Record Information
Version2.0
Creation Date2012-05-31 13:57:05 -0600
Update Date2015-09-17 15:41:16 -0600
Secondary Accession Numbers
  • ECMDB02786
Identification
Name:Nitrite
DescriptionA nitrite compound is either a salt or an ester of nitrous acid. Sodium nitrite is used for the curing of meat because it prevents bacterial growth and, in a reaction with the meat's myoglobin, gives the product a desirable dark red color. Nitrite can be reduced to nitric oxide or ammonia by many species of bacteria. Several mechanisms for nitrite conversion to NO have been described including enzymatic reduction by xanthine oxidoreductase and NO synthase (NOS), as well as nonenzymatic acidic disproportionation. -- Wikipedia
Structure
Thumb
Synonyms:
  • Nitrite
  • Nitrite anion
  • Nitrite ion
  • Nitrogen dioxide
  • Nitrogen dioxide ion
  • Nitrogen peroxide ion
  • NO2
  • NO2-
  • NO2
  • NO2-
Chemical Formula:NO2
Weight:Average: 46.0055
Monoisotopic: 45.992903249
InChI Key:IOVCWXUNBOPUCH-UHFFFAOYSA-M
InChI:InChI=1S/HNO2/c2-1-3/h(H,2,3)/p-1
CAS number:14797-65-0
IUPAC Name:nitrous acid
Traditional IUPAC Name:nitrous acid
SMILES:[O-]N=O
Chemical Taxonomy
Description belongs to the class of inorganic compounds known as non-metal nitrites. These are inorganic non-metallic compounds containing a nitrite as its largest oxoanion.
KingdomInorganic compounds
Super ClassHomogeneous non-metal compounds
ClassNon-metal oxoanionic compounds
Sub ClassNon-metal nitrites
Direct ParentNon-metal nitrites
Alternative Parents
Substituents
  • Non-metal nitrite
  • Inorganic nitrite
  • Inorganic oxide
Molecular FrameworkNot Available
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
logP0.17ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.66 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity8.72 m³·mol⁻¹ChemAxon
Polarizability2.81 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2 Hydrogen ion + Nitrate + Ubiquinol-8 > Water + Nitrite + Ubiquinone-8 +2 Hydrogen ion
2 Hydrogen ion + Menaquinol 8 + Nitrate > Water + Menaquinone 8 + Nitrite +2 Hydrogen ion
Ubiquinol-8 + Nitrate > Ubiquinone-8 + Water + Nitrite
Menaquinol 8 + Nitrate > Menaquinone 8 + Water + Nitrite
5 Hydrogen ion + 3 NADH + Nitrite >2 Water +3 NAD + Ammonium
3 Ubiquinol-8 + 2 Hydrogen ion + Nitrite >3 Ubiquinone-8 +2 Water + Ammonium
3 Menaquinol 8 + 2 Hydrogen ion + Nitrite >3 Menaquinone 8 +2 Water + Ammonium
Ammonium hydroxide + 3 NAD + Water + Ammonia <> Nitrite +3 NADH +3 Hydrogen ion
Ammonium hydroxide + 3 NADP + Water <> Nitrite +3 NADPH +3 Hydrogen ion
Nitrite + Acceptor + Water + Acceptor <> Nitrate + Reduced acceptor + Reduced acceptor
2 Ferricytochrome c + Nitrite + Water <> Nitrate +2 Ferrocytochrome c +2 Hydrogen ion
4-Nitrocatechol + Oxygen + 3 Hydrogen ion <> Benzene-1,2,4-triol + Nitrite + Water
Ammonia + 2 Water + 6 Ferricytochrome c + Ferricytochrome c <> Nitrite +6 Ferrocytochrome c +6 Hydrogen ion + Ferrocytochrome c
Nitrobenzene + Oxygen <> Pyrocatechol + Nitrite
Nitrite + Water + Cytochromes-C-Oxidized <> Nitrate + Cytochromes-C-Reduced
a menaquinol + Nitrate + Hydrogen ion > a menaquinone + Nitrite + Water + Hydrogen ion
Nitrate + a ubiquinol > Nitrite + Water + a ubiquinone
Nitrate + Hydrogen ion > Nitrite + Water
NAD(P)H + Nitrite + Hydrogen ion > NAD(P)<sup>+</sup> + Ammonium + Water
Nitrite + acceptor > Nitrate + reduced acceptor
Ammonium hydroxide + 3 NAD(P)(+) + Water > Nitrite +3 NAD(P)H
Ammonia + 2 Water + 6 Ferricytochrome c > Nitrite +6 Ferrocytochrome c +7 Hydrogen ion
Ammonia + NAD + 3 NADP + 2 Water <> Nitrite + NADH +3 NADPH +5 Hydrogen ion
Nitrite + Nitrite > Nitrite
Nitrate + cytochrome c nitrite reductase + Nitrate <> Nitrite + cytochrome c nitrite reductase + Water + Nitrite

SMPDB Pathways:
Nitrogen metabolismPW000755 ThumbThumb?image type=greyscaleThumb?image type=simple
nitrate reduction VIIIPW002092 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0007-9000000000-9cf82c70d7bc0883ea95View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0005-9000000000-e52588fd7e5b6989584dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0007-9000000000-891acfcb7562d9875939View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-701578487c4dc8b94d22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-701578487c4dc8b94d22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-701578487c4dc8b94d22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-9c61b79c18a51c772d86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-9c61b79c18a51c772d86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-9c61b79c18a51c772d86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-f32ca30bef7a838cd1d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-f32ca30bef7a838cd1d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-25fa00bd60fa653bf828View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-a0441e6336543cb88423View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-a0441e6336543cb88423View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-a0441e6336543cb88423View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Nakata, Sumio; Eiki, Toshio; Tanaka, Norihiro; Koyama, Tadashi; Tsukui, Hiroto; Watanabe, Shizuo. Production of nitrite ions from trinitrophenyl myosin and from trinitrophenyl subfragment-1. Journal of Biochemistry (Tokyo, Japan) (1986), 99(1), 27-
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16301
HMDB IDHMDB02786
Pubchem Compound ID24529
Kegg IDC00088
ChemSpider ID921
WikipediaNitrite
BioCyc IDNITRITE
EcoCyc IDNITRITE
Ligand ExpoNO2

Enzymes

General function:
Involved in oxidation-reduction process
Specific function:
Ammonium hydroxide + 3 NAD(P)(+) + H(2)O = nitrite + 3 NAD(P)H
Gene Name:
nirB
Uniprot ID:
P08201
Molecular weight:
93121
Reactions
Ammonium hydroxide + 3 NAD(P)(+) + H(2)O = nitrite + 3 NAD(P)H.
General function:
Involved in oxidoreductase activity
Specific function:
The nitrate reductase enzyme complex allows E.coli to use nitrate as an electron acceptor during anaerobic growth. The alpha chain is the actual site of nitrate reduction
Gene Name:
narG
Uniprot ID:
P09152
Molecular weight:
140489
Reactions
Nitrite + acceptor = nitrate + reduced acceptor.
General function:
Involved in nitrite reductase [NAD(P)H] activity
Specific function:
Required for activity of the reductase
Gene Name:
nirD
Uniprot ID:
P0A9I8
Molecular weight:
12284
Reactions
Ammonium hydroxide + 3 NAD(P)(+) + H(2)O = nitrite + 3 NAD(P)H.
General function:
Involved in nitrogen compound metabolic process
Specific function:
Plays a role in nitrite reduction
Gene Name:
nrfA
Uniprot ID:
P0ABK9
Molecular weight:
53703
Reactions
NH(3) + 2 H(2)O + 6 ferricytochrome c = nitrite + 6 ferrocytochrome c + 7 H(+).
General function:
Involved in nitrate reductase activity
Specific function:
This is a second nitrate reductase enzyme which can substitute for the NRA enzyme and allows E.coli to use nitrate as an electron acceptor during anaerobic growth. The gamma chain is a membrane-embedded heme-iron unit resembling cytochrome b, which transfers electrons from quinones to the beta subunit
Gene Name:
narV
Uniprot ID:
P0AF32
Molecular weight:
26018
Reactions
Nitrite + acceptor = nitrate + reduced acceptor.
General function:
Involved in iron-sulfur cluster binding
Specific function:
The nitrate reductase enzyme complex allows E.coli to use nitrate as an electron acceptor during anaerobic growth. The beta chain is an electron transfer unit containing four cysteine clusters involved in the formation of iron-sulfur centers. Electrons are transferred from the gamma chain to the molybdenum cofactor of the alpha subunit
Gene Name:
narH
Uniprot ID:
P11349
Molecular weight:
58066
Reactions
Nitrite + acceptor = nitrate + reduced acceptor.
General function:
Involved in nitrate reductase activity
Specific function:
The nitrate reductase enzyme complex allows E.coli to use nitrate as an electron acceptor during anaerobic growth. The gamma chain is a membrane-embedded heme-iron unit resembling cytochrome b, which transfers electrons from quinones to the beta subunit
Gene Name:
narI
Uniprot ID:
P11350
Molecular weight:
25497
Reactions
Nitrite + acceptor = nitrate + reduced acceptor.
General function:
Involved in unfolded protein binding
Specific function:
Chaperone required for proper molybdenum cofactor insertion and final assembly of the membrane-bound respiratory nitrate reductase 2
Gene Name:
narW
Uniprot ID:
P19317
Molecular weight:
26160
General function:
Involved in iron-sulfur cluster binding
Specific function:
This is a second nitrate reductase enzyme which can substitute for the NRA enzyme and allows E.coli to use nitrate as an electron acceptor during anaerobic growth. The beta chain is an electron transfer unit containing four cysteine clusters involved in the formation of iron-sulfur centers. Electrons are transferred from the gamma chain to the molybdenum cofactor of the alpha subunit
Gene Name:
narY
Uniprot ID:
P19318
Molecular weight:
58557
Reactions
Nitrite + acceptor = nitrate + reduced acceptor.
General function:
Involved in oxidoreductase activity
Specific function:
The alpha chain is the actual site of nitrate reduction
Gene Name:
narZ
Uniprot ID:
P19319
Molecular weight:
140226
Reactions
Nitrite + acceptor = nitrate + reduced acceptor.
General function:
Involved in oxidoreductase activity
Specific function:
Catalytic subunit of the periplasmic nitrate reductase (NAP). Only expressed at high levels during aerobic growth. NapAB complex receives electrons from the membrane-anchored tetraheme protein napC, thus allowing electron flow between membrane and periplasm. Essential function for nitrate assimilation and may have a role in anaerobic metabolism
Gene Name:
napA
Uniprot ID:
P33937
Molecular weight:
93041
Reactions
Nitrite + acceptor = nitrate + reduced acceptor.
General function:
Involved in electron carrier activity
Specific function:
Involved in electron transfer (Probable)
Gene Name:
napG
Uniprot ID:
P0AAL3
Molecular weight:
24924
General function:
Involved in electron carrier activity
Specific function:
Involved in electron transfer
Gene Name:
napH
Uniprot ID:
P33934
Molecular weight:
31873
General function:
Inorganic ion transport and metabolism
Specific function:
Probably involved in the transfer of electrons from the quinone pool to the type-c cytochromes
Gene Name:
nrfD
Uniprot ID:
P32709
Molecular weight:
35042
General function:
Involved in electron carrier activity
Specific function:
Probably involved in the transfer of electrons from the quinone pool to the type-c cytochromes
Gene Name:
nrfC
Uniprot ID:
P0AAK7
Molecular weight:
24567
General function:
Involved in heme binding
Specific function:
Plays a role in nitrite reduction
Gene Name:
nrfB
Uniprot ID:
P0ABL1
Molecular weight:
20714
General function:
Energy production and conversion
Specific function:
Small subunit of the periplasmic nitrate reductase (NAP). Only expressed at high levels during aerobic growth. NapAB complex receives electrons from the membrane-anchored tetraheme napC protein, thus allowing electron flow between membrane and periplasm. Essential function for nitrate assimilation and may have a role in anaerobic metabolism
Gene Name:
napB
Uniprot ID:
P0ABL3
Molecular weight:
16297
General function:
Involved in heme binding
Specific function:
Mediates electron flow from quinones to the napAB complex
Gene Name:
napC
Uniprot ID:
P0ABL5
Molecular weight:
23100
General function:
Involved in unfolded protein binding
Specific function:
Chaperone required for proper molybdenum cofactor insertion and final assembly of the membrane-bound respiratory nitrate reductase 1. Required for the insertion of the molybdenum into the apo-NarG subunit, maybe by keeping NarG in an appropriate competent-open conformation for the molybdenum cofactor insertion to occur. NarJ maintains the apoNarGH complex in a soluble state. Upon insertion of the molybdenum cofactor, NarJ seems to dissociate from the activated soluble NarGH complex, before its association with the NarI subunit on the membrane
Gene Name:
narJ
Uniprot ID:
P0AF26
Molecular weight:
26449
General function:
Not Available
Specific function:
Not Available
Gene Name:
yeaW
Uniprot ID:
P0ABR7
Molecular weight:
Not Available
General function:
Not Available
Specific function:
Not Available
Gene Name:
nrfE
Uniprot ID:
P32710
Molecular weight:
Not Available

Transporters

General function:
Involved in transporter activity
Specific function:
May act as a nitrite transporter
Gene Name:
nirC
Uniprot ID:
P0AC26
Molecular weight:
28562
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transmembrane transport
Specific function:
Involved in excretion of nitrite produced by the dissimilatory reduction of nitrate
Gene Name:
narK
Uniprot ID:
P10903
Molecular weight:
49693
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368
General function:
Involved in transmembrane transport
Specific function:
Involved in excretion of nitrite produced by the dissimilatory reduction of nitrate
Gene Name:
narU
Uniprot ID:
P37758
Molecular weight:
49890