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Showing metabocard for Thiolutin (HMDB0034228)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:01:54 UTC
Update Date2022-03-07 02:54:02 UTC
HMDB IDHMDB0034228
Secondary Accession Numbers
  • HMDB34228
Metabolite Identification
Common NameThiolutin
DescriptionThiolutin is found in alcoholic beverages. Thiolutin is isolated from several strains of Streptomyces albus and Streptomyces pimprina. Antibiotic which inhibits microbiological growth in beer Some sources erroneously specify "aureothricin" as a synonym of thiolutin. Aureothricin is an antibiotic very similar to Thiolutin, and is created as a by-product during the Thiolutin fermentation. Thiolutin is a sulfur-containing antibiotic, which is a potent inhibitor of bacterial and yeast RNA polymerases. It was found to inhibit in vitro RNA synthesis directed by all three yeast RNA polymerases (I, II, and III). Thiolutin is also an inhibitor of mannan and glucan formation in Saccharomyces cerevisiae and used for the analysis of mRNA stability. Studies have shown that thiolutin inhibits adhesion of human umbilical vein endothelial cells (HUVECs) to vitronectin and thus suppresses tumor cell-induced angiogenesis in vivo
Structure
Data?1563862531
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034228 (Thiolutin)


  Mrv0541 02241216092D          

 14 15  0  0  0  0            999 V2000
   -0.6602    0.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4034   -0.1647    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8988    0.4951    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4034    1.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6602    0.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830    1.1556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776    0.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647   -0.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.9079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2382   -1.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988   -0.6602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4034   -1.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4034    0.5776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    1.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0034228 (Thiolutin)

HMDB0034228
     RDKit          3D
Thiolutin
 22 23  0  0  0  0  0  0  0  0999 V2000
    4.1526    0.4366   -0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7025    0.5776    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926    1.3882    1.1747 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102   -0.1670   -0.3791 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3288   -0.1262   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691    0.6257    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1921    1.8089    1.9131 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729    2.0680    2.4127 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7820    0.9378    1.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562    0.2942    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8229   -0.6513   -0.4815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0087   -1.3005   -1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5677   -0.8958   -0.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2372   -1.7328   -1.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3371    0.0117   -1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531   -0.2983    0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6338    1.4196    0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -0.8326   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8909    0.7660    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4835   -0.5740   -1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193   -2.2256   -1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7277   -1.5302   -0.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13  5  1  0
 10  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  9 19  1  0
 12 20  1  0
 12 21  1  0
 12 22  1  0
M  END
Download

3D SDF for HMDB0034228 (Thiolutin)


  Mrv0541 02241216092D          

 14 15  0  0  0  0            999 V2000
   -0.6602    0.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4034   -0.1647    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8988    0.4951    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4034    1.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6602    0.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830    1.1556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776    0.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647   -0.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.9079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2382   -1.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988   -0.6602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4034   -1.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4034    0.5776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    1.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034228

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)C(NC(C)=O)=C2SSC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)

> <INCHI_KEY>
MHMRAFONCSQAIA-UHFFFAOYSA-N

> <FORMULA>
C8H8N2O2S2

> <MOLECULAR_WEIGHT>
228.291

> <EXACT_MASS>
228.00271889

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
21.952411352473877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}acetamide

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
-0.5274866153333333

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.501974404604912

> <JCHEM_PKA_STRONGEST_BASIC>
-4.620144100700394

> <JCHEM_POLAR_SURFACE_AREA>
49.410000000000004

> <JCHEM_REFRACTIVITY>
60.346500000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiolutin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0034228 (Thiolutin)

HMDB0034228
     RDKit          3D
Thiolutin
 22 23  0  0  0  0  0  0  0  0999 V2000
    4.1526    0.4366   -0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7025    0.5776    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926    1.3882    1.1747 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102   -0.1670   -0.3791 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3288   -0.1262   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691    0.6257    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1921    1.8089    1.9131 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729    2.0680    2.4127 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7820    0.9378    1.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562    0.2942    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8229   -0.6513   -0.4815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0087   -1.3005   -1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5677   -0.8958   -0.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2372   -1.7328   -1.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3371    0.0117   -1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531   -0.2983    0.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6338    1.4196    0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -0.8326   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8909    0.7660    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4835   -0.5740   -1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193   -2.2256   -1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7277   -1.5302   -0.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13  5  1  0
 10  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  9 19  1  0
 12 20  1  0
 12 21  1  0
 12 22  1  0
M  END
Download

PDB for HMDB0034228 (Thiolutin)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.232   0.155   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      -2.620  -0.307   0.000  0.00  0.00           S+0
HETATM    3  S   UNK     0      -3.544   0.924   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      -2.620   2.157   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.232   1.695   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.155   2.157   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.078   0.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.307  -0.307   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.770  -1.695   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.311  -2.157   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.544  -1.232   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.620  -3.699   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.620   1.078   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.770   3.699   0.000  0.00  0.00           C+0
CONECT    1    2    5    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4    6                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   13                                                  
CONECT    8    1    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7                                                            
CONECT   14    6                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for HMDB0034228 (Thiolutin)

COMPND    HMDB0034228
HETATM    1  C1  UNL     1       4.153   0.437  -0.026  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.703   0.578   0.288  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.393   1.388   1.175  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.710  -0.167  -0.379  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.329  -0.126  -0.178  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.469   0.626   0.703  1.00  0.00           C  
HETATM    7  S1  UNL     1      -0.192   1.809   1.913  1.00  0.00           S  
HETATM    8  S2  UNL     1      -2.173   2.068   2.413  1.00  0.00           S  
HETATM    9  C5  UNL     1      -2.782   0.938   1.297  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.856   0.294   0.515  1.00  0.00           C  
HETATM   11  N2  UNL     1      -1.823  -0.651  -0.482  1.00  0.00           N  
HETATM   12  C7  UNL     1      -3.009  -1.301  -1.027  1.00  0.00           C  
HETATM   13  C8  UNL     1      -0.568  -0.896  -0.882  1.00  0.00           C  
HETATM   14  O2  UNL     1      -0.237  -1.733  -1.799  1.00  0.00           O  
HETATM   15  H1  UNL     1       4.337   0.012  -1.020  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.553  -0.298   0.719  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.634   1.420   0.098  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.119  -0.833  -1.125  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.891   0.766   1.244  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.483  -0.574  -1.731  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.719  -2.226  -1.531  1.00  0.00           H  
HETATM   22  H8  UNL     1      -3.728  -1.530  -0.186  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3    4
CONECT    4    5   18
CONECT    5    6    6   13
CONECT    6    7   10
CONECT    7    8
CONECT    8    9
CONECT    9   10   10   19
CONECT   10   11
CONECT   11   12   13
CONECT   12   20   21   22
CONECT   13   14   14
END
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SMILES for HMDB0034228 (Thiolutin)

CN1C(=O)C(NC(C)=O)=C2SSC=C12
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INCHI for HMDB0034228 (Thiolutin)

InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
6-Acetamido-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-oneChEBI
AcetopyrrothinChEBI
AcetopyrrothineChEBI
N-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)acetamideChEBI
N-(4-Methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamideChEBI
FarcinicineHMDB
N-AcetylpyrrothineHMDB
N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}ethanimidateGenerator
ThiolutinMeSH
Chemical FormulaC8H8N2O2S2
Average Molecular Weight228.291
Monoisotopic Molecular Weight228.00271889
IUPAC NameN-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}acetamide
Traditional Namethiolutin
CAS Registry Number87-11-6
SMILES
CN1C(=O)C(NC(C)=O)=C2SSC=C12
InChI Identifier
InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)
InChI KeyMHMRAFONCSQAIA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acetylarylamines. These are acetamides where one or more amide hydrogens is substituted by an aryl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassN-arylamides
Direct ParentN-acetylarylamines
Alternative Parents
Substituents
  • N-acetylarylamine
  • N-methylpyrrole
  • Substituted pyrrole
  • Pyrrole
  • 1,2-dithiole
  • Dithiole
  • Acetamide
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Lactam
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point273 - 276 °CNot Available
Boiling Point152.00 to 156.00 °C. @ 17.00 mm HgThe Good Scents Company Information System
Water Solubility0.21 mg/mLNot Available
LogP2.298 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.73 g/LALOGPS
logP0.82ALOGPS
logP-0.53ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.5ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.41 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.35 m³·mol⁻¹ChemAxon
Polarizability21.95 ųChemAxon
Number of Rings2ChemAxon
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]+148.50831661259
DarkChem[M-H]-140.81531661259
DeepCCS[M-2H]-171.86330932474
DeepCCS[M+Na]+146.66230932474
AllCCS[M+H]+145.032859911
AllCCS[M+H-H2O]+141.132859911
AllCCS[M+NH4]+148.632859911
AllCCS[M+Na]+149.732859911
AllCCS[M-H]-144.632859911
AllCCS[M+Na-2H]-145.032859911
AllCCS[M+HCOO]-145.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.31 minutes32390414
Predicted by Siyang on May 30, 202212.3403 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.73 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1668.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid383.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid122.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid240.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid92.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid390.2 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 Acid630.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)315.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid924.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid366.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1266.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid309.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid317.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate526.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA341.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water123.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ThiolutinCN1C(=O)C(NC(C)=O)=C2SSC=C122886.1Standard polar33892256
ThiolutinCN1C(=O)C(NC(C)=O)=C2SSC=C122012.4Standard non polar33892256
ThiolutinCN1C(=O)C(NC(C)=O)=C2SSC=C122207.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Thiolutin,1TMS,isomer #1CC(=O)N(C1=C2SSC=C2N(C)C1=O)[Si](C)(C)C2063.8Semi standard non polar33892256
Thiolutin,1TMS,isomer #1CC(=O)N(C1=C2SSC=C2N(C)C1=O)[Si](C)(C)C2282.2Standard non polar33892256
Thiolutin,1TBDMS,isomer #1CC(=O)N(C1=C2SSC=C2N(C)C1=O)[Si](C)(C)C(C)(C)C2276.3Semi standard non polar33892256
Thiolutin,1TBDMS,isomer #1CC(=O)N(C1=C2SSC=C2N(C)C1=O)[Si](C)(C)C(C)(C)C2550.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Thiolutin GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-3910000000-519ee727a019d3a93d692017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thiolutin 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 - Thiolutin 10V, Positive-QTOFsplash10-004i-7590000000-85817f7eb87b0115bd932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiolutin 20V, Positive-QTOFsplash10-004r-0590000000-515631cb29113ba3b9622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiolutin 40V, Positive-QTOFsplash10-052s-9200000000-f7ff9dbd9f3a2082f78f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiolutin 10V, Negative-QTOFsplash10-004i-0890000000-9e6266701a4ec9c610602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiolutin 20V, Negative-QTOFsplash10-003r-1970000000-03b1d843e3d93fbf40bc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiolutin 40V, Negative-QTOFsplash10-0zgi-2900000000-2d15a380d25bc120cdf32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiolutin 10V, Positive-QTOFsplash10-002r-0980000000-5f26834e99b886e3f03b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiolutin 20V, Positive-QTOFsplash10-002r-0960000000-7693ffa3bb0a88d601d72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiolutin 40V, Positive-QTOFsplash10-0159-2900000000-a10fda5b87d577f08ad22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiolutin 10V, Negative-QTOFsplash10-004i-0090000000-95faf19c58c835a83e002021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiolutin 20V, Negative-QTOFsplash10-0059-0590000000-0ab84e20d5f22fd4f7af2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiolutin 40V, Negative-QTOFsplash10-004i-1920000000-229b3b69617b7784c3572021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB012539
KNApSAcK IDC00054277
Chemspider ID6608
KEGG Compound IDNot Available
BioCyc IDCPD-17934
BiGG IDNot Available
Wikipedia LinkThiolutin
METLIN IDNot Available
PubChem Compound6870
PDB IDNot Available
ChEBI ID156450
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1021681
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Dai S, Jia Y, Wu SL, Isenberg JS, Ridnour LA, Bandle RW, Wink DA, Roberts DD, Karger BL: Comprehensive characterization of heat shock protein 27 phosphorylation in human endothelial cells stimulated by the microbial dithiole thiolutin. J Proteome Res. 2008 Oct;7(10):4384-95. doi: 10.1021/pr800376w. Epub 2008 Aug 23. [PubMed:18720982 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .