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Showing metabocard for Thioacetamide (HMDB0258996)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 20:53:26 UTC
Update Date2022-11-23 22:29:20 UTC
HMDB IDHMDB0258996
Secondary Accession NumbersNone
Metabolite Identification
Common NameThioacetamide
Descriptionthioacetamide, also known as acetothioamide or TAA, belongs to the class of organic compounds known as thioamides. These are organic compounds containing the functional group with the general structure R-CS-NR'R, where R, R', and R are organic groups. Based on a literature review a significant number of articles have been published on thioacetamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Thioacetamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Thioacetamide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0258996 (Thioacetamide)


  Mrv1572004191601072D          

  4  3  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 N   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  1  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
M  END
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3D MOL for HMDB0258996 (Thioacetamide)

HMDB0258996
     RDKit          3D
THIOACETAMIDE
  9  8  0  0  0  0  0  0  0  0999 V2000
   -0.9832   -0.3789   -0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587    0.2537   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463    1.4381    0.3914 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186   -0.5866   -0.7346 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.3958    0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2148   -0.6531   -1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884   -1.2586    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2797    1.9476    0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4608   -1.1581    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  2  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  3  8  1  0
  4  9  1  0
M  END
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3D SDF for HMDB0258996 (Thioacetamide)


  Mrv1572004191601072D          

  4  3  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 N   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  1  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258996

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(S)=N

> <INCHI_IDENTIFIER>
InChI=1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4)

> <INCHI_KEY>
YUKQRDCYNOVPGJ-UHFFFAOYSA-N

> <FORMULA>
C2H5NS

> <MOLECULAR_WEIGHT>
75.13

> <EXACT_MASS>
75.014270339

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
7.7004989056003

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethanimidothioic acid

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
-0.05564122652911933

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3285836400588455

> <JCHEM_PKA_STRONGEST_BASIC>
12.171222064838476

> <JCHEM_POLAR_SURFACE_AREA>
23.85

> <JCHEM_REFRACTIVITY>
31.529500000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thioacetamide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0258996 (Thioacetamide)

HMDB0258996
     RDKit          3D
THIOACETAMIDE
  9  8  0  0  0  0  0  0  0  0999 V2000
   -0.9832   -0.3789   -0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587    0.2537   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463    1.4381    0.3914 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186   -0.5866   -0.7346 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.3958    0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2148   -0.6531   -1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884   -1.2586    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2797    1.9476    0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4608   -1.1581    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  2  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  3  8  1  0
  4  9  1  0
M  END
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PDB for HMDB0258996 (Thioacetamide)

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.310  -1.334   0.000  0.00  0.00           N+0
HETATM    4  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0258996 (Thioacetamide)

COMPND    HMDB0258996
HETATM    1  C1  UNL     1      -0.983  -0.379  -0.149  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.359   0.254  -0.103  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.546   1.438   0.391  1.00  0.00           N  
HETATM    4  S1  UNL     1       1.819  -0.587  -0.735  1.00  0.00           S  
HETATM    5  H1  UNL     1      -1.718   0.396   0.137  1.00  0.00           H  
HETATM    6  H2  UNL     1      -1.215  -0.653  -1.199  1.00  0.00           H  
HETATM    7  H3  UNL     1      -0.988  -1.259   0.525  1.00  0.00           H  
HETATM    8  H4  UNL     1      -0.280   1.948   0.764  1.00  0.00           H  
HETATM    9  H5  UNL     1       2.461  -1.158   0.369  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    3    4
CONECT    3    8
CONECT    4    9
END
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SMILES for HMDB0258996 (Thioacetamide)

CC(S)=N
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INCHI for HMDB0258996 (Thioacetamide)

InChI=1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Acetic acid thioamideChEBI
AcetothioamideChEBI
MethylthioamideChEBI
TAAChEBI
ThiacetamideChEBI
Thioacetimidic acidChEBI
ThioactamideChEBI
Acetate thioamideGenerator
ThioacetimidateGenerator
ThioacetamideMeSH
ThioacetamidMeSH
ThiacetamidMeSH
Chemical FormulaC2H5NS
Average Molecular Weight75.13
Monoisotopic Molecular Weight75.014270339
IUPAC Nameethanimidothioic acid
Traditional Namethioacetamide
CAS Registry NumberNot Available
SMILES
CC(S)=N
InChI Identifier
InChI=1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4)
InChI KeyYUKQRDCYNOVPGJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thioamides. These are organic compounds containing the functional group with the general structure R-CS-NR'R, where R, R', and R are organic groups.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThioamides
Sub ClassNot Available
Direct ParentThioamides
Alternative Parents
Substituents
  • Thioamide
  • Thiocarboxylic acid amide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Thiocarbonyl group
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
PropertyValueSource
logP0.66ALOGPS
logP-0.056ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)12.17ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area23.85 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.53 m³·mol⁻¹ChemAxon
Polarizability7.7 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+122.20730932474
DeepCCS[M-H]-120.31130932474
DeepCCS[M-2H]-155.67930932474
DeepCCS[M+Na]+129.81130932474
AllCCS[M+H]+122.532859911
AllCCS[M+H-H2O]+118.132859911
AllCCS[M+NH4]+126.732859911
AllCCS[M+Na]+127.932859911
AllCCS[M-H]-148.532859911
AllCCS[M+Na-2H]-155.332859911
AllCCS[M+HCOO]-162.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202211.8214 minutes33406817
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1425.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid483.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid171.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid355.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid160.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid379.5 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 Acid498.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)670.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid869.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid223.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1040.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid336.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid323.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate689.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA429.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water225.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
THIOACETAMIDECC(S)=N1155.4Standard polar33892256
THIOACETAMIDECC(S)=N725.4Standard non polar33892256
THIOACETAMIDECC(S)=N866.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
THIOACETAMIDE,1TMS,isomer #1CC(=N)S[Si](C)(C)C966.0Semi standard non polar33892256
THIOACETAMIDE,1TMS,isomer #1CC(=N)S[Si](C)(C)C943.2Standard non polar33892256
THIOACETAMIDE,1TMS,isomer #1CC(=N)S[Si](C)(C)C1483.2Standard polar33892256
THIOACETAMIDE,1TMS,isomer #2CC(S)=N[Si](C)(C)C929.5Semi standard non polar33892256
THIOACETAMIDE,1TMS,isomer #2CC(S)=N[Si](C)(C)C905.2Standard non polar33892256
THIOACETAMIDE,1TMS,isomer #2CC(S)=N[Si](C)(C)C1259.5Standard polar33892256
THIOACETAMIDE,2TMS,isomer #1CC(=N[Si](C)(C)C)S[Si](C)(C)C1140.0Semi standard non polar33892256
THIOACETAMIDE,2TMS,isomer #1CC(=N[Si](C)(C)C)S[Si](C)(C)C1009.7Standard non polar33892256
THIOACETAMIDE,2TMS,isomer #1CC(=N[Si](C)(C)C)S[Si](C)(C)C1199.5Standard polar33892256
THIOACETAMIDE,1TBDMS,isomer #1CC(=N)S[Si](C)(C)C(C)(C)C1193.4Semi standard non polar33892256
THIOACETAMIDE,1TBDMS,isomer #1CC(=N)S[Si](C)(C)C(C)(C)C1204.7Standard non polar33892256
THIOACETAMIDE,1TBDMS,isomer #1CC(=N)S[Si](C)(C)C(C)(C)C1545.1Standard polar33892256
THIOACETAMIDE,1TBDMS,isomer #2CC(S)=N[Si](C)(C)C(C)(C)C1155.1Semi standard non polar33892256
THIOACETAMIDE,1TBDMS,isomer #2CC(S)=N[Si](C)(C)C(C)(C)C1122.3Standard non polar33892256
THIOACETAMIDE,1TBDMS,isomer #2CC(S)=N[Si](C)(C)C(C)(C)C1462.8Standard polar33892256
THIOACETAMIDE,2TBDMS,isomer #1CC(=N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C1578.0Semi standard non polar33892256
THIOACETAMIDE,2TBDMS,isomer #1CC(=N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C1477.9Standard non polar33892256
THIOACETAMIDE,2TBDMS,isomer #1CC(=N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C1458.1Standard polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal 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 ID2006126
KEGG Compound IDC19302
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThioacetamide
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID32497
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]