<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-07-30 14:55:01 -0600</creation_date>
  <update_date>2015-06-03 17:20:57 -0600</update_date>
  <accession>ECMDB21231</accession>
  <m2m_id>M2MDB001639</m2m_id>
  <name>Hydrogen cyanide</name>
  <description>HCN is formed in interstellar clouds through one of two major pathways: via a neutral-neutral reaction (CH2 + N &lt;=&gt; HCN + H) and via dissociative recombination (HCNH+ + e- &lt;=&gt; HCN + H). The dissociative recombination pathway is dominant by 30%; however, the HCNH+ must be in its linear form. Dissociative recombination with its structural isomer, H2NC+ produces hydrogen isocyanide (HNC), exclusively.; HCN is produced on an industrial scale and is a highly valuable precursor to many chemical compounds ranging from polymers to pharmaceuticals.; Hydrogen cyanide (with the historical common name of Prussic acid) is an inorganic compound with chemical formula HCN. It is a colorless, extremely poisonous liquid that boils slightly above room temperature at 26 </description>
  <synonyms>
    <synonym>AC</synonym>
    <synonym>Acide cyanhydrique</synonym>
    <synonym>Acido cianidrico</synonym>
    <synonym>Aero Liquid HCN</synonym>
    <synonym>Agent AC</synonym>
    <synonym>Blausaeure</synonym>
    <synonym>Blausaeure (German)</synonym>
    <synonym>Blausaure</synonym>
    <synonym>Blauwzuur</synonym>
    <synonym>Carbon hydride nitride</synonym>
    <synonym>Carbon hydride nitride (CHN)</synonym>
    <synonym>Cn-, cyano</synonym>
    <synonym>Cyaanwaterstof</synonym>
    <synonym>Cyanide</synonym>
    <synonym>Cyanwasserstoff</synonym>
    <synonym>Cyclon</synonym>
    <synonym>Cyclone B</synonym>
    <synonym>Cyjanowodor</synonym>
    <synonym>Evercyn</synonym>
    <synonym>Formic anammonide</synonym>
    <synonym>Formonitrile</synonym>
    <synonym>HCN</synonym>
    <synonym>Hydridonitridocarbon</synonym>
    <synonym>Hydrocyanate</synonym>
    <synonym>Hydrocyanic acid</synonym>
    <synonym>Hydrogen cyanide</synonym>
    <synonym>Hydrogen(nitridocarbonate)</synonym>
    <synonym>Hydrogen(nitridocarbonic acid)</synonym>
    <synonym>Methanenitrile</synonym>
    <synonym>Nitrilomethane</synonym>
    <synonym>Prussate</synonym>
    <synonym>Prussate, unstabilized</synonym>
    <synonym>Prussic Acid</synonym>
    <synonym>Prussic acid, unstabilized</synonym>
    <synonym>Zaclondiscoids</synonym>
    <synonym>Zootate</synonym>
    <synonym>Zootic acid</synonym>
    <synonym>[CHN]</synonym>
  </synonyms>
  <chemical_formula>CHN</chemical_formula>
  <average_molecular_weight>27.0253</average_molecular_weight>
  <monisotopic_moleculate_weight>27.010899037</monisotopic_moleculate_weight>
  <iupac_name>formonitrile</iupac_name>
  <traditional_iupac>hydrogen cyanide</traditional_iupac>
  <cas_registry_number>74-90-8</cas_registry_number>
  <smiles>C#N</smiles>
  <inchi>InChI=1S/CHN/c1-2/h1H</inchi>
  <inchikey>LELOWRISYMNNSU-UHFFFAOYSA-N</inchikey>
  <state>Liquid</state>
  <cellular_locations>
    <cellular_location>Cytosol</cellular_location>
    <cellular_location>Extra-organism</cellular_location>
    <cellular_location>Periplasm</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.26e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>-13.4 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.35</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>9.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>formonitrile</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>27.0253</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>27.010899037</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>C#N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>CHN</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/CHN/c1-2/h1H</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>LELOWRISYMNNSU-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>23.79</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>7.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>2.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
    <pathway>
      <name>Thiosulfate Disproportionation III</name>
      <description>Thiosulfate sulfurtransferase is more often referred to by the name rhodanese, from the German word for thiocyanate, "rhodanid". The enzyme catalyzes the transfer of a sulfur atom from suitable sulfur donors to nucleophilic sulfur acceptors. The original description of rhodanese, purified from bovine mitochondria, used thiosulfate and cyanide for this purpose. Rhodanese is a widespread enzyme, and has been detected in many major phyla, both prokaryotic and eukaryotic. Despite its ubiquity, the physiological role of rhodanese has not yet been established unambiguously. It has been suggested that rhodanese is involved in detoxification of cyanide in both mammals and bacteria. It has also been proposed that rhodanese, using the dithiol dihydrolipoate as the sulfur acceptor, may act as a sulfur insertase involved in the formation of prosthetic groups in iron-sulfur proteins, such as ferredoxin. (EcoCyc)</description>
      <pathwhiz_id>PW002060</pathwhiz_id>
      <kegg_map_id/>
      <subject>Metabolic</subject>
    </pathway>
    <pathway>
      <name>thiosulfate disproportionation III (rhodanese)</name>
      <ecocyc_pathway_id>PWY-5350</ecocyc_pathway_id>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>34474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>172526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56882</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>56891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16042</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id/>
  <pubchem_compound_id>768</pubchem_compound_id>
  <chemspider_id>748</chemspider_id>
  <kegg_id>C01326</kegg_id>
  <chebi_id>18407</chebi_id>
  <biocyc_id>HCN</biocyc_id>
  <het_id>CYN</het_id>
  <wikipidia>Hydrogen_cyanide</wikipidia>
  <foodb_id/>
  <general_references>
    <reference>
      <reference_text>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.</reference_text>
      <pubmed_id>21097882</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference/>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>Thiosulfate sulfurtransferase glpE</name>
      <uniprot_id>P0A6V5</uniprot_id>
      <uniprot_name>GLPE_ECOLI</uniprot_name>
      <gene_name>glpE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0A6V5.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>3-mercaptopyruvate sulfurtransferase</name>
      <uniprot_id>P31142</uniprot_id>
      <uniprot_name>THTM_ECOLI</uniprot_name>
      <gene_name>sseA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P31142.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Thiosulfate sulfurtransferase YnjE</name>
      <uniprot_id>P78067</uniprot_id>
      <uniprot_name>YNJE_ECOLI</uniprot_name>
      <gene_name>ynjE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P78067.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Thiosulfate sulfurtransferase PspE</name>
      <uniprot_id>P23857</uniprot_id>
      <uniprot_name>PSPE_ECOLI</uniprot_name>
      <gene_name>pspE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P23857.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
    <enzyme>
      <name>Outer membrane protein N</name>
      <uniprot_id>P77747</uniprot_id>
      <uniprot_name>OMPN_ECOLI</uniprot_name>
      <gene_name>ompN</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P77747.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Outer membrane pore protein E</name>
      <uniprot_id>P02932</uniprot_id>
      <uniprot_name>PHOE_ECOLI</uniprot_name>
      <gene_name>phoE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02932.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Outer membrane protein F</name>
      <uniprot_id>P02931</uniprot_id>
      <uniprot_name>OMPF_ECOLI</uniprot_name>
      <gene_name>ompF</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02931.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Outer membrane protein C</name>
      <uniprot_id>P06996</uniprot_id>
      <uniprot_name>OMPC_ECOLI</uniprot_name>
      <gene_name>ompC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P06996.xml</protein_url>
    </enzyme>
  </transporters>
  <reactions>
    <reaction_text>Hydrogen cyanide + Thiosulfate &gt; Hydrogen ion + Sulfite + Thiocyanate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Hydrogen cyanide + 3-Mercaptopyruvic acid + Cyanide &lt;&gt; Hydrogen ion + Pyruvic acid + Thiocyanate</reaction_text>
    <kegg_reaction_id>R03106</kegg_reaction_id>
    <ecocyc_id>MERCAPYSTRANS-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Hydrogen cyanide + 3-Mercaptopyruvic acid &lt;&gt; Thiocyanate + Pyruvic acid</reaction_text>
    <kegg_reaction_id>R03106</kegg_reaction_id>
    <ecocyc_id>MERCAPYSTRANS-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Hydrogen cyanide + 3-Mercaptopyruvic acid  Hydrogen ion + Pyruvic acid + Thiocyanate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>MERCAPYSTRANS-RXN</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>&lt;i&gt;S&lt;/i&gt;-sulfanyl-[acceptor] + Hydrogen cyanide  an unsulfurated sulfur acceptor + Thiocyanate + Hydrogen ion</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>RXN0-6359</ecocyc_id>
    <pw_reaction_id/>
    <reaction_text>Thiosulfate + Hydrogen cyanide &gt; Sulfite + Thiocyanate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>3-Mercaptopyruvic acid + Hydrogen cyanide &gt; Pyruvic acid + Thiocyanate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Hydrogen cyanide + Thiosulfate &gt; Thiocyanate + Sulfite +2 Hydrogen ion</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id>PW_R006013</pw_reaction_id>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
