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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:51 UTC
HMDB IDHMDB0001453
Secondary Accession Numbers
  • HMDB01453
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. Thiocyanate 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. A study shows that thiocyanate has a protective effect in lung in cystic fibrosis, and an anti-inflammatory effect in arterial endothelial cells, a neuronal cell line, and a pancreatic beta cell line (PMID: 19918082 ).
Structure
Thumb
Synonyms
ValueSource
[S-C#N](-)ChEBI
N#C-S(-)ChEBI
RhodanidChEBI
RhodanideChEBI
SCN(-)ChEBI
THIOCYANATE ionChEBI
Thiocyanate ion (1-)ChEBI
ThiozyanatChEBI
Thiocyanic acidGenerator
THIOCYANic acid ionGenerator
Thiocyanic acid ion (1-)Generator
SCNHMDB
Ammonium sulfocyanateHMDB
HSCNHMDB
Hydrogen thiocyanateHMDB
NitridosulfanidocarbonHMDB
Silver thiocyanate agscnHMDB
Thallium thiocyanateHMDB
ThiocyanidHMDB
Weedazol TLHMDB
Thiocyanogen ((SCN)2(1-))MeSH
Thiocyanate ion (2-)MeSH
Chemical FormulaCNS
Average Molecular Weight58.082
Monoisotopic Molecular Weight57.975144695
IUPAC Namecyanosulfanide
Traditional 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
DescriptionThis 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).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiocyanates
Sub ClassNot Available
Direct ParentThiocyanates
Alternative Parents
Substituents
  • Thiocyanate
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Route of exposure:

  Parenteral:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Physiological effect

Health effect:

  Observation:

  Health condition:

    Nervous system disorders:

Role

Indirect biological role:

Biological role:

  Molecular messenger:

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 Area23.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity16.09 m³·mol⁻¹ChemAxon
Polarizability4.75 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9000000000-afccae6819a2082a3b0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9000000000-f7f42d61861dc8b47e0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-9000000000-d0c4694dff8128c82e83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-96a5deef504fc8cb3052View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-3714ea8b8485698022feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a4aa9bc6ab8c5ca45d18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-9000000000-3e068a4808fd5db992f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9000000000-5b443ccd8993bc2f9325View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-626420c56c66b85a0f64View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Beta-mercaptolactate-cysteine disulfiduriaPw000475Pw000475 greyscalePw000475 simpleNot Available
Cysteine MetabolismPw000018Pw000018 greyscalePw000018 simpleMap00270
Cystinosis, ocular nonnephropathicPw000699Pw000699 greyscalePw000699 simpleNot 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
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
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
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Crohn's disease
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
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 ]
  2. Xu Y, Szep S, Lu Z: The antioxidant role of thiocyanate in the pathogenesis of cystic fibrosis and other inflammation-related diseases. Proc Natl Acad Sci U S A. 2009 Dec 1;106(48):20515-9. doi: 10.1073/pnas.0911412106. Epub 2009 Nov 16. [PubMed:19918082 ]

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