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MetaCyc Compound: nitrite

Synonyms: NO2, NO2-

Superclasses: an ionan anionan inorganic anion
an ionan inorganic ionan inorganic anion

Chemical Formula: NO2

Molecular Weight: 46.005 Daltons

Monoisotopic Molecular Weight: 47.0007282815 Daltons

nitrite compound structure

SMILES: N([O-])=O

InChI: InChI=1S/HNO2/c2-1-3/h(H,2,3)/p-1

InChIKey: InChIKey=IOVCWXUNBOPUCH-UHFFFAOYSA-M

Unification Links: CAS:7697-37-2, CAS:14797-65-0, ChEBI:16301, ChemSpider:921, HMDB:HMDB02786, IAF1260:33805, KEGG:C00088, MetaboLights:MTBLC16301, PubChem:946

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -65.91206Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

alkylnitronates degradation , nitrate reduction V (assimilatory) :
ammonium + 3 NAD(P)+ + 2 H2O ← nitrite + 3 NAD(P)H + 5 H+

ammonia oxidation II (anaerobic) , nitrifier denitrification , nitrite-dependent anaerobic methane oxidation :
nitric oxide + an oxidized c-type cytochrome + H2O ← nitrite + a reduced c-type cytochrome + 2 H+

nitrate reduction I (denitrification) :
nitrate[periplasm] + nitrite[cytosol] → nitrate[cytosol] + nitrite[periplasm]

nitrate reduction II (assimilatory) , nitrate reduction VI (assimilatory) :
ammonium + 6 an oxidized ferredoxin [iron-sulfur] cluster + 2 H2O ← nitrite + 6 a reduced ferredoxin [iron-sulfur] cluster + 8 H+

nitrate reduction IV (dissimilatory) :
nitrite[out] + 6 a reduced c-type cytochrome[out] + 8 H+[out] → ammonium[out] + 6 an oxidized c-type cytochrome[out] + 2 H2O[out]

nitrate reduction VII (denitrification) :
nitrate[periplasm] + nitrite[cytosol] → nitrate[cytosol] + nitrite[periplasm]
nitric oxide + an oxidized c-type cytochrome + H2O ← nitrite + a reduced c-type cytochrome + 2 H+

nitrite oxidation :
2 an oxidized c-type cytochrome[out] + nitrite[in] + H2O[in] → 2 a reduced c-type cytochrome[out] + nitrate[in] + 2 H+[in]

nitrite reduction (hemoglobin) :
a ferrohemoglobin + nitrite + H+ → a ferrihemoglobin + nitric oxide + OH-

Not in pathways:
ammonium + 3 NAD+ + 2 H2O ← nitrite + 3 NADH + 5 H+

Reactions known to produce the compound:

1-chloro-2-nitrobenzene degradation :
1-chloro-2-nitrobenzene + NADH + oxygen → 3-chlorocatechol + nitrite + NAD+

2,4,6-trinitrophenol and 2,4-dinitrophenol degradation :
O-[5-(hydroxynitroso)-3-(oxidonitroso)-2-oxocyclohexylidenenitroso]oxidanidolate → O-[5-(oxidonitroso)-4-oxocyclohex-2-en-1-ylidenenitroso]oxidanidolate + nitrite + H+

2,4-dinitrotoluene degradation :
2,4-dinitrotoluene + NADH + oxygen → 4-methyl-5-nitrocatechol + nitrite + NAD+
4-methyl-5-nitrocatechol + NAD(P)H + oxygen → 2-hydroxy-5-methylquinone + nitrite + NAD(P)+ + H+ + H2O

2,6-dinitrotoluene degradation :
2,6-dinitrotoluene + NADH + oxygen → 3-methyl-4-nitrocatechol + nitrite + NAD+

2-nitrophenol degradation :
2-nitrophenol + 2 NADPH + oxygen + 2 H+ → catechol + nitrite + 2 NADP+ + H2O

2-nitrotoluene degradation :
2-nitrotoluene + NADH + oxygen → 3-methylcatechol + nitrite + NAD+

4-nitrophenol degradation I :
4-nitrophenol + NAD(P)H + oxygen + H+ → 1,4-benzoquinone + nitrite + NAD(P)+ + H2O

4-nitrophenol degradation II :
4-nitrocatechol + NAD(P)H + oxygen → 2-hydroxy-1,4-benzoquinone + nitrite + NAD(P)+ + H2O + H+

5-nitroanthranilate degradation :
4-nitro-6-oxohepta-2,4-dienedioate → 2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite

alkylnitronates degradation :
ethylnitronate + oxygen → acetaldehyde + nitrite + [unspecified degradation products]

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 III :
pyruvic oxime + oxygen → pyruvate + nitrite + H+

nitrate reduction II (assimilatory) :
nitrite + NAD+ + H2O ← nitrate + NADH + H+

nitrate reduction III (dissimilatory) , nitrate reduction IX (dissimilatory) , nitrate reduction VIII (dissimilatory) :
nitrate + a menaquinol[inner membrane] + 2 H+nitrite + a menaquinone[inner membrane] + H2O + 2 H+[periplasm]

nitrate reduction IV (dissimilatory) :
nitrate[periplasm] + 2 a reduced c-type cytochrome[periplasm] + 2 H+[periplasm]nitrite[periplasm] + 2 an oxidized c-type cytochrome[periplasm] + H2O[periplasm]

nitrate reduction V (assimilatory) :
nitrite + NADP+ + H2O ← nitrate + NADPH + H+

nitrate reduction VI (assimilatory) :
nitrite + 2 an oxidized ferredoxin [iron-sulfur] cluster + H2O ← nitrate + 2 a reduced ferredoxin [iron-sulfur] cluster + 2 H+

nitrate reduction X (periplasmic, dissimilatory) :
nitrate[periplasm] + an ubiquinol[inner membrane]nitrite[periplasm] + a ubiquinone[inner membrane] + H2O[periplasm]

nitrobenzene degradation II :
nitrobenzene + NADH + oxygen → catechol + nitrite + NAD+

nitroethane degradation :
nitroethane + oxygen + H2O → acetaldehyde + nitrite + hydrogen peroxide + H+

nitroglycerin degradation :
nitroglycerin + NAD(P)H → nitrite + 1,2-dinitroglycerol + NAD(P)+
nitroglycerin + NAD(P)H → 1,3-dinitroglycerol + nitrite + NAD(P)+
1,3-dinitroglycerol + NAD(P)H → 1-mononitroglycerol + nitrite + NAD(P)+
1,2-dinitroglycerol + NAD(P)H → 1-mononitroglycerol + nitrite + NAD(P)+

Reactions known to both consume and produce the compound:

ammonia oxidation II (anaerobic) :
nitrite + 2 an reduced unknown electron acceptor + H+ ↔ hydroxylamine + 2 an oxidized unknown electron acceptor + H2O

nitrate reduction I (denitrification) :
nitrate + an electron-transfer quinol[inner membrane]nitrite + an electron-transfer quinone[inner membrane] + H2O
nitrite[periplasm] + a reduced cytochrome c551[periplasm] + 2 H+[periplasm] ↔ nitric oxide[periplasm] + an oxidized cytochrome c551[periplasm] + H2O[periplasm]

nitrate reduction VII (denitrification) :
nitrate + an electron-transfer quinol[inner membrane]nitrite + an electron-transfer quinone[inner membrane] + H2O

In Reactions of unknown directionality:

Not in pathways:
1-mononitroglycerol + NAD(P)H = glycerol + nitrite + NAD(P)+
2-mononitroglycerol + NAD(P)H = glycerol + nitrite + NAD(P)+
2,4-dinitrophenol + NADH = 4-nitrophenol + nitrite + NAD+
1-chloro-3-nitrobenzene + NADH + oxygen = 4-chlorocatechol + nitrite + NAD+
1-chloro-3-nitrobenzene + NADH + oxygen = 3-chlorocatechol + nitrite + NAD+
2,3-dinitrotoluene + NADH + oxygen = 4-methyl-3-nitrocatechol + nitrite + NAD+
2,4-dinitrotoluene + NADH + oxygen = 4-methyl-3-nitrocatechol + nitrite + NAD+
4-nitrotoluene + NADH + oxygen = 4-methylcatechol + nitrite + NAD+
3,4-dinitrotoluene + NADH + oxygen = 4-methyl-6-nitrocatechol + nitrite + NAD+
1,3-dinitrobenzene + NADH + oxygen = 4-nitrocatechol + nitrite + NAD+
1,4-dinitrobenzene + NADH + oxygen = 4-nitrocatechol + nitrite + NAD+
2-chloro-4-nitrotoluene + NADH + oxygen = 3-chloro-4-methylcatechol + nitrite + NAD+
2-chloro-6-nitrotoluene + NADH + oxygen = 4-chloro-3-methylcatechol + nitrite + NAD+
3 nitrite + 2 H+ = 2 nitric oxide + nitrate + H2O
nitrite + an oxidized unknown electron acceptor + H2O = nitrate + an reduced unknown electron acceptor
nitrite + NAD(P)+ + H2O = nitrate + NAD(P)H + H+

In Transport reactions:
nitrite[cytosol] + H+[periplasm]nitrite[periplasm] + H+[cytosol],
nitrite[cytosol]nitrite[periplasm]

In Redox half-reactions:
nitrate[out] + 2 H+[out] + 2 e-[membrane]nitrite[out] + H2O[out],
nitrate[in] + 2 H+[in] + 2 e-[membrane]nitrite[in] + H2O[in],
nitrite[in] + 8 H+[in] + 6 e-[membrane] → ammonium[in] + 2 H2O[in],
nitrite[out] + 8 H+[out] + 6 e-[membrane] → ammonium[out] + 2 H2O[out],
nitrite[out] + 2 H+[out] + e-[membrane] → nitric oxide[out] + H2O[out],
nitrite[in] + 5 H+[in] + 4 e-[membrane] → hydroxylamine[in] + H2O[in]

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

Inhibitor (Competitive) of: cyanase [Little87, Comment 1], ethylnitronate monooxygenase [Francis09] Inhibitor (Mechanism unknown) of: formate dehydrogenase [Axley90], nitrogenase [Meyer81], NAD-dependent formate dehydrogenase [Jollie91]

References

Axley90: Axley MJ, Grahame DA, Stadtman TC (1990). "Escherichia coli formate-hydrogen lyase. Purification and properties of the selenium-dependent formate dehydrogenase component." J Biol Chem 1990;265(30);18213-8. PMID: 2211698

Francis09: Francis K, Gadda G (2009). "Kinetic evidence for an anion binding pocket in the active site of nitronate monooxygenase." Bioorg Chem 37(5);167-72. PMID: 19683782

Jollie91: Jollie DR, Lipscomb JD (1991). "Formate dehydrogenase from Methylosinus trichosporium OB3b. Purification and spectroscopic characterization of the cofactors." J Biol Chem 266(32);21853-63. PMID: 1657982

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

Little87: Little RM, Anderson PM (1987). "Structural properties of cyanase. Denaturation, renaturation, and role of sulfhydryls and oligomeric structure in catalytic activity." J Biol Chem 1987;262(21);10120-6. PMID: 3301828

Meyer81: Meyer J (1981). "Comparison of carbon monoxide, nitric oxide, and nitrite as inhibitors of the nitrogenase from Clostridium pasteurianum." Arch Biochem Biophys 1981;210(1);246-56. PMID: 6945823


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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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