Cyanate (ECMDB02078) (M2MDB000437)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)Transporters (5)XML
Proteins (70)
Record Information
Version2.0
Creation Date2012-05-31 13:55:28 -0600
Update Date2015-09-17 15:41:13 -0600
Secondary Accession Numbers
  • ECMDB02078
Identification
Name:Cyanate
DescriptionThe cyanate ion is an anion consisting of one oxygen atom, one carbon atom, and one nitrogen atom, [OCN], in that order. The cyanate ion possesses 1 unit of negative charge, borne mainly by the nitrogen atom. In organic compounds the cyanate group is a functional group.; The cyanate ion is an ambident nucleophile in nucleophilic substitution because it can react to form an alkyl cyanate R-OCN (exception) or an alkyl isocyanate R-NCO (rule). Aryl cyanates (C6H5OCN) can be formed by a reaction of phenol with cyanogen chloride (ClCN) in the presence of a base. The cyanate ion is relatively non-toxic in comparison with cyanides. Use of this fact is made in cyanide decontamination processes where a permanganate oxidation converts toxic cyanide to safer cyanate. Cyanate can be decomposed by the enzyme cyanate lyase (or cyanase), which is found in bacteria and plants. In particular cyanate can be decomposed to carbamate (ammonia) and carbon dioxide. Alternately the same enzyme can be used to synthesize cyanate using carbamate and carbon dioxide.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Cyanic acid
  • Hydrogen cyanate
  • Hydrogen cyanic acid
Chemical Formula:CNO
Weight:Average: 42.0168
Monoisotopic: 41.997988627
InChI Key:XLJMAIOERFSOGZ-UHFFFAOYSA-M
InChI:InChI=1S/CHNO/c2-1-3/h3H/p-1
CAS number:71000-82-3
IUPAC Name:cyanic acid
Traditional IUPAC Name:cyanic acid
SMILES:[O-]C#N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyanates. These are organic compounds containing the cyanate functional group with the formula [OCN]-.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxoanionic compounds
Sub ClassCyanates
Direct ParentCyanates
Alternative Parents
Substituents
  • Organic cyanate
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility15.5 g/LALOGPS
logP-1.1ALOGPS
logP-0.54ChemAxon
logS-0.44ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity9.22 m³·mol⁻¹ChemAxon
Polarizability3.16 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Cyanate + 3 Hydrogen ion + Hydrogen carbonate >2 Carbon dioxide + Ammonium
Cyanate + Hydrogen ion + Hydrogen carbonate <> Carbon dioxide + Carbamic acid
Cyanate + Hydrogen carbonate + Hydrogen ion > Carbamic acid + Carbon dioxide
Cyanate + Carbonic acid + 2 Hydrogen ion > Ammonia +2 Carbon dioxide
Cyanate + Hydrogen carbonate + 2 Hydrogen ion + Carbamic acid <> Ammonia +2 Carbon dioxide
Hydrogen carbonate + Cyanate + Hydrogen ion + Cyanate > Carbamic acid
Cyanate + Hydrogen ion + Hydrogen carbonate <> Carbon dioxide + Carbamic acid
Cyanate + Hydrogen ion + Hydrogen carbonate <> Carbon dioxide + Carbamic acid
SMPDB Pathways:
Nitrogen metabolismPW000755 ThumbThumb?image type=greyscaleThumb?image type=simple
cyanate degradationPW002099 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, Positive (Annotated)splash10-0006-9000000000-5051e8304fc346b1051cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-af39beb571105afa6347View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-866a3d8943d2093ad754View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-5f0d8b45c37b6532d33cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-5f0d8b45c37b6532d33cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5f0d8b45c37b6532d33cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-005e171faa9586cdda44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-005e171faa9586cdda44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-005e171faa9586cdda44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-fd9f25340762315b4515View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-fd9f25340762315b4515View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-fd9f25340762315b4515View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299View 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Hseu, Tzong Hsiung; Lan, Shih Li; Yang, Min Der. Cyanate from alkaline hydrolysis of cyanogen bromide-activated polysaccharides. Analytical Biochemistry (1981), 116(1), 181-4.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID29195
HMDB IDHMDB02078
Pubchem Compound ID540
Kegg IDC01417
ChemSpider ID94771
WikipediaCyanate
BioCyc IDCPD-69
EcoCyc IDCPD-69

Enzymes

Protein Details
1. Cyanate hydratase
General function:
Involved in cyanate hydratase activity
Specific function:
Catalyzes the reaction of cyanate with bicarbonate to produce ammonia and carbon dioxide
Gene Name:
cynS
Uniprot ID:
P00816
Molecular weight:
17049
Reactions
Cyanate + HCO(3)(-) + 2 H(+) = NH(3) + 2 CO(2).

Transporters

Protein Details
1. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
2. Outer membrane pore protein E
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
Protein Details
3. Outer membrane protein F
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
Protein Details
4. Cyanate transport protein cynX
General function:
Involved in transporter activity
Specific function:
This protein is part of an active transport system that transports exogenous cyanate into E.coli cells
Gene Name:
cynX
Uniprot ID:
P17583
Molecular weight:
41360
Protein Details
5. Outer membrane protein C
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