Canmetcon
Record Information
Version2.0
Creation Date2012-07-30 14:55:14 -0600
Update Date2015-09-17 15:41:11 -0600
Secondary Accession Numbers
  • ECMDB21289
Identification
Name:Thiocyanate
Description:Thiocyanate is analogous to the cyanate ion, [OCN]-, wherein oxygen is replaced by sulfur. [SCN]- is one of the pseudohalogens, due to the similarity of its reactions to that of halide ions. Thiocyanate was formerly known as rhodanide (from a Greek word for rose) because of the red color of its complexes with iron. Thiocyanates are typically colorless. Cyanide ions can react with cystine to yield thicocyanate. This reaction occurs to a slight extent even in neutral solution, but is more pronounced in alkaline solutions of cystine. In addition to this non-enzymatic route, cyanide produced in vivo can be converted in part to thiocyanate by sulfur transferase systems. The thiocyanate ion can be oxidized at acid pH by hydrogen peroxide to generate sulfate and cyanide. The reaction is catalyzed by hemoglobin acting as a peroxidase; Thiocyanate is analogous to the cyanate ion, [OCN]-, wherein oxygen is replaced by sulfur. [SCN]- is one of the pseudohalides, due to the similarity of its reactions to that of halide ions. Thiocyanate used to be known as rhodanide (from a Greek word for rose) because of the red colour of its complexes with iron. Thiocyanate is produced by the reaction of elemental sulfur or thiosulfate with cyanide:; Thiocyanate shares its negative charge approximately equally between sulfur and nitrogen. As a consequence, thiocyanate can act as a nucleophile at either sulfur or nitrogen
Structure
Thumb
Synonyms:
  • Allyl isothiocyanate
  • Allyl isothiocyanic acid
  • Ammonium rhodanate
  • Ammonium rhodanic acid
  • Ammonium rhodanide
  • Ammonium sulfocyanate
  • Ammonium sulfocyanic acid
  • Ammonium sulphocyanate
  • Ammonium sulphocyanic acid
  • HSCN
  • Hydrogen thiocyanate
  • Hydrogen thiocyanic acid
  • N3C1S
  • NCS-
  • Nitridosulfanidocarbon
  • Nitridosulfidocarbonate(1)
  • Nitridosulfidocarbonic acid(1)
  • Nitridosulphanidocarbon
  • Nitridosulphidocarbonate(1)
  • Nitridosulphidocarbonic acid(1)
  • Nitridothiocarbonate(1)
  • Nitridothiocarbonate(4)
  • Nitridothiocarbonic acid(1)
  • Nitridothiocarbonic acid(4)
  • Rhodanid
  • Rhodanide
  • SCN
  • Silver thiocyanate agscn
  • Silver thiocyanic acid agscn
  • Thallium thiocyanate
  • Thallium thiocyanic acid
  • Thiocyanate
  • Thiocyanate ion
  • Thiocyanate ion (1)
  • Thiocyanic acid
  • Thiocyanic acid ion
  • Thiocyanic acid ion (1)
  • Thiocyanid
  • Thiozyanat
  • Weedazol TL
  • [S1C3N]
Chemical Formula:CNS
Weight:Average: 58.082
Monoisotopic: 57.975144695
InChI Key:ZMZDMBWJUHKJPS-UHFFFAOYSA-M
InChI:InChI=1S/CHNS/c2-1-3/h3H/p-1
CAS number:Not Available
IUPAC Name:sulfanylformonitrile
Traditional IUPAC Name:thiocyanate ion
SMILES:[S-]C#N
Chemical Taxonomy
Description belongs to the class of organic compounds known as thiocyanates. These are salts or esters of thiocyanic acid, with the general formula RSC#N (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiocyanates
Sub ClassNot Available
Direct ParentThiocyanates
Alternative Parents
Substituents
  • Thiocyanate
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic anion
  • 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 Solubility6.75 g/LALOGPS
logP0.32ALOGPS
logP0.51ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)0.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity15.35 m³·mol⁻¹ChemAxon
Polarizability5.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Sulfur metabolismPW000922 ThumbThumb?image type=greyscaleThumb?image type=simple
Thiosulfate Disproportionation IIIPW002060 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (butanesulfonate)PW000923 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (ethanesulfonate)PW000925 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (isethionate)PW000926 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (methanesulfonate)PW000927 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (propanesulfonate)PW000924 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • thiosulfate disproportionation III (rhodanese) PWY-5350
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9000000000-afccae6819a2082a3b0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9000000000-f7f42d61861dc8b47e0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-9000000000-d0c4694dff8128c82e83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-96a5deef504fc8cb3052View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-3714ea8b8485698022feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a4aa9bc6ab8c5ca45d18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-9000000000-3e068a4808fd5db992f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9000000000-5b443ccd8993bc2f9325View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-626420c56c66b85a0f64View in MoNA
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
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID18022
HMDB IDHMDB01453
Pubchem Compound ID781
Kegg IDC01755
ChemSpider ID760
WikipediaThiocyanate
BioCyc IDHSCN
EcoCyc IDHSCN
Ligand ExpoSCN

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