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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:14 -0600
Update Date	2015-09-17 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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x6a02f3cc> Close
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:	cyanosulfanide
Traditional IUPAC Name:	thiocyanate
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).
Kingdom	Organic compounds
Super Class	Organosulfur compounds
Class	Thiocyanates
Sub Class	Not Available
Direct Parent	Thiocyanates
Alternative Parents	Organopnictogen compounds Organonitrogen compounds Hydrocarbon derivatives Organic anions
Substituents	Thiocyanate Organic nitrogen compound Organopnictogen compound Hydrocarbon derivative Organonitrogen compound Organic anion Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	pseudohalide anion (CHEBI:18022 ) sulfur molecular entity (CHEBI:18022 ) a perthiol (HSCN )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 41.5 g/L ALOGPS logP 0.22 ALOGPS logP 0.51 ChemAxon logS -0.26 ALOGPS pKa (Strongest Acidic) 0.5 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 23.79 Ų ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 16.09 m³·mol⁻¹ ChemAxon Polarizability 4.75 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Hydrogen cyanide + Thiosulfate > Hydrogen ion + Sulfite + Thiocyanate Hydrogen cyanide + 3-Mercaptopyruvic acid + Cyanide <> Hydrogen ion + Pyruvic acid + Thiocyanate Thiosulfate + Cyanide <> Sulfite + Thiocyanate Hydrogen cyanide + 3-Mercaptopyruvic acid <> Thiocyanate + Pyruvic acid Hydrogen cyanide + 3-Mercaptopyruvic acid Hydrogen ion + Pyruvic acid + Thiocyanate <i>S</i>-sulfanyl-[acceptor] + Hydrogen cyanide an unsulfurated sulfur acceptor + Thiocyanate + Hydrogen ion Thiosulfate + Hydrogen cyanide > Sulfite + Thiocyanate 3-Mercaptopyruvic acid + Hydrogen cyanide > Pyruvic acid + Thiocyanate Cyanide + Thiosulfate + Cyanide + Thiosulfate > Thiocyanate + Sulfite + Hydrogen ion + Thiocyanate + Sulfite Hydrogen cyanide + Thiosulfate > Thiocyanate + Sulfite +2 Hydrogen ion Thiosulfate + Cyanide <> Sulfite + Thiocyanate Thiosulfate + Cyanide <> Sulfite + Thiocyanate
SMPDB Pathways:	Sulfur metabolism PW000922 Thiosulfate Disproportionation III PW002060 sulfur metabolism (butanesulfonate) PW000923 sulfur metabolism (ethanesulfonate) PW000925 sulfur metabolism (isethionate) PW000926 sulfur metabolism (methanesulfonate) PW000927 sulfur metabolism (propanesulfonate) PW000924
KEGG Pathways:	Cysteine and methionine metabolism ec00270 Metabolic pathways eco01100 Microbial metabolism in diverse environments ec01120 Sulfur metabolism ec00920
EcoCyc Pathways:	thiosulfate disproportionation III (rhodanese) PWY-5350
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) splash10-0a4i-9000000000-afccae6819a2082a3b0e View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) splash10-0a4i-9000000000-f7f42d61861dc8b47e0a View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) splash10-0a4i-9000000000-d0c4694dff8128c82e83 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4i-9000000000-96a5deef504fc8cb3052 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4i-9000000000-3714ea8b8485698022fe View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9000000000-a4aa9bc6ab8c5ca45d18 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4l-9000000000-3e068a4808fd5db992f0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-052f-9000000000-5b443ccd8993bc2f9325 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-052f-9000000000-626420c56c66b85a0f64 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4i-9000000000-286b63d3516de7d14a12 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a4i-9000000000-286b63d3516de7d14a12 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-286b63d3516de7d14a12 View 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)
Links
External Links:	Resource Link CHEBI ID 18022 HMDB ID HMDB01453 Pubchem Compound ID 781 Kegg ID C01755 ChemSpider ID 760 Wikipedia Thiocyanate BioCyc ID HSCN EcoCyc ID HSCN Ligand Expo SCN

Enzymes

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