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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:10:54 UTC
Update Date2023-02-21 17:17:52 UTC
HMDB IDHMDB0012974
Secondary Accession Numbers
  • HMDB12974
Metabolite Identification
Common NameHypothiocyanite
DescriptionAs 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
Data?1676999872
Synonyms
ValueSource
(Hydroxysulfanyl)formonitrileChEBI
Cyanosulfoxylic acidChEBI
Hypocyanous acidChEBI
(Hydroxysulphanyl)formonitrileGenerator
CyanosulfoxylateGenerator
CyanosulphoxylateGenerator
Cyanosulphoxylic acidGenerator
N,6-didehydro-3,6-dihydro-3-Methyl-adenosineHMDB
OSCN-hypothiocyanite ionHMDB
Hypothiocyanite ionMeSH, HMDB
HypothiocyaniteChEBI
Chemical FormulaCHNOS
Average Molecular Weight75.09
Monoisotopic Molecular Weight74.977884349
IUPAC Name(hydroxysulfanyl)formonitrile
Traditional Namecyanosulfoxylic acid
CAS Registry Number63296-34-4
SMILES
OSC#N
InChI Identifier
InChI=1S/CHNOS/c2-1-4-3/h3H
InChI KeyZCZCOXLLICTZAH-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).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiocyanates
Sub ClassNot Available
Direct ParentThiocyanates
Alternative Parents
Substituents
  • Sulfenyl compound
  • So-thioperoxol
  • Thiocyanate
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility48.2 g/LALOGPS
logP-0.93ALOGPS
logP0.35ChemAxon
logS-0.19ALOGPS
pKa (Strongest Acidic)11.97ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity17.01 m³·mol⁻¹ChemAxon
Polarizability5.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+111.53131661259
DarkChem[M-H]-102.93731661259
DeepCCS[M+H]+121.02830932474
DeepCCS[M-H]-119.24330932474
DeepCCS[M-2H]-154.54630932474
DeepCCS[M+Na]+128.18930932474
AllCCS[M+H]+124.232859911
AllCCS[M+H-H2O]+119.932859911
AllCCS[M+NH4]+128.332859911
AllCCS[M+Na]+129.532859911
AllCCS[M-H]-145.632859911
AllCCS[M+Na-2H]-152.532859911
AllCCS[M+HCOO]-159.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HypothiocyaniteOSC#N1456.0Standard polar33892256
HypothiocyaniteOSC#N835.8Standard non polar33892256
HypothiocyaniteOSC#N897.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hypothiocyanite,1TMS,isomer #1C[Si](C)(C)OSC#N935.0Semi standard non polar33892256
Hypothiocyanite,1TMS,isomer #1C[Si](C)(C)OSC#N954.2Standard non polar33892256
Hypothiocyanite,1TMS,isomer #1C[Si](C)(C)OSC#N1573.7Standard polar33892256
Hypothiocyanite,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OSC#N1174.0Semi standard non polar33892256
Hypothiocyanite,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OSC#N1196.1Standard non polar33892256
Hypothiocyanite,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OSC#N1701.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hypothiocyanite GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9000000000-cbb88d0f0c22744d614a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hypothiocyanite GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hypothiocyanite GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 10V, Positive-QTOFsplash10-004i-9000000000-f7a7bcf898c44fd7a75d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 20V, Positive-QTOFsplash10-004i-9000000000-12711117650ea75273122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 40V, Positive-QTOFsplash10-004i-9000000000-023113a0379555c516902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 10V, Negative-QTOFsplash10-00fr-9000000000-e6b998396d2c5773b4452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 20V, Negative-QTOFsplash10-00fr-9000000000-b35bd047c03698b19d5c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 40V, Negative-QTOFsplash10-00di-9000000000-ed0388cc4e8680d3e19f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 10V, Positive-QTOFsplash10-004i-9000000000-131cb52af4ee79a0ed7f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 20V, Positive-QTOFsplash10-004i-9000000000-131cb52af4ee79a0ed7f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 40V, Positive-QTOFsplash10-0002-9000000000-e010d396dd95ce012f8d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 10V, Negative-QTOFsplash10-00di-9000000000-b1d947606d8698ba4a8b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 20V, Negative-QTOFsplash10-00di-9000000000-b1d947606d8698ba4a8b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hypothiocyanite 40V, Negative-QTOFsplash10-00di-9000000000-b1d947606d8698ba4a8b2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029228
KNApSAcK IDNot Available
Chemspider ID111270
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHypothiocyanite
METLIN IDNot Available
PubChem Compound124985
PDB IDNot Available
ChEBI ID133907
Food Biomarker OntologyNot Available
VMH IDCE2011
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:
TPO
Uniprot ID:
P07202
Molecular weight:
102961.63
General function:
Involved in peroxidase activity
Specific function:
May contribute to airway host defense against infection.
Gene Name:
LPO
Uniprot ID:
P22079
Molecular weight:
70983.6
General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715
General function:
Involved in 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
General function:
Involved in catalytic activity
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHB
Uniprot ID:
P21953
Molecular weight:
43122.065
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHA
Uniprot ID:
P12694
Molecular weight:
50470.58