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Showing metabocard for Thiocarbamic acid (HMDB0061934)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-09 19:58:59 UTC
Update Date2023-02-21 17:30:37 UTC
HMDB IDHMDB0061934
Secondary Accession Numbers
  • HMDB61934
Metabolite Identification
Common NameThiocarbamic acid
DescriptionThiocarbamic acid, also known as thiocarbamate, belongs to the class of organic compounds known as organosulfur compounds. These are organic compounds containing a carbon-sulfur bond. Thiocarbamic acid is a very strong basic compound (based on its pKa). Thiocarbamates are a family of organosulfur compounds. This is generally performed by heating to high temperatures and is an important method for synthesising thiophenols. Dithiocarbamates are related to thiocarbamates by the replacement of O by S. Despite this structural similarity their synthesis and chemistry is quite different. Thiocarbamates can be synthesised by the reaction of water or alcohols upon thiocyanates (Riemschneider thiocarbamate synthesis):RSCN + H2O → RSC(O)NH2RSCN + R'OH → RSC(O)NR'HSimilar reactions are seen between alcohols and thiocarbamoyl chlorides such as dimethylthiocarbamoyl chloride; as well as between thiols and cyanates. R2NH + COS → [R2NH2]+][R2NCOS]−In the Newman-Kwart rearrangement O-thiocarbamates can isomerise to S-thiocarbamates. As the name suggests, they are sulphur analogues of carbamates. Dithiocarbamates and their derivatives are widely used in the vulcanization of rubber. There are two isomeric forms of thiocarbamate esters: O-thiocarbamates, ROC(S)NR2, and S-thiocarbamates, RSC(O)NR2.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061934 (Thiocarbamic acid)

  Mrv0541 10091415592D          

  4  3  0  0  0  0            999 V2000
    0.8251    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376   -0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
M  END
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3D MOL for HMDB0061934 (Thiocarbamic acid)

HMDB0061934
     RDKit          3D
Thiocarbamic acid
  7  6  0  0  0  0  0  0  0  0999 V2000
   -0.5291    1.1387    0.2851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195   -0.0780    0.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3490   -1.3301   -0.1050 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5604   -0.5561    0.6089 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1470    1.8884    0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1511   -0.8100   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4412   -0.2529   -0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  1  5  1  0
  3  6  1  0
  4  7  1  0
M  END
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3D SDF for HMDB0061934 (Thiocarbamic acid)

  Mrv0541 10091415592D          

  4  3  0  0  0  0            999 V2000
    0.8251    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376   -0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061934

> <DATABASE_NAME>
hmdb

> <SMILES>
SC(S)=N

> <INCHI_IDENTIFIER>
InChI=1S/CH3NS2/c2-1(3)4/h(H3,2,3,4)

> <INCHI_KEY>
DKVNPHBNOWQYFE-UHFFFAOYSA-N

> <FORMULA>
CH3NS2

> <MOLECULAR_WEIGHT>
93.171

> <EXACT_MASS>
92.970690481

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
8.607791098812584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
sulfanylmethanimidothioic acid

> <ALOGPS_LOGP>
0.54

> <JCHEM_LOGP>
0.9309340677044315

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.33982834369862

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.37584056330119

> <JCHEM_PKA_STRONGEST_BASIC>
13.697223363933015

> <JCHEM_POLAR_SURFACE_AREA>
23.85

> <JCHEM_REFRACTIVITY>
34.7978

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfanylmethanimidothioic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0061934 (Thiocarbamic acid)

HMDB0061934
     RDKit          3D
Thiocarbamic acid
  7  6  0  0  0  0  0  0  0  0999 V2000
   -0.5291    1.1387    0.2851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195   -0.0780    0.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3490   -1.3301   -0.1050 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5604   -0.5561    0.6089 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1470    1.8884    0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1511   -0.8100   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4412   -0.2529   -0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  1  5  1  0
  3  6  1  0
  4  7  1  0
M  END
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PDB for HMDB0061934 (Thiocarbamic acid)

HEADER    PROTEIN                                 09-OCT-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-OCT-14         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.310   1.334   0.000  0.00  0.00           N+0
HETATM    3  S   UNK     0       2.310  -1.334   0.000  0.00  0.00           S+0
HETATM    4  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0061934 (Thiocarbamic acid)

COMPND    HMDB0061934
HETATM    1  N1  UNL     1      -0.529   1.139   0.285  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.119  -0.078   0.274  1.00  0.00           C  
HETATM    3  S1  UNL     1      -1.349  -1.330  -0.105  1.00  0.00           S  
HETATM    4  S2  UNL     1       1.560  -0.556   0.609  1.00  0.00           S  
HETATM    5  H1  UNL     1       0.147   1.888   0.499  1.00  0.00           H  
HETATM    6  H2  UNL     1      -2.151  -0.810  -1.139  1.00  0.00           H  
HETATM    7  H3  UNL     1       2.441  -0.253  -0.423  1.00  0.00           H  
CONECT    1    2    2    5
CONECT    2    3    4
CONECT    3    6
CONECT    4    7
END
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SMILES for HMDB0061934 (Thiocarbamic acid)

SC(S)=N
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INCHI for HMDB0061934 (Thiocarbamic acid)

InChI=1S/CH3NS2/c2-1(3)4/h(H3,2,3,4)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
ThiocarbamateGenerator
Chemical FormulaCH3NS2
Average Molecular Weight93.171
Monoisotopic Molecular Weight92.970690481
IUPAC Namesulfanylmethanimidothioic acid
Traditional Namesulfanylmethanimidothioic acid
CAS Registry NumberNot Available
SMILES
SC(S)=N
InChI Identifier
InChI=1S/CH3NS2/c2-1(3)4/h(H3,2,3,4)
InChI KeyDKVNPHBNOWQYFE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organosulfur compounds. These are organic compounds containing a carbon-sulfur bond.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassNot Available
Sub ClassNot Available
Direct ParentOrganosulfur compounds
Alternative Parents
Substituents
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThiocarbamate
METLIN IDNot Available
PubChem Compound3001860
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Heikkila RE, Cabbat FS, Cohen G: Inactivation of superoxide dismutase by several thiocarbamic acid derivatives. Experientia. 1978 Dec 15;34(12):1553-4. [PubMed:729714 ]
  2. Anina IA, Medved' IL, Proklina TL: [The gonadotoxic action of pesticides derived from thiocarbamic acid]. Farmakol Toksikol. 1975 Jan-Feb;38(1):90-3. [PubMed:1112403 ]
  3. McElhinney RS: Derivatives of thiocarbamic acid. I. Preparation of 4-substituted thiosemicarbazides. J Chem Soc Perkin 1. 1966;10:950-5. [PubMed:5948935 ]
  4. NATIN I, NOCETTI M, BOCLES J: [Treatment of pulmonary tuberculosis with thiocarbamic hydrazone of ketocholanic acid]. Prensa Med Argent. 1954 Mar 26;41(13):850-2. [PubMed:13166887 ]
  5. LIEBERMEISTER K: [Bacteriostatic properties of thiocarbamic acid derivatives]. Zentralbl Bakteriol Orig. 1950 Jul 15;155(8):403-9. [PubMed:14782663 ]
  6. BARZIZZA CM, RUIZ CL: [Considerations on a tuberculostatic agent, ketocholanic acid thiocarbamic hydrazone]. Prensa Med Argent. 1952 Jul 15;39(29):1644-51. [PubMed:14957737 ]
  7. Hans Millauer, Gerhard Edelmann, 'Process for the preparation of thiocarbamic acid O-esters.' U.S. Patent US3963768, issued January, 1967. [Link]
  8. Venkatachala L. Narayanan, Rudiger D. Haugwitz, '[(1,2,4-Oxadiazol-3-yl)phenyl]carbamic or thiocarbamic acid esters.' U.S. Patent US4003909, issued August, 1966. [Link]
  9. Paolo Koch, Bartolomeo Anfossi, 'Method for synthesizing thiocarbamic acid esters.' U.S. Patent US4020093, issued April 26, 1977. [Link]
  10. Villiam Giroldini, Carlo Neri, 'Synthesizing thiocarbamic acid esters.' U.S. Patent US4497739, issued May, 1973. [Link]