P. aeruginosa Metabolome Database: Thiocyanate (PAMDB001695)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001695

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

🔍MOL SDF PDB SMILES InChI View Structure

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

Average Molecular Weight:

58.082

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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

Substituents

Thiocyanate
Hydrocarbon derivative
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:29200 )
hydracid (CHEBI:29200 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	6.75 mg/mL	ALOGPS
logP	0.32	ALOGPS
logP	0.51	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	0.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	15.35 m³·mol^-1	ChemAxon
Polarizability	5.04 Å³	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
Cyanide + Thiosulfate + Cyanide + Thiosulfate > Thiocyanate + Sulfite + Hydrogen ion + Thiocyanate + Sulfite

Pathways:

Cysteine and methionine metabolism pae00270
Metabolic pathways pae01100
Microbial metabolism in diverse environments pae01120
Sulfur metabolism pae00920

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-4b520f6de4bad9245d97	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-4b520f6de4bad9245d97	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-4b520f6de4bad9245d97	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-83b329eff086a9bf9fc0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-83b329eff086a9bf9fc0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-83b329eff086a9bf9fc0	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

Protein Details

• Thiosulfate sulfurtransferase glpE

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
Locus Tag:: PA0589
Molecular weight:: 12 kDa

Reactions

Thiosulfate + cyanide = sulfite + thiocyanate.

Thiocyanate (PAMDB001695)

Structure for Thiocyanate (PAMDB001695)

Enzymes

Reactions

Transporters