Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2009-07-25 00:10:54 UTC |
---|
Update Date | 2023-02-21 17:17:52 UTC |
---|
HMDB ID | HMDB0012974 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Hypothiocyanite |
---|
Description | As it is an organic compound, hypothiocyanite occurs naturally in the antimicrobial immune system of the human respiratory tract in a redox reaction catalyzed by the enzyme lactoperoxidase. It has been researched extensively for its capabilities as an alternative antibiotic as it is harmless to human body cells while being cytotoxic to bacteria. Of late, the exact processes for making hypothiocyanite have been patented as such an effective antimicrobial has many commercial applications. Whether or not this antimicrobial compound comprises the entirety of the immune system of the respiratory tract remains to be seen. Hypothiocyanite is the anion [OSCN]- and the conjugate base of hypothiocyanous acid. It is an organic compound part of the thiocyanates as it contains the functional group SCN. It is formed when an oxygen is singly bonded to the thiocyanate group. Hypothiocyanous acid (HOSCN) is a fairly weak acid as its acid dissociation constant is 5.3. |
---|
Structure | InChI=1S/CHNOS/c2-1-4-3/h3H |
---|
Synonyms | Value | Source |
---|
(Hydroxysulfanyl)formonitrile | ChEBI | Cyanosulfoxylic acid | ChEBI | Hypocyanous acid | ChEBI | (Hydroxysulphanyl)formonitrile | Generator | Cyanosulfoxylate | Generator | Cyanosulphoxylate | Generator | Cyanosulphoxylic acid | Generator | N,6-didehydro-3,6-dihydro-3-Methyl-adenosine | HMDB | OSCN-hypothiocyanite ion | HMDB | Hypothiocyanite ion | MeSH, HMDB | Hypothiocyanite | ChEBI |
|
---|
Chemical Formula | CHNOS |
---|
Average Molecular Weight | 75.09 |
---|
Monoisotopic Molecular Weight | 74.977884349 |
---|
IUPAC Name | (hydroxysulfanyl)formonitrile |
---|
Traditional Name | cyanosulfoxylic acid |
---|
CAS Registry Number | 63296-34-4 |
---|
SMILES | OSC#N |
---|
InChI Identifier | InChI=1S/CHNOS/c2-1-4-3/h3H |
---|
InChI Key | ZCZCOXLLICTZAH-UHFFFAOYSA-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 | |
---|
Substituents | - Sulfenyl compound
- So-thioperoxol
- Thiocyanate
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
---|
Hypothiocyanite | OSC#N | 1456.0 | Standard polar | 33892256 | Hypothiocyanite | OSC#N | 835.8 | Standard non polar | 33892256 | Hypothiocyanite | OSC#N | 897.6 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Hypothiocyanite,1TMS,isomer #1 | C[Si](C)(C)OSC#N | 935.0 | Semi standard non polar | 33892256 | Hypothiocyanite,1TMS,isomer #1 | C[Si](C)(C)OSC#N | 954.2 | Standard non polar | 33892256 | Hypothiocyanite,1TMS,isomer #1 | C[Si](C)(C)OSC#N | 1573.7 | Standard polar | 33892256 | Hypothiocyanite,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OSC#N | 1174.0 | Semi standard non polar | 33892256 | Hypothiocyanite,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OSC#N | 1196.1 | Standard non polar | 33892256 | Hypothiocyanite,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OSC#N | 1701.7 | Standard polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Hypothiocyanite GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9000000000-cbb88d0f0c22744d614a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hypothiocyanite GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hypothiocyanite GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 10V, Positive-QTOF | splash10-004i-9000000000-f7a7bcf898c44fd7a75d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 20V, Positive-QTOF | splash10-004i-9000000000-12711117650ea7527312 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 40V, Positive-QTOF | splash10-004i-9000000000-023113a0379555c51690 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 10V, Negative-QTOF | splash10-00fr-9000000000-e6b998396d2c5773b445 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 20V, Negative-QTOF | splash10-00fr-9000000000-b35bd047c03698b19d5c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 40V, Negative-QTOF | splash10-00di-9000000000-ed0388cc4e8680d3e19f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 10V, Positive-QTOF | splash10-004i-9000000000-131cb52af4ee79a0ed7f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 20V, Positive-QTOF | splash10-004i-9000000000-131cb52af4ee79a0ed7f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 40V, Positive-QTOF | splash10-0002-9000000000-e010d396dd95ce012f8d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 10V, Negative-QTOF | splash10-00di-9000000000-b1d947606d8698ba4a8b | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 20V, Negative-QTOF | splash10-00di-9000000000-b1d947606d8698ba4a8b | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hypothiocyanite 40V, Negative-QTOF | splash10-00di-9000000000-b1d947606d8698ba4a8b | 2021-09-25 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
|
---|
General References | - Lemma K, Ashby MT: Reactive sulfur species: kinetics and mechanism of the reaction of hypothiocyanous acid with cyanide to give dicyanosulfide in aqueous solution. Chem Res Toxicol. 2009 Sep;22(9):1622-8. doi: 10.1021/tx900212r. [PubMed:19705807 ]
- Kalmar J, Woldegiorgis KL, Biri B, Ashby MT: Mechanism of decomposition of the human defense factor hypothiocyanite near physiological pH. J Am Chem Soc. 2011 Dec 14;133(49):19911-21. doi: 10.1021/ja2083152. Epub 2011 Nov 18. [PubMed:22031955 ]
- Barrett TJ, Hawkins CL: Hypothiocyanous acid: benign or deadly? Chem Res Toxicol. 2012 Feb 20;25(2):263-73. doi: 10.1021/tx200219s. Epub 2011 Nov 21. [PubMed:22053976 ]
- Cegolon L, Salata C, Piccoli E, Juarez V, Palu' G, Mastrangelo G, Calistri A: In vitro antiviral activity of hypothiocyanite against A/H1N1/2009 pandemic influenza virus. Int J Hyg Environ Health. 2014 Jan;217(1):17-22. doi: 10.1016/j.ijheh.2013.03.001. Epub 2013 Mar 14. [PubMed:23540488 ]
- Talib J, Kwan J, Suryo Rahmanto A, Witting PK, Davies MJ: The smoking-associated oxidant hypothiocyanous acid induces endothelial nitric oxide synthase dysfunction. Biochem J. 2014 Jan 1;457(1):89-97. doi: 10.1042/BJ20131135. [PubMed:24112082 ]
- Lloyd MM, Grima MA, Rayner BS, Hadfield KA, Davies MJ, Hawkins CL: Comparative reactivity of the myeloperoxidase-derived oxidants hypochlorous acid and hypothiocyanous acid with human coronary artery endothelial cells. Free Radic Biol Med. 2013 Dec;65:1352-62. doi: 10.1016/j.freeradbiomed.2013.10.007. Epub 2013 Oct 10. [PubMed:24120969 ]
- Rayner BS, Love DT, Hawkins CL: Comparative reactivity of myeloperoxidase-derived oxidants with mammalian cells. Free Radic Biol Med. 2014 Jun;71:240-55. doi: 10.1016/j.freeradbiomed.2014.03.004. Epub 2014 Mar 13. [PubMed:24632382 ]
- Seidel A, Parker H, Turner R, Dickerhof N, Khalilova IS, Wilbanks SM, Kettle AJ, Jameson GN: Uric acid and thiocyanate as competing substrates of lactoperoxidase. J Biol Chem. 2014 Aug 8;289(32):21937-49. doi: 10.1074/jbc.M113.544957. Epub 2014 Jun 13. [PubMed:24928513 ]
- Bonifay V, Barrett TJ, Pattison DI, Davies MJ, Hawkins CL, Ashby MT: Tryptophan oxidation in proteins exposed to thiocyanate-derived oxidants. Arch Biochem Biophys. 2014 Dec 15;564:1-11. doi: 10.1016/j.abb.2014.08.014. Epub 2014 Aug 27. [PubMed:25172223 ]
- Bafort F, Parisi O, Perraudin JP, Jijakli MH: Mode of action of lactoperoxidase as related to its antimicrobial activity: a review. Enzyme Res. 2014;2014:517164. doi: 10.1155/2014/517164. Epub 2014 Sep 16. [PubMed:25309750 ]
- Fabrini R, Bocedi A, Camerini S, Fusetti M, Ottaviani F, Passali FM, Topazio D, Iavarone F, Francia I, Castagnola M, Ricci G: Inactivation of human salivary glutathione transferase P1-1 by hypothiocyanite: a post-translational control system in search of a role. PLoS One. 2014 Nov 13;9(11):e112797. doi: 10.1371/journal.pone.0112797. eCollection 2014. [PubMed:25393952 ]
- Gingerich A, Pang L, Hanson J, Dlugolenski D, Streich R, Lafontaine ER, Nagy T, Tripp RA, Rada B: Hypothiocyanite produced by human and rat respiratory epithelial cells inactivates extracellular H1N2 influenza A virus. Inflamm Res. 2016 Jan;65(1):71-80. doi: 10.1007/s00011-015-0892-z. Epub 2015 Nov 25. [PubMed:26608498 ]
- Cook NL, Moeke CH, Fantoni LI, Pattison DI, Davies MJ: The myeloperoxidase-derived oxidant hypothiocyanous acid inhibits protein tyrosine phosphatases via oxidation of key cysteine residues. Free Radic Biol Med. 2016 Jan;90:195-205. doi: 10.1016/j.freeradbiomed.2015.11.025. Epub 2015 Nov 23. [PubMed:26616646 ]
- Schlorke D, Flemmig J, Gau J, Furtmuller PG, Obinger C, Arnhold J: New insights into thiocyanate oxidation by human myeloperoxidase. J Inorg Biochem. 2016 Sep;162:117-126. doi: 10.1016/j.jinorgbio.2016.06.019. Epub 2016 Jun 15. [PubMed:27343172 ]
- Suzuki S, Ogawa M, Ohta S, Nunomura S, Nanri Y, Shiraishi H, Mitamura Y, Yoshihara T, Lee JJ, Izuhara K: Induction of Airway Allergic Inflammation by Hypothiocyanite via Epithelial Cells. J Biol Chem. 2016 Dec 30;291(53):27219-27227. doi: 10.1074/jbc.M116.746909. Epub 2016 Nov 18. [PubMed:27864363 ]
|
---|