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Showing NP-Card for Hypothiocyanite (NP0339133)

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Record Information
Version2.0
Created at2024-09-11 19:50:25 UTC
Updated at2024-09-11 19:50:25 UTC
NP-MRD IDNP0339133
Secondary Accession NumbersNone
Natural Product Identification
Common NameHypothiocyanite
DescriptionHypothiocyanite, also known as cyanosulfoxylate or hypocyanous acid, 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). ; Hypothiocyanite is the anion - and the conjugate base of hypothiocyanous acid. Whether or not this antimicrobial compound comprises the entirety of the immune system of the respiratory tract remains to be seen. Hypothiocyanite is an extremely weak basic (essentially neutral) compound (based on its pKa). Of late, the exact processes for making hypothiocyanite have been patented as such an effective antimicrobial has many commercial applications. 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. Hypothiocyanite was first documented in 2009 (PMID: 19705807). 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 (PMID: 19821602) (PMID: 22031955) (PMID: 23540488) (PMID: 24657078) (PMID: 24928513) (PMID: 25393952).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339133 (Hypothiocyanite)


  Mrv1652303102016472D          

  4  3  0  0  0  0            999 V2000
   11.9610  -14.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7859  -14.1646    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1984  -13.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6109  -12.7356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  3  0  0  0  0
M  END
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3D MOL for NP0339133 (Hypothiocyanite)

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3D SDF for NP0339133 (Hypothiocyanite)

  Mrv1652303102016472D          

  4  3  0  0  0  0            999 V2000
   11.9610  -14.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7859  -14.1646    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1984  -13.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6109  -12.7356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  3  0  0  0  0
M  END
> <DATABASE_ID>
NP0339133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OSC#N

> <INCHI_IDENTIFIER>
InChI=1S/CHNOS/c2-1-4-3/h3H

> <INCHI_KEY>
ZCZCOXLLICTZAH-UHFFFAOYSA-N

> <FORMULA>
CHNOS

> <MOLECULAR_WEIGHT>
75.09

> <EXACT_MASS>
74.977884349

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
5.925577749977944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(hydroxysulfanyl)formonitrile

> <ALOGPS_LOGP>
-0.93

> <JCHEM_LOGP>
0.35457041866666666

> <ALOGPS_LOGS>
-0.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.967349373793665

> <JCHEM_PKA_STRONGEST_BASIC>
-4.12528138390265

> <JCHEM_POLAR_SURFACE_AREA>
44.019999999999996

> <JCHEM_REFRACTIVITY>
17.0137

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.82e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyanosulfoxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339133 (Hypothiocyanite)
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PDB for NP0339133 (Hypothiocyanite)
HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  O   UNK     0      22.327 -26.441   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0      23.867 -26.441   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      24.637 -25.107   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      25.407 -23.773   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END

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3D PDB for NP0339133 (Hypothiocyanite)
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SMILES for NP0339133 (Hypothiocyanite)
OSC#N
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INCHI for NP0339133 (Hypothiocyanite)
InChI=1S/CHNOS/c2-1-4-3/h3H
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View in JSmol
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 ionHMDB
HypothiocyaniteChEBI
Chemical FormulaCHNOS
Average Mass75.0900 Da
Monoisotopic Mass74.97788 Da
IUPAC Name(hydroxysulfanyl)formonitrile
Traditional Namecyanosulfoxylic acid
CAS Registry NumberNot Available
SMILES
OSC#N
InChI Identifier
InChI=1S/CHNOS/c2-1-4-3/h3H
InChI KeyZCZCOXLLICTZAH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0012974  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
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. Nagy P, Jameson GN, Winterbourn CC: Kinetics and mechanisms of the reaction of hypothiocyanous acid with 5-thio-2-nitrobenzoic acid and reduced glutathione. Chem Res Toxicol. 2009 Nov;22(11):1833-40. doi: 10.1021/tx900249d. [PubMed:19821602  ] 
  3. 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  ] 
  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. Flemmig J, Rusch D, Czerwinska ME, Rauwald HW, Arnhold J: Components of a standardised olive leaf dry extract (Ph. Eur.) promote hypothiocyanite production by lactoperoxidase. Arch Biochem Biophys. 2014 May 1;549:17-25. doi: 10.1016/j.abb.2014.03.006. Epub  2014 Mar 18. [PubMed:24657078  ] 
  6. 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  ] 
  7. 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  ]