Thiocyanate
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Basic Info
| Common Name | Thiocyanate(F03340) |
| 2D Structure | |
| Description | Thiocyanates are a group of compounds formed from a combination of sulfur, carbon, and nitrogen. Thiocyanates are found in various foods and plants and are produced primarily from the reaction of free cyanide with sulfur. This reaction occurs in the environment (for example, in industrial waste streams that contain cyanide) and in the human body after cyanide ingestion. Thiocyanates are present in water primarily because of discharges from coal processing, extraction of gold and silver, and mining industries. Thiocyanate is the major product formed from cyanide that passes into the body as the body attempts to rid itself of cyanide. (L191) |
| FRCD ID | F03340 |
| CAS Number | 302-04-5 |
| PubChem CID | 781 |
| Formula | CHNS |
| IUPAC Name | thiocyanic acid |
| InChI Key | ZMZDMBWJUHKJPS-UHFFFAOYSA-N |
| InChI | InChI=1S/CHNS/c2-1-3/h3H |
| Canonical SMILES | C(#N)S |
| Isomeric SMILES | C(#N)S |
| Wikipedia | Thiocyanate |
| Synonyms |
UNII-A5KWW7N91V
CHEBI:29200
thiocyanic acid
463-56-9
HSCN
nitridosulfanidocarbon
HS-C#N
N#C-SH
A5KWW7N91V
[CN(SH)]
|
| Classifies |
Plant Toxin
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organosulfur compounds |
| Class | Thiocyanates |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Thiocyanates |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Thiocyanate - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aliphatic acyclic compound |
| 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). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 59.086 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 31.3 |
| Monoisotopic Mass | 58.983 |
| Exact Mass | 58.983 |
| XLogP | 0.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 3 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Konzo: a distinct neurological disease associated with food (cassava) cyanogenic poisoning. | Brain Res Bull | 2018 Jul 5 | 29981837 |
| Cyanate improves insulin sensitivity and hepatic steatosis in normal and high fat-fed mice: Anorexic and antioxidative effects. | Chem Biol Interact | 2018 Jan 5 | 29113807 |
| Exploring anaerobic environments for cyanide and cyano-derivatives microbial degradation. | Appl Microbiol Biotechnol | 2018 Feb | 29209795 |
| Dietary cyanogen exposure and early child neurodevelopment: An observational study from the Democratic Republic of Congo. | PLoS One | 2018 | 29664942 |
| Cyanide and the human brain: perspectives from a model of food (cassava) poisoning. | Ann N Y Acad Sci | 2016 Aug | 27450775 |
| Detection of thiocyanate through limiting growth of AuNPs with C-dots acting asreductant. | Analyst | 2015 Nov 21 | 26421502 |
| Ultrasensitive turn-on fluorescent detection of trace thiocyanate based onfluorescence resonance energy transfer. | Talanta | 2015 Jan | 25476353 |
| In vitro metabolic conversion of the organic breakdown products of glucosinolate to goitrogenic thiocyanate anion. | J Sci Food Agric | 2015 Aug 30 | 25271103 |
| Correlation of Serum Thyroid Hormones Autoantibodies with Self-Reported Exposure to Thyroid Disruptors in a Group of Nonsegmental Vitiligo Patients. | Arch Environ Contam Toxicol | 2015 Aug | 25700983 |
| Disorder in milk proteins: structure, functional disorder, and biocidalpotentials of lactoperoxidase. | Curr Protein Pept Sci | 2015 | 25772156 |
| Biochemical, oxidative and histological changes caused by sub-acute oral exposure of some synthetic cyanogens in rats: ameliorative effect of α-ketoglutarate. | Food Chem Toxicol | 2014 May | 24632070 |
| Reactions of (+)-catechin with salivary nitrite and thiocyanate under conditions simulating the gastric lumen: production of dinitrosocatechin and its thiocyanate conjugate. | Free Radic Res | 2014 Aug | 24886172 |
| Acute toxicity of some synthetic cyanogens in rats: time-dependent cyanide generation and cytochrome oxidase inhibition in soft tissues after sub-lethal oral intoxication. | Food Chem Toxicol | 2013 Sep | 23831730 |
| Enhancement of iron(II)-dependent reduction of nitrite to nitric oxide by thiocyanate and accumulation of iron(II)/thiocyanate/nitric oxide complex under conditions simulating the mixture of saliva and gastric juice. | Chem Res Toxicol | 2012 Jan 13 | 22145785 |
| Effects of the food additive sulfite on nitrite-dependent nitric oxide productionunder conditions simulating the mixture of saliva and gastric juice. | J Agric Food Chem | 2012 Feb 1 | 22224438 |
| Decreased mucosal sulfide detoxification is related to an impaired butyrate oxidation in ulcerative colitis. | Inflamm Bowel Dis | 2012 Dec | 22434643 |
| Konzo and continuing cyanide intoxication from cassava in Mozambique. | Food Chem Toxicol | 2011 Mar | 20654676 |
| Appearance of konzo in South-Kivu, a wartorn area in the Democratic Republic of Congo. | Food Chem Toxicol | 2011 Mar | 20691241 |
| Exploiting the bead injection LOV approach to carry out spectrophotometric assaysin wine: application to the determination of iron. | Talanta | 2011 Jun 15 | 21641441 |
| Acute toxicity of some synthetic cyanogens in rats and their response to oral treatment with alpha-ketoglutarate. | Food Chem Toxicol | 2009 Sep | 19539683 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
- Gene Name:
- CA1
- Uniprot ID:
- P00915
- Molecular Weight:
- 28870.0 Da
- Mechanism of Action:
- Thiocyanates also act as inhibitors to carbonic anhydrase, which catalyzes the rapid conversion of carbon dioxide to bicarbonate and protons.
References
- Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA3
- Uniprot ID:
- P07451
- Molecular Weight:
- 29557.215 Da
- Mechanism of Action:
- Thiocyanates also act as inhibitors to carbonic anhydrase, which catalyzes the rapid conversion of carbon dioxide to bicarbonate and protons.
References
- Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
- Gene Name:
- CA4
- Uniprot ID:
- P22748
- Molecular Weight:
- 35032.075 Da
- Mechanism of Action:
- Thiocyanates also act as inhibitors to carbonic anhydrase, which catalyzes the rapid conversion of carbon dioxide to bicarbonate and protons.
References
- Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
- General Function:
- Peroxidase activity
- Specific Function:
- Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis.
- Gene Name:
- EPX
- Uniprot ID:
- P11678
- Molecular Weight:
- 81039.5 Da
- Mechanism of Action:
- Thiocyanate is known to modulate activity of mammalian peroxidases, such as eosinophil peroxidase has been implicated in promoting oxidative tissue damage in a variety of in ammatory conditions, including asthma. It uses H2O2 to oxidize chloride, bromide and thiocyanate to their respective hypohalous acids.
References
- van Dalen CJ, Kettle AJ: Substrates and products of eosinophil peroxidase. Biochem J. 2001 Aug 15;358(Pt 1):233-9. [11485572 ]
- General Function:
- Sodium:iodide symporter activity
- Specific Function:
- Mediates iodide uptake in the thyroid gland.
- Gene Name:
- SLC5A5
- Uniprot ID:
- Q92911
- Molecular Weight:
- 68665.63 Da
- Mechanism of Action:
- Thiocyanate is a competitive inhibitor of the human thyroid sodium/iodide symporter NIS, which plays an important role in moving thiocyanate ions into epithelial cells.
References
- Laurberg P, Nohr SB, Pedersen KM, Fuglsang E: Iodine nutrition in breast-fed infants is impaired by maternal smoking. J Clin Endocrinol Metab. 2004 Jan;89(1):181-7. [14715847 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
- Gene Name:
- CA2
- Uniprot ID:
- P00918
- Molecular Weight:
- 29245.895 Da
- Mechanism of Action:
- Thiocyanates also act as inhibitors to carbonic anhydrase, which catalyzes the rapid conversion of carbon dioxide to bicarbonate and protons.
References
- Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
- General Function:
- Thiocyanate peroxidase activity
- Specific Function:
- Antimicrobial agent which utilizes hydrogen peroxide and thiocyanate (SCN) to generate the antimicrobial substance hypothiocyanous acid (HOSCN) (By similarity). May contribute to airway host defense against infection.
- Gene Name:
- LPO
- Uniprot ID:
- P22079
- Molecular Weight:
- 80287.055 Da
- Mechanism of Action:
- The LPO enzyme catalyzes the peroxidation of thiocyanate in the presence of H2O2. In order for the reaction to occur, the SCN– ion must bind to LPO at the substrate-binding site in the distal heme cavity with a favorable orientation.
References
- Sheikh IA, Singh AK, Singh N, Sinha M, Singh SB, Bhushan A, Kaur P, Srinivasan A, Sharma S, Singh TP: Structural evidence of substrate specificity in mammalian peroxidases: structure of the thiocyanate complex with lactoperoxidase and its interactions at 2.4 A resolution. J Biol Chem. 2009 May 29;284(22):14849-56. doi: 10.1074/jbc.M807644200. Epub 2009 Apr 1. [19339248 ]
- General Function:
- Peroxidase activity
- Specific Function:
- Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
- Gene Name:
- MPO
- Uniprot ID:
- P05164
- Molecular Weight:
- 83867.71 Da
- Mechanism of Action:
- Myeloperoxidase is considered to oxidize thiocyanate to hypothiocyanite either directly or via initial formation of thiocyanogen which rapidly hydrolyses to hypothiocyanite.
References
- van Dalen CJ, Whitehouse MW, Winterbourn CC, Kettle AJ: Thiocyanate and chloride as competing substrates for myeloperoxidase. Biochem J. 1997 Oct 15;327 ( Pt 2):487-92. [9359420 ]