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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-09-22 19:38:58 UTC
HMDB IDHMDB01453
Secondary Accession NumbersNone
Metabolite Identification
Common NameThiocyanate
DescriptionThiocyanate 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.
Structure
Thumb
Synonyms
  1. Rhodanide
  2. SCN
  3. Ammonium sulfocyanate
  4. HSCN
  5. Hydrogen thiocyanate
  6. Nitridosulfanidocarbon
  7. Rhodanid
  8. Silver thiocyanate agscn
  9. Thallium thiocyanate
  10. Thiocyanate ion
  11. Thiocyanic acid
  12. Thiocyanid
  13. Weedazol TL
Chemical FormulaCNS
Average Molecular Weight58.082
Monoisotopic Molecular Weight57.975144695
IUPAC Namecyanosulfanide
Traditional IUPAC Namethiocyanate
CAS Registry Number302-04-5
SMILES
[S-]C#N
InChI Identifier
InChI=1S/CHNS/c2-1-3/h3H/p-1
InChI KeyZMZDMBWJUHKJPS-UHFFFAOYSA-M
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassThiocyanates
Sub ClassN/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Nitriles
  • a perthiol(Cyc)
  • pseudohalide anion(ChEBI)
  • sulfur molecular entity(ChEBI)
Substituents
  • N/A
Direct ParentThiocyanates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Osmolyte, enzyme cofactor, signalling
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility41.5 g/LALOGPS
logP0.22ALOGPS
logP0.51ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)0.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.79ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.09ChemAxon
Polarizability4.75ChemAxon
Spectra
SpectraMS/MS
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified30.7 +/- 28.8 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified59.8 +/- 26.1 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified4.99 +/- 1.03 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified27.6 (5.2-50.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
SalivaDetected and Quantified661 (293-1029) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.61 (0.0 - 6.58) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.00284 (0.00261-0.00310) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.00273 (0.00247-0.00300) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified32.02 +/- 2.93 uMAdult (>18 years old)Bothuremia details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB013883
KNApSAcK IDNot Available
Chemspider ID8961
KEGG Compound IDC01755
BioCyc IDHSCN
BiGG ID38336
Wikipedia LinkThiocyanate
NuGOwiki LinkHMDB01453
Metagene LinkHMDB01453
METLIN IDNot Available
PubChem Compound9322
PDB IDSCN
ChEBI ID18022
References
Synthesis ReferenceLang, Konrad. Thiocyanate formation in the animal body. II. Biochemische Zeitschrift (1933), 263 262-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Paul BD, Smith ML: Cyanide and thiocyanate in human saliva by gas chromatography-mass spectrometry. J Anal Toxicol. 2006 Oct;30(8):511-5. Pubmed: 17132244

Enzymes

General function:
Involved in thiosulfate sulfurtransferase activity
Specific function:
Transfer of a sulfur ion to cyanide or to other thiol compounds. Also has weak rhodanese activity. May have a role in cyanide degradation or in thiosulfate biosynthesis.
Gene Name:
MPST
Uniprot ID:
P25325
Molecular weight:
33178.15
Reactions
3-Mercaptopyruvic acid + Hydrogen cyanide → Pyruvic acid + Thiocyanatedetails
Thiosulfate + Hydrogen cyanide → Sulfurous acid + Thiocyanatedetails
General function:
Involved in thiosulfate sulfurtransferase activity
Specific function:
Formation of iron-sulfur complexes, cyanide detoxification or modification of sulfur-containing enzymes. Other thiol compounds, besides cyanide, can act as sulfur ion acceptors. Also has weak mercaptopyruvate sulfurtransferase (MST) activity (By similarity). Together with MRPL18, acts as a mitochondrial import factor for the cytosolic 5S rRNA. Only the nascent unfolded cytoplasmic form is able to bind to the 5S rRNA.
Gene Name:
TST
Uniprot ID:
Q16762
Molecular weight:
33428.69
Reactions
Thiosulfate + Hydrogen cyanide → Sulfurous acid + Thiocyanatedetails
Hydrogen cyanide + 3-Mercaptopyruvic acid → Thiocyanate + Pyruvic aciddetails
General function:
Inorganic ion transport and metabolism
Specific function:
Possible role in tumorgenesis
Gene Name:
TSTD1
Uniprot ID:
Q8NFU3
Molecular weight:
12530.1