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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-09 21:16:27 UTC
Update Date2020-03-27 16:04:06 UTC
HMDB IDHMDB0060292
Secondary Accession Numbers
  • HMDB60292
Metabolite Identification
Common NameHydrogen cyanide
DescriptionHydrogen cyanide, also known as cyanide or HCN, belongs to the class of organic compounds known as nitriles. Nitriles are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N. Hydrogen cyanide is a very weakly acidic compound (based on its pKa). Hydrogen cyanide exists in all living organisms, ranging from bacteria to humans. Hydrogen cyanide is a bitter tasting compound. Outside of the human body, Hydrogen cyanide has been detected, but not quantified in, several different foods, such as oil-seed camellia, amaranths, common thymes, summer grapes, and mung beans. This could make hydrogen cyanide a potential biomarker for the consumption of these foods. Hydrogen cyanide is weakly acidic with a pKa of 9.2. Hydrogen cyanide is a potentially toxic compound. Hydrogen cyanide is a linear molecule, with a triple bond between carbon and nitrogen. Oxygen therapy can also be administered. Skin contact with cyanide salts can irritate and produce sores.
Structure
Data?1563866039
Synonyms
ValueSource
[CHN]ChEBI
BlausaeureChEBI
CyanwasserstoffChEBI
FormonitrileChEBI
HCNChEBI
Hydrocyanic acidChEBI
CyanideKegg
HydrocyanateGenerator
Zyklon bHMDB
Cyanide, hydrogenHMDB
Acid, hydrocyanicHMDB
Chemical FormulaCHN
Average Molecular Weight27.0253
Monoisotopic Molecular Weight27.010899037
IUPAC Nameformonitrile
Traditional Namehydrogen cyanide
CAS Registry Number74-90-8
SMILES
C#N
InChI Identifier
InChI=1S/CHN/c1-2/h1H
InChI KeyLELOWRISYMNNSU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitriles. Nitriles 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
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Role

Environmental role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-74b665f5c9189546344aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-4292bd1fdf6103a76243Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-4292bd1fdf6103a76243Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-4292bd1fdf6103a76243Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-e4243e331f99da46857aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e4243e331f99da46857aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-e4243e331f99da46857aSpectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9000000000-ff23e89c9d09e6b92cbcSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030908
KNApSAcK IDC00007569
Chemspider IDNot Available
KEGG Compound IDC01326
BioCyc IDHCN
BiGG IDNot Available
Wikipedia LinkHydrogen_cyanide
METLIN IDNot Available
PubChem Compound768
PDB IDNot Available
ChEBI ID18407
Food Biomarker OntologyNot Available
VMH IDCYAN
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Enzymes

General function:
Involved in thiosulfate sulfurtransferase activity
Specific function:
Transfer of a sulfur ion to cyanide or to other thiol compounds. Also has weak rhodanese activity. May have a role in cyanide degradation or in thiosulfate biosynthesis.
Gene Name:
MPST
Uniprot ID:
P25325
Molecular weight:
33178.15
Reactions
3-Mercaptopyruvic acid + Hydrogen cyanide → Pyruvic acid + Thiocyanatedetails
Thiosulfate + Hydrogen cyanide → Sulfite + Thiocyanatedetails
General function:
Involved in thiosulfate sulfurtransferase activity
Specific function:
Formation of iron-sulfur complexes, cyanide detoxification or modification of sulfur-containing enzymes. Other thiol compounds, besides cyanide, can act as sulfur ion acceptors. Also has weak mercaptopyruvate sulfurtransferase (MST) activity (By similarity). Together with MRPL18, acts as a mitochondrial import factor for the cytosolic 5S rRNA. Only the nascent unfolded cytoplasmic form is able to bind to the 5S rRNA.
Gene Name:
TST
Uniprot ID:
Q16762
Molecular weight:
33428.69
Reactions
Thiosulfate + Hydrogen cyanide → Sulfite + Thiocyanatedetails
Hydrogen cyanide + 3-Mercaptopyruvic acid → Thiocyanate + Pyruvic aciddetails