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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-09 19:58:59 UTC

Update Date

2023-02-21 17:30:37 UTC

HMDB ID

HMDB0061934

Secondary Accession Numbers

HMDB61934

Metabolite Identification

Common Name

Thiocarbamic acid

Description

Thiocarbamic 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
Thiocarbamate	Generator

Chemical Formula

CH₃NS₂

Average Molecular Weight

93.171

Monoisotopic Molecular Weight

92.970690481

IUPAC Name

sulfanylmethanimidothioic acid

Traditional Name

sulfanylmethanimidothioic acid

CAS Registry Number

Not Available

SMILES

SC(S)=N

InChI Identifier

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

InChI Key

DKVNPHBNOWQYFE-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.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Organosulfur compounds

Alternative Parents

Substituents

Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0061934)

Source

Exogenous

Exogenous (HMDB: HMDB0061934)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.85 g/L	ALOGPS
logP	0.54	ALOGPS
logP	0.93	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-2.4	ChemAxon
pKa (Strongest Basic)	13.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	23.85 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	34.8 m³·mol⁻¹	ChemAxon
Polarizability	8.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	115.12	31661259
DarkChem	[M-H]-	107.461	31661259
DeepCCS	[M+H]+	122.61	30932474
DeepCCS	[M-H]-	120.738	30932474
DeepCCS	[M-2H]-	156.021	30932474
DeepCCS	[M+Na]+	130.129	30932474
AllCCS	[M+H]+	125.0	32859911
AllCCS	[M+H-H2O]+	120.7	32859911
AllCCS	[M+NH4]+	128.9	32859911
AllCCS	[M+Na]+	130.0	32859911
AllCCS	[M-H]-	148.2	32859911
AllCCS	[M+Na-2H]-	155.1	32859911
AllCCS	[M+HCOO]-	162.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.4426 minutes	33406817
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2124.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	670.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	245.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	520.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	338.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	529.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	733.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	1354.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1147.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	298.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1308.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	465.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	437.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	1058.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	580.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	358.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thiocarbamic acid	SC(S)=N	1552.6	Standard polar	33892256
Thiocarbamic acid	SC(S)=N	937.7	Standard non polar	33892256
Thiocarbamic acid	SC(S)=N	1156.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thiocarbamic acid,1TMS,isomer #1	C[Si](C)(C)SC(=N)S	1178.6	Semi standard non polar	33892256
Thiocarbamic acid,1TMS,isomer #1	C[Si](C)(C)SC(=N)S	1050.0	Standard non polar	33892256
Thiocarbamic acid,1TMS,isomer #1	C[Si](C)(C)SC(=N)S	1822.6	Standard polar	33892256
Thiocarbamic acid,1TMS,isomer #2	C[Si](C)(C)N=C(S)S	1148.9	Semi standard non polar	33892256
Thiocarbamic acid,1TMS,isomer #2	C[Si](C)(C)N=C(S)S	1068.2	Standard non polar	33892256
Thiocarbamic acid,1TMS,isomer #2	C[Si](C)(C)N=C(S)S	1606.6	Standard polar	33892256
Thiocarbamic acid,2TMS,isomer #1	C[Si](C)(C)SC(=N)S[Si](C)(C)C	1365.4	Semi standard non polar	33892256
Thiocarbamic acid,2TMS,isomer #1	C[Si](C)(C)SC(=N)S[Si](C)(C)C	1297.1	Standard non polar	33892256
Thiocarbamic acid,2TMS,isomer #1	C[Si](C)(C)SC(=N)S[Si](C)(C)C	1747.5	Standard polar	33892256
Thiocarbamic acid,2TMS,isomer #2	C[Si](C)(C)N=C(S)S[Si](C)(C)C	1342.7	Semi standard non polar	33892256
Thiocarbamic acid,2TMS,isomer #2	C[Si](C)(C)N=C(S)S[Si](C)(C)C	1170.3	Standard non polar	33892256
Thiocarbamic acid,2TMS,isomer #2	C[Si](C)(C)N=C(S)S[Si](C)(C)C	1544.1	Standard polar	33892256
Thiocarbamic acid,3TMS,isomer #1	C[Si](C)(C)N=C(S[Si](C)(C)C)S[Si](C)(C)C	1463.3	Semi standard non polar	33892256
Thiocarbamic acid,3TMS,isomer #1	C[Si](C)(C)N=C(S[Si](C)(C)C)S[Si](C)(C)C	1258.4	Standard non polar	33892256
Thiocarbamic acid,3TMS,isomer #1	C[Si](C)(C)N=C(S[Si](C)(C)C)S[Si](C)(C)C	1459.5	Standard polar	33892256
Thiocarbamic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC(=N)S	1400.4	Semi standard non polar	33892256
Thiocarbamic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC(=N)S	1321.1	Standard non polar	33892256
Thiocarbamic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC(=N)S	2002.4	Standard polar	33892256
Thiocarbamic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(S)S	1376.7	Semi standard non polar	33892256
Thiocarbamic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(S)S	1298.0	Standard non polar	33892256
Thiocarbamic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(S)S	1819.4	Standard polar	33892256
Thiocarbamic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC(=N)S[Si](C)(C)C(C)(C)C	1830.2	Semi standard non polar	33892256
Thiocarbamic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC(=N)S[Si](C)(C)C(C)(C)C	1802.8	Standard non polar	33892256
Thiocarbamic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)SC(=N)S[Si](C)(C)C(C)(C)C	1812.2	Standard polar	33892256
Thiocarbamic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(S)S[Si](C)(C)C(C)(C)C	1802.4	Semi standard non polar	33892256
Thiocarbamic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(S)S[Si](C)(C)C(C)(C)C	1650.6	Standard non polar	33892256
Thiocarbamic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(S)S[Si](C)(C)C(C)(C)C	1815.9	Standard polar	33892256
Thiocarbamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(S[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2123.9	Semi standard non polar	33892256
Thiocarbamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(S[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	1892.5	Standard non polar	33892256
Thiocarbamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(S[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	1850.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Thiocarbamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-716a4b1d56d805d4cdbc	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiocarbamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 10V, Positive-QTOF	splash10-0006-9000000000-a15dea2f948c88019289	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 20V, Positive-QTOF	splash10-0006-9000000000-42ee588c0bdc0ace8c02	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 40V, Positive-QTOF	splash10-056r-9000000000-722a6085cb177789f5f0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 10V, Negative-QTOF	splash10-0a4i-9000000000-25206fb5f5f12bd47cc7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 20V, Negative-QTOF	splash10-0a4i-9000000000-e6593581fa895f380ca3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-1b9661016717b0dc8eb9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 10V, Positive-QTOF	splash10-0a4i-9000000000-64a97e187d151b5e24c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 20V, Positive-QTOF	splash10-0a4i-9000000000-0773b54bff34bba4eae3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-a0c600644500a24a5946	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 10V, Negative-QTOF	splash10-0a4i-9000000000-286b63d3516de7d14a12	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 20V, Negative-QTOF	splash10-0a4i-9000000000-286b63d3516de7d14a12	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiocarbamic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-286b63d3516de7d14a12	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thiocarbamate

METLIN ID

Not Available

PubChem Compound

3001860

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
McElhinney RS: Derivatives of thiocarbamic acid. I. Preparation of 4-substituted thiosemicarbazides. J Chem Soc Perkin 1. 1966;10:950-5. [PubMed:5948935 ]
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 ]
LIEBERMEISTER K: [Bacteriostatic properties of thiocarbamic acid derivatives]. Zentralbl Bakteriol Orig. 1950 Jul 15;155(8):403-9. [PubMed:14782663 ]
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 ]
Hans Millauer, Gerhard Edelmann, 'Process for the preparation of thiocarbamic acid O-esters.' U.S. Patent US3963768, issued January, 1967. [Link]
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]
Paolo Koch, Bartolomeo Anfossi, 'Method for synthesizing thiocarbamic acid esters.' U.S. Patent US4020093, issued April 26, 1977. [Link]
Villiam Giroldini, Carlo Neri, 'Synthesizing thiocarbamic acid esters.' U.S. Patent US4497739, issued May, 1973. [Link]

Showing metabocard for Thiocarbamic acid (HMDB0061934)

MOL for HMDB0061934 (Thiocarbamic acid)

3D MOL for HMDB0061934 (Thiocarbamic acid)

3D SDF for HMDB0061934 (Thiocarbamic acid)

3D-SDF for HMDB0061934 (Thiocarbamic acid)

PDB for HMDB0061934 (Thiocarbamic acid)

3D PDB for HMDB0061934 (Thiocarbamic acid)

SMILES for HMDB0061934 (Thiocarbamic acid)

INCHI for HMDB0061934 (Thiocarbamic acid)

Structure for HMDB0061934 (Thiocarbamic acid)

3D Structure for HMDB0061934 (Thiocarbamic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra