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Showing metabocard for Cyanosulfurous acid anion (HMDB0012916)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:09:48 UTC
Update Date2020-02-26 21:37:57 UTC
HMDB IDHMDB0012916
Secondary Accession Numbers
  • HMDB12916
Metabolite Identification
Common NameCyanosulfurous acid anion
DescriptionThe OSCN- ion inhibits bacterial glyceraldehyde 3-P dehydrogenases (11, 24) and. thereby stops the bacterial production of acids from sugars. The inhibition of bacterial acid production by OSCN- has been implicated as playing an important role in the prevention of dental caries. Lactoperoxidase in the presence of thiocyanate detoxifies hydrogen peroxide by converting it into OSCN-, and OSCN- prevents bacteria from excreting hydrogen peroxide by inhibiting glyceraldehyde 3-P dehydrogenase. Because of this inhibition, no NADH is generated in the bacteria, and the hydrogen peroxide-producing NADH oxidases become short of their substrate, NADH. This inhibition of glycolysis usually has a bacteriostatic effect. In recent studies, significant levels of OSCN- have been found in saliva collected directly from the ducts of the salivary glands. This indicates that hydrogen peroxide is actually produced within the salivary glands; thus, lactoperoxidase and thiocyanate may also play an important role in protecting the salivary glands and ducts against hydrogen peroxide toxicity. The products of the lactoperoxidase-thiocyanate-hydrogen peroxide reaction have also been reported to be bactericidal. This effect has been ascribed to OSCN-, but it has also been suggested that higher oxyacids of the thiocyanate ion, cyanosulfurous and cyanosulfuric acids, may be formed in the lactoperoxidase reaction, and these acids may be the effective molecular species in the. killing.
Structure
Data?1582753077
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012916 (Cyanosulfurous acid anion)


  Mrv1652303102016472D          

  5  4  0  0  0  0            999 V2000
   12.4281  -13.2962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2531  -13.2962    0.0000 S   0  0  0  0  0  3  0  0  0  0  0  0
   13.6656  -14.0107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6656  -12.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0781  -11.8673    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
  2  4  1  0  0  0  0
  4  5  3  0  0  0  0
M  END
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3D MOL for HMDB0012916 (Cyanosulfurous acid anion)

HMDB0012916
     RDKit          3D
Cyanosulfurous acid anion
  7  6  0  0  0  0  0  0  0  0999 V2000
    2.5650   -0.6033    0.3246 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -0.4057   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0586   -0.0796   -0.7067 S   0  0  0  0  0  3  0  0  0  0  0  0
   -1.1211   -1.2336   -0.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5513    1.4703   -0.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8868   -0.8127    0.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4632    1.6646    0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  4  6  1  0
  5  7  1  0
M  RAD  1   3   2
M  END
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3D SDF for HMDB0012916 (Cyanosulfurous acid anion)


  Mrv1652303102016472D          

  5  4  0  0  0  0            999 V2000
   12.4281  -13.2962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2531  -13.2962    0.0000 S   0  0  0  0  0  3  0  0  0  0  0  0
   13.6656  -14.0107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6656  -12.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0781  -11.8673    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
  2  4  1  0  0  0  0
  4  5  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012916

> <DATABASE_NAME>
hmdb

> <SMILES>
O[S](O)C#N

> <INCHI_IDENTIFIER>
InChI=1S/CH2NO2S/c2-1-5(3)4/h3-4H

> <INCHI_KEY>
QYFNKYSGTDITHU-UHFFFAOYSA-N

> <FORMULA>
CH2NO2S

> <MOLECULAR_WEIGHT>
92.097

> <EXACT_MASS>
91.980624003

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
7.012236731281856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
dihydroxy-lambda3-sulfanecarbonitrile

> <ALOGPS_LOGP>
-0.52

> <JCHEM_LOGP>
-0.5677999999999999

> <ALOGPS_LOGS>
-0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.31625246233585

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207679910402014

> <JCHEM_PKA_STRONGEST_BASIC>
-3.888490287086733

> <JCHEM_POLAR_SURFACE_AREA>
64.25

> <JCHEM_REFRACTIVITY>
17.5406

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.62e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydroxy-lambda3-sulfanecarbonitrile

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0012916 (Cyanosulfurous acid anion)

HMDB0012916
     RDKit          3D
Cyanosulfurous acid anion
  7  6  0  0  0  0  0  0  0  0999 V2000
    2.5650   -0.6033    0.3246 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -0.4057   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0586   -0.0796   -0.7067 S   0  0  0  0  0  3  0  0  0  0  0  0
   -1.1211   -1.2336   -0.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5513    1.4703   -0.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8868   -0.8127    0.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4632    1.6646    0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  4  6  1  0
  5  7  1  0
M  RAD  1   3   2
M  END
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PDB for HMDB0012916 (Cyanosulfurous acid anion)

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      23.199 -24.820   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0      24.739 -24.820   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      25.509 -26.153   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      25.509 -23.486   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      26.279 -22.152   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0012916 (Cyanosulfurous acid anion)

COMPND    HMDB0012916
HETATM    1  N1  UNL     1       2.565  -0.603   0.325  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.516  -0.406  -0.084  1.00  0.00           C  
HETATM    3  S1  UNL     1      -0.059  -0.080  -0.707  1.00  0.00           S  
HETATM    4  O1  UNL     1      -1.121  -1.234  -0.103  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.551   1.470  -0.388  1.00  0.00           O  
HETATM    6  H1  UNL     1      -1.887  -0.813   0.369  1.00  0.00           H  
HETATM    7  H2  UNL     1      -0.463   1.665   0.589  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    5
CONECT    4    6
CONECT    5    7
END
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SMILES for HMDB0012916 (Cyanosulfurous acid anion)

O[S](O)C#N
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INCHI for HMDB0012916 (Cyanosulfurous acid anion)

InChI=1S/CH2NO2S/c2-1-5(3)4/h3-4H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Cyanosulphurous acid anionGenerator
CNSuHMDB
Cyanosulfurous acidHMDB
Dihydroxy-λ⁴-sulphanylGenerator
Chemical FormulaCH2NO2S
Average Molecular Weight92.097
Monoisotopic Molecular Weight91.980624003
IUPAC Namedihydroxy-lambda3-sulfanecarbonitrile
Traditional Namedihydroxy-lambda3-sulfanecarbonitrile
CAS Registry NumberNot Available
SMILES
O[S](O)C#N
InChI Identifier
InChI=1S/CH2NO2S/c2-1-5(3)4/h3-4H
InChI KeyQYFNKYSGTDITHU-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
  • 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
Source
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 Solubility26.2 g/LALOGPS
logP-0.52ALOGPS
logP-0.57ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.25 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity17.54 m³·mol⁻¹ChemAxon
Polarizability7.01 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]+115.16931661259
DarkChem[M-H]-110.69731661259
DeepCCS[M+H]+117.30230932474
DeepCCS[M-H]-115.40730932474
DeepCCS[M-2H]-150.64930932474
DeepCCS[M+Na]+124.91430932474
AllCCS[M+H]+124.632859911
AllCCS[M+H-H2O]+120.332859911
AllCCS[M+NH4]+128.632859911
AllCCS[M+Na]+129.732859911
AllCCS[M-H]-133.432859911
AllCCS[M+Na-2H]-139.032859911
AllCCS[M+HCOO]-145.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 20228.3171 minutes33406817
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid319.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid508.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid356.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid109.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid277.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid141.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid249.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid258.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)730.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid544.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid49.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid589.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid223.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid329.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate647.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA382.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water318.4 seconds40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cyanosulfurous acid anion,1TMS,isomer #1C[Si](C)(C)O[SH](O)C#N1065.3Semi standard non polar33892256
Cyanosulfurous acid anion,1TMS,isomer #1C[Si](C)(C)O[SH](O)C#N1277.5Standard non polar33892256
Cyanosulfurous acid anion,1TMS,isomer #1C[Si](C)(C)O[SH](O)C#N2091.6Standard polar33892256
Cyanosulfurous acid anion,2TMS,isomer #1C[Si](C)(C)O[SH](C#N)O[Si](C)(C)C1157.3Semi standard non polar33892256
Cyanosulfurous acid anion,2TMS,isomer #1C[Si](C)(C)O[SH](C#N)O[Si](C)(C)C1451.1Standard non polar33892256
Cyanosulfurous acid anion,2TMS,isomer #1C[Si](C)(C)O[SH](C#N)O[Si](C)(C)C1388.9Standard polar33892256
Cyanosulfurous acid anion,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[SH](O)C#N1306.1Semi standard non polar33892256
Cyanosulfurous acid anion,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[SH](O)C#N1607.5Standard non polar33892256
Cyanosulfurous acid anion,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[SH](O)C#N2159.4Standard polar33892256
Cyanosulfurous acid anion,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[SH](C#N)O[Si](C)(C)C(C)(C)C1564.0Semi standard non polar33892256
Cyanosulfurous acid anion,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[SH](C#N)O[Si](C)(C)C(C)(C)C1996.1Standard non polar33892256
Cyanosulfurous acid anion,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[SH](C#N)O[Si](C)(C)C(C)(C)C1607.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cyanosulfurous acid anion GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-e74b498f9c4ecccdaddd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyanosulfurous acid anion 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 - Cyanosulfurous acid anion 10V, Positive-QTOFsplash10-0006-9000000000-0a5a6919ee3b0e9e9db42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanosulfurous acid anion 20V, Positive-QTOFsplash10-004l-9000000000-414a0e948c6c3f3f54b62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanosulfurous acid anion 40V, Positive-QTOFsplash10-004l-9000000000-d1e0360a1ad70f1968032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanosulfurous acid anion 10V, Negative-QTOFsplash10-0006-9000000000-ba4a83da0125cc3283272017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanosulfurous acid anion 20V, Negative-QTOFsplash10-03fu-9000000000-05f61601cad53c78239b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanosulfurous acid anion 40V, Negative-QTOFsplash10-03di-9000000000-398cf0b390d62bce989b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanosulfurous acid anion 10V, Positive-QTOFsplash10-00fr-9000000000-53a464959c4f8e4b3b6b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanosulfurous acid anion 20V, Positive-QTOFsplash10-00b9-9000000000-72b23769dfe27a08dd9f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanosulfurous acid anion 40V, Positive-QTOFsplash10-002b-9000000000-ef9035abfef8253114b02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanosulfurous acid anion 10V, Negative-QTOFsplash10-03di-9000000000-27b1e0396a4123b0408f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanosulfurous acid anion 20V, Negative-QTOFsplash10-03di-9000000000-27b1e0396a4123b0408f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyanosulfurous acid anion 40V, Negative-QTOFsplash10-03k9-9000000000-ee5dcc294789772ad47f2021-09-25Wishart 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 IDFDB029207
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE1950
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available