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Showing NP-Card for Thioacetamide (NP0002918)

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Record Information
Version1.0
Created at2020-11-23 19:43:36 UTC
Updated at2021-08-12 19:52:31 UTC
NP-MRD IDNP0002918
Secondary Accession NumbersNone
Natural Product Identification
Common NameThioacetamide
Provided ByBMRBBMRB logo
DescriptionTHIOACETAMIDE, also known as thiacetamide or acetothioamide, 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. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on THIOACETAMIDE (PMID: 20138653) (PMID: 20534638) (PMID: 20931291) (PMID: 21182490).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002918 (Thioacetamide)


     RDKit          2D

  9  8  0  0  0  0  0  0  0  0999 V2000
    1.1578    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1560   -0.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4397    0.1957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1862   -2.0800    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -1.1705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4341    1.4573    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4717    0.8671    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536   -0.5280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095    1.6954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  6
  1  6  1  0
  1  7  1  0
  3  8  1  0
  3  9  1  0
M  END
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3D MOL for NP0002918 (Thioacetamide)

NP0002918
     RDKit          3D

  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.0679   -0.4555   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1389    0.2716    0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2286    1.5151   -0.0144 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4650   -0.5787    1.0017 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8098   -0.9712   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4740   -1.1399    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058    0.2503   -0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0119    2.1192    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4131   -1.0111    0.0357 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 NP0002918 (Thioacetamide)


     RDKit          2D

  9  8  0  0  0  0  0  0  0  0999 V2000
    1.1578    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1560   -0.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4397    0.1957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1862   -2.0800    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -1.1705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4341    1.4573    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4717    0.8671    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536   -0.5280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095    1.6954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  6
  1  6  1  0
  1  7  1  0
  3  8  1  0
  3  9  1  0
M  END
> <DATABASE_ID>
NP0002918

> <DATABASE_NAME>
NP-MRD

> <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 NP0002918 (Thioacetamide)

NP0002918
     RDKit          3D

  9  8  0  0  0  0  0  0  0  0999 V2000
   -1.0679   -0.4555   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1389    0.2716    0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2286    1.5151   -0.0144 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4650   -0.5787    1.0017 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8098   -0.9712   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4740   -1.1399    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058    0.2503   -0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0119    2.1192    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4131   -1.0111    0.0357 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 NP0002918 (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 NP0002918 (Thioacetamide)

COMPND    NP0002918
HETATM    1  C1  UNL     1      -1.068  -0.456  -0.251  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.139   0.272   0.189  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.229   1.515  -0.014  1.00  0.00           N  
HETATM    4  S1  UNL     1       1.465  -0.579   1.002  1.00  0.00           S  
HETATM    5  H1  UNL     1      -0.810  -0.971  -1.202  1.00  0.00           H  
HETATM    6  H2  UNL     1      -1.474  -1.140   0.503  1.00  0.00           H  
HETATM    7  H3  UNL     1      -1.906   0.250  -0.507  1.00  0.00           H  
HETATM    8  H4  UNL     1       1.012   2.119   0.245  1.00  0.00           H  
HETATM    9  H5  UNL     1       2.413  -1.011   0.036  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 NP0002918 (Thioacetamide)

CC(S)=N
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INCHI for NP0002918 (Thioacetamide)

InChI=1S/C2H5NS/c1-2(3)4/h1H3,(H2,3,4)
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View in JSmol
Synonyms
ValueSource
Acetic acid thioamideChEBI
AcetothioamideChEBI
MethylthioamideChEBI
TAAChEBI
ThiacetamideChEBI
Thioacetimidic acidChEBI
ThioactamideChEBI
Acetate thioamideGenerator
ThioacetimidateGenerator
ThioacetamidHMDB
ThiacetamidHMDB
ThioacetamideMeSH
Chemical FormulaC2H5NS
Average Mass75.1300 Da
Monoisotopic Mass75.01427 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
HMDB IDHMDB0258996
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2006126
KEGG Compound IDC19302
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThioacetamide
METLIN IDNot Available
PubChem Compound6117
PDB IDNot Available
ChEBI ID32497
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Mendez M, Mendez-Lopez M, Lopez L, Aller MA, Arias J, Arias JL: Acetylcholinesterase activity in an experimental rat model of Type C hepatic encephalopathy. Acta Histochem. 2011 May;113(3):358-62. doi: 10.1016/j.acthis.2010.01.009. Epub 2010 Feb 7. [PubMed:20138653 ]
  3. Demirel U, Harputluoglu MM, Seckin Y, Ciralik H, Temel I, Ozyalin F, Otlu B, Yilmaz B, Dincturk MS, Aladag H: An antibody of TNF-alpha did not prevent thioacetamide-induced hepatotoxicity in rats. Hum Exp Toxicol. 2011 Jul;30(7):560-6. doi: 10.1177/0960327110374206. Epub 2010 Jun 9. [PubMed:20534638 ]
  4. Gu K, Zhao JD, Ren ZG, Ma NY, Lai ST, Wang J, Liu J, Jiang GL: A natural process of cirrhosis resolution and deceleration of liver regeneration after thioacetamide withdrawal in a rat model. Mol Biol Rep. 2011 Mar;38(3):1687-96. doi: 10.1007/s11033-010-0281-1. Epub 2010 Oct 8. [PubMed:20931291 ]
  5. Avraham Y, Grigoriadis N, Poutahidis T, Vorobiev L, Magen I, Ilan Y, Mechoulam R, Berry E: Cannabidiol improves brain and liver function in a fulminant hepatic failure-induced model of hepatic encephalopathy in mice. Br J Pharmacol. 2011 Apr;162(7):1650-8. doi: 10.1111/j.1476-5381.2010.01179.x. [PubMed:21182490 ]