Record Information
Version2.0
Creation Date2012-07-30 14:55:01 -0600
Update Date2015-06-03 17:20:57 -0600
Secondary Accession Numbers
  • ECMDB21231
Identification
Name:Hydrogen cyanide
Description:HCN is formed in interstellar clouds through one of two major pathways: via a neutral-neutral reaction (CH2 + N <=> HCN + H) and via dissociative recombination (HCNH+ + e- <=> 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
Structure
Thumb
Synonyms:
  • AC
  • Acide cyanhydrique
  • Acido cianidrico
  • Aero Liquid HCN
  • Agent AC
  • Blausaeure
  • Blausaeure (German)
  • Blausaure
  • Blauwzuur
  • Carbon hydride nitride
  • Carbon hydride nitride (CHN)
  • Cn-, cyano
  • Cyaanwaterstof
  • Cyanide
  • Cyanwasserstoff
  • Cyclon
  • Cyclone B
  • Cyjanowodor
  • Evercyn
  • Formic anammonide
  • Formonitrile
  • HCN
  • Hydridonitridocarbon
  • Hydrocyanate
  • Hydrocyanic acid
  • Hydrogen cyanide
  • Hydrogen(nitridocarbonate)
  • Hydrogen(nitridocarbonic acid)
  • Methanenitrile
  • Nitrilomethane
  • Prussate
  • Prussate, unstabilized
  • Prussic Acid
  • Prussic acid, unstabilized
  • Zaclondiscoids
  • Zootate
  • Zootic acid
  • [CHN]
Chemical Formula:CHN
Weight:Average: 27.0253
Monoisotopic: 27.010899037
InChI Key:LELOWRISYMNNSU-UHFFFAOYSA-N
InChI:InChI=1S/CHN/c1-2/h1H
CAS number:74-90-8
IUPAC Name:formonitrile
Traditional IUPAC Name:hydrogen cyanide
SMILES:C#N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitriles. These are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassOrganic cyanides
Direct ParentNitriles
Alternative Parents
Substituents
  • Carbonitrile
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:0
Melting point:-13.4 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000 mg/mL at 25 deg CPhysProp
LogP:-0.25PhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.26 g/LALOGPS
logP-0.65ALOGPS
logP-0.35ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity7.01 m³·mol⁻¹ChemAxon
Polarizability2.31 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Thiosulfate Disproportionation IIIPW002060 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
  • thiosulfate disproportionation III (rhodanese) PWY-5350
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-74b665f5c9189546344aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-4292bd1fdf6103a76243View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-4292bd1fdf6103a76243View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-4292bd1fdf6103a76243View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-e4243e331f99da46857aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e4243e331f99da46857aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-e4243e331f99da46857aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-9000000000-ff23e89c9d09e6b92cbcView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18407
HMDB IDHMDB0060292
Pubchem Compound ID768
Kegg IDC01326
ChemSpider ID748
WikipediaHydrogen_cyanide
BioCyc IDHCN
EcoCyc IDHCN
Ligand ExpoCYN

Enzymes

General function:
Involved in thiosulfate sulfurtransferase activity
Specific function:
Catalyzes, although with low efficiency, the sulfur transfer reaction from thiosulfate to cyanide. The relatively low affinity of glpE for both thiosulfate and cyanide suggests that these compounds are not the physiological substrates. Thioredoxin 1 or related dithiol proteins could instead be the physiological sulfur-acceptor substrate. Possible association with the metabolism of glycerol-phosphate remains to be elucidated
Gene Name:
glpE
Uniprot ID:
P0A6V5
Molecular weight:
12082
Reactions
Thiosulfate + cyanide = sulfite + thiocyanate.
General function:
Involved in thiosulfate sulfurtransferase activity
Specific function:
Transfers a sulfur ion to cyanide or to other thiol compounds. Also has weak rhodanese activity (130-fold lower). Its participation in detoxification of cyanide may be small. May be involved in the enhancement of serine sensitivity
Gene Name:
sseA
Uniprot ID:
P31142
Molecular weight:
30812
Reactions
3-mercaptopyruvate + cyanide = pyruvate + thiocyanate.
General function:
Involved in thiosulfate sulfurtransferase activity
Specific function:
Thiosulfate + cyanide = sulfite + thiocyanate
Gene Name:
ynjE
Uniprot ID:
P78067
Molecular weight:
48228
Reactions
Thiosulfate + cyanide = sulfite + thiocyanate.
General function:
Inorganic ion transport and metabolism
Specific function:
The phage shock protein (psp) operon (pspABCDE) may play a significant role in the competition for survival under nutrient- or energy-limited conditions. PspE catalyzes the sulfur-transfer reaction from thiosulfate to cyanide, to form sulfite and thiocyanate. Also able to use dithiol (dithiothreitol) as an alternate sulfur acceptor. Also possesses a very low mercaptopyruvate sulfurtransferase activity
Gene Name:
pspE
Uniprot ID:
P23857
Molecular weight:
11475
Reactions
Thiosulfate + cyanide = sulfite + thiocyanate.

Transporters

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 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