + NADH + 2 H+
hydroxylamine + L-asparagine + H+ = ammonium + β-L-aspartylhydroxamate
2 hydroxylamine + 2 NAD+ = hyponitrous acid + 2 NADH + 2 H+

In Redox half-reactions:
ammonium + oxygen + H+ + 2 e-hydroxylamine + H2O ,
nitrite[in] + 5 H+[in] + 4 e-hydroxylamine[in] + H2O[in] ,
ammonia[in] + oxygen[in] + 2 H+[in] + 2 e-hydroxylamine[in] + H2O[in] ,
hydroxylamine[in] + 3 H+[in] + 2 e- → ammonium[in] + H2O[in]

Enzymes activated by hydroxylamine, sorted by the type of activation, are:

Activator (Non-allosteric) of: pyruvic oxime dioxygenase [Ono96]

Activator (Mechanism unknown) of: cystathionine β-synthase [Kimura71]

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

Inhibitor (Competitive) of: hydrazine oxidoreductase [Shimamura07] , hydrazine oxidoreductase [Shimamura07] , adenylosuccinate synthetase [Comment 1] , glutamate dehydrogenase (NAD-dependent) [Bonete89, Comment 2] , glutamate dehydrogenase (NADP-dependent) [Comment 3] , canaline reductase [Rosenthal92]

Inhibitor (Irreversible) of: aralkylamine dehydrogenase [Govindaraj94]

Inhibitor (Mechanism unknown) of: aspartate 1-decarboxylase [Cronan80] , phosphatidylserine decarboxylase [Comment 4] , N-succinyldiaminopimelate aminotransferase [Peterkofsky61] , 4-aminobutyrate transaminase [Schulz90] , cytochrome bo terminal oxidase [Kita86, Helmward89] , cytochrome bd-I terminal oxidase [Kita86, Helmward89] , 3-chloro-D-alanine dehydrochlorinase [Nagasawa85] , phenylethylamine oxidase [Roh94] , alanine racemase [Nomura01] , D-serine ammonia-lyase [Tanaka08a] , S-alk(en)-L-cysteine sulfoxide lyase [Manabe98] , N8-acetylspermidine oxidase [Shukla92] , N-acetylneuraminate synthase [Komaki97] , isopenicillin N epimerase [Usui89] , L-lysine-α-ketoglutarate reductase [Hutzler75] , porphobilinogen deaminase [Jones94] , methylamine dehydrogenase [Kenney83] , mimosine synthase [Ikegami90] , 2-aminoethylphosphonate aminotransferase [Dumora83] , tryptophan 2'-dioxygenase [Roberts77a] , D-lactate dehydrogenase [Schweiger84] , β-cyano-L-alanine synthase [Ikegami88] , tryptophan dioxygenase [Matsumura84] , O-acetylhomoserine sulfhydrylase [Yamagata94] , willardiine synthase [Murakoshi78] , isowillardiine synthase [Murakoshi78] , lactyl-CoA dehydratase [Schweiger84, Schweiger85] , taurine:α-ketoglutarate aminotransferase [Toyama78] , methionine γ-lyase [Esaki87] , tryptophan 2-monooxygenase [Kosuge66] , D-ornithine aminomutase [Somack73] , L-arginine decarboxyoxidase [Bera87] , arginine racemase [Yorifuji71] , 4-hydroxyglutamate transaminase [GOLDSTONE62] , hydroxyproline 2-epimerase [Adams64] , putrescine oxidase [Adachi66a] , L-α-aminoadipate δ-semialdehyde:NAD oxidoreductase [Rodwell71] , L-sorbosone dehydrogenase [Asakura99] , tellimagrandin II: O2 oxidoreductase [Niemetz03b] , L-lysine:pyruvate aminotransferase [Schmidt87a] , alanine aminotransferase [Umemura94]

Inhibitor (Other types) of: N-methyl-L-glutamate synthase [Pollock71] , N-methyl-L-glutamate synthase [Pollock71] , β-pyrazole-1-ylalanine synthase [Murakoshi84] , L-tyrosine decarboxylase [Kezmarsky05] , β-methylaspartate aminotransferase [Phillips72] , imidazole propionase [Feinberg59] , urocanase [Phillips71] , L-allo-threonine aldolase [Kataoka97]


References

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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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