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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:45:48 UTC

Update Date

2021-09-26 23:00:00 UTC

HMDB ID

HMDB0249258

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bisdethiobis(methylthio)gliotoxin

Description

Bis(methylthio)gliotoxin(fr-49175) belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review very few articles have been published on Bis(methylthio)gliotoxin(fr-49175). This compound has been identified in human blood as reported by (PMID: 31557052 ). Bisdethiobis(methylthio)gliotoxin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bisdethiobis(methylthio)gliotoxin 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

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

HMDB0249258
     RDKit          3D
Bisdethiobis(methylthio)gliotoxin
 43 45  0  0  0  0  0  0  0  0999 V2000
    3.8366   -1.4963    1.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729    0.0816    0.5765 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -0.1232   -0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1737   -0.9150   -1.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1326   -0.2371   -2.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7499   -0.9068    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964   -2.1253    0.5100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5181   -0.3946    0.5274 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744   -0.9323    0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770    0.2036    0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6490    0.0846   -0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0222   -1.1964   -1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3027   -2.2375   -0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1683   -2.2137    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940   -3.2459    1.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0538    1.4166    0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5814    1.0501    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559    1.4700    2.3315 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1451    3.2309    2.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964    1.7049   -0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3894    2.7360   -0.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    1.1615   -0.8601 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0223    1.9625   -1.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6068   -2.3224    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418   -1.4295    1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4100   -1.6723    2.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -1.1100   -2.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5612   -1.9201   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7626   -0.9027   -2.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0486   -0.9792    1.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2104    1.0038   -0.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8206   -1.3196   -1.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5436   -3.2469   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2464   -2.4969   -0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3757   -4.0914    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2129    2.3358    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4338    1.5097    1.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413    3.6596    2.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5450    3.5057    3.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2181    3.7694    1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7135    3.0327   -1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    1.6350   -2.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1193    1.9610   -1.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22  3  1  0
 17  8  1  0
 14  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
M  END

  Mrv1533004241505332D          

 23 25  0  0  0  0            999 V2000
    0.6500   -1.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1580   -1.9474    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9461   -2.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2177   -3.0444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7200   -1.0479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9130   -0.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171    0.3498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7464   -0.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4139   -0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2208   -0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7729   -1.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5179   -1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7110   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4560   -2.7887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1589   -1.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339   -1.3910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368   -2.7887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9075    0.2006    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5206    0.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249258

> <DATABASE_NAME>
hmdb

> <SMILES>
CSC12CC3=CC=CC(O)C3N1C(=O)C(CO)(SC)N(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20N2O4S2/c1-16-12(20)14(22-2)7-9-5-4-6-10(19)11(9)17(14)13(21)15(16,8-18)23-3/h4-6,10-11,18-19H,7-8H2,1-3H3

> <INCHI_KEY>
OVBAGMZLGLXSBN-UHFFFAOYSA-N

> <FORMULA>
C15H20N2O4S2

> <MOLECULAR_WEIGHT>
356.46

> <EXACT_MASS>
356.08644948

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.33527793516839

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-1H,2H,3H,4H,5aH,6H,10H,10aH-piperazino[1,2-a]indole-1,4-dione

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
0.6107173760000006

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.458619372895111

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.854282942268522

> <JCHEM_PKA_STRONGEST_BASIC>
-3.154018580541682

> <JCHEM_POLAR_SURFACE_AREA>
81.07999999999998

> <JCHEM_REFRACTIVITY>
92.78579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-5aH,6H,10H-piperazino[1,2-a]indole-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249258
     RDKit          3D
Bisdethiobis(methylthio)gliotoxin
 43 45  0  0  0  0  0  0  0  0999 V2000
    3.8366   -1.4963    1.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729    0.0816    0.5765 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -0.1232   -0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1737   -0.9150   -1.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1326   -0.2371   -2.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7499   -0.9068    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964   -2.1253    0.5100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5181   -0.3946    0.5274 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744   -0.9323    0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770    0.2036    0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6490    0.0846   -0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0222   -1.1964   -1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3027   -2.2375   -0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1683   -2.2137    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940   -3.2459    1.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0538    1.4166    0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5814    1.0501    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559    1.4700    2.3315 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1451    3.2309    2.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964    1.7049   -0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3894    2.7360   -0.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    1.1615   -0.8601 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0223    1.9625   -1.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6068   -2.3224    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418   -1.4295    1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4100   -1.6723    2.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -1.1100   -2.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5612   -1.9201   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7626   -0.9027   -2.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0486   -0.9792    1.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2104    1.0038   -0.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8206   -1.3196   -1.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5436   -3.2469   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2464   -2.4969   -0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3757   -4.0914    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2129    2.3358    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4338    1.5097    1.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413    3.6596    2.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5450    3.5057    3.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2181    3.7694    1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7135    3.0327   -1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    1.6350   -2.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1193    1.9610   -1.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22  3  1  0
 17  8  1  0
 14  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.213  -2.422   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       2.162  -3.635   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       3.687  -3.421   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.633  -4.960   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.273  -5.683   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       3.211  -1.956   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.704  -1.636   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.241  -0.812   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.765   0.653   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.747  -1.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.993  -0.227   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.239  -1.132   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.746  -0.812   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.776  -1.956   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.300  -3.421   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.794  -3.741   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.318  -5.206   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.763  -2.597   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       6.223  -2.597   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.193  -3.741   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.669  -5.206   0.000  0.00  0.00           O+0
HETATM   22  S   UNK     0       5.427   0.374   0.000  0.00  0.00           S+0
HETATM   23  C   UNK     0       6.572   1.405   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6   20                                             
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   19   22                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18   10   20                                                  
CONECT   20   19    3   21                                                  
CONECT   21   20                                                            
CONECT   22   10   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0249258
HETATM    1  C1  UNL     1       3.837  -1.496   1.248  1.00  0.00           C  
HETATM    2  S1  UNL     1       3.273   0.082   0.577  1.00  0.00           S  
HETATM    3  C2  UNL     1       1.817  -0.123  -0.478  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.174  -0.915  -1.720  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.133  -0.237  -2.421  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.750  -0.907   0.201  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.996  -2.125   0.510  1.00  0.00           O  
HETATM    8  N1  UNL     1      -0.518  -0.395   0.527  1.00  0.00           N  
HETATM    9  C5  UNL     1      -1.874  -0.932   0.677  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.677   0.204   0.222  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.649   0.085  -0.623  1.00  0.00           C  
HETATM   12  C8  UNL     1      -4.022  -1.196  -1.213  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.303  -2.238  -0.855  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.168  -2.214   0.068  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.294  -3.246   1.041  1.00  0.00           O  
HETATM   16  C11 UNL     1      -2.054   1.417   0.888  1.00  0.00           C  
HETATM   17  C12 UNL     1      -0.581   1.050   0.806  1.00  0.00           C  
HETATM   18  S2  UNL     1       0.256   1.470   2.331  1.00  0.00           S  
HETATM   19  C13 UNL     1       0.145   3.231   2.636  1.00  0.00           C  
HETATM   20  C14 UNL     1       0.096   1.705  -0.327  1.00  0.00           C  
HETATM   21  O4  UNL     1      -0.389   2.736  -0.818  1.00  0.00           O  
HETATM   22  N2  UNL     1       1.304   1.162  -0.860  1.00  0.00           N  
HETATM   23  C15 UNL     1       2.022   1.962  -1.822  1.00  0.00           C  
HETATM   24  H1  UNL     1       3.607  -2.322   0.548  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.942  -1.430   1.373  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.410  -1.672   2.272  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.279  -1.110  -2.345  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.561  -1.920  -1.437  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.763  -0.903  -2.815  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.049  -0.979   1.836  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.210   1.004  -0.898  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.821  -1.320  -1.895  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.544  -3.247  -1.268  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.246  -2.497  -0.569  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.376  -4.091   0.561  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.213   2.336   0.345  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.434   1.510   1.913  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.141   3.660   2.873  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.545   3.506   3.462  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.218   3.769   1.737  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.714   3.033  -1.741  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.847   1.635  -2.879  1.00  0.00           H  
HETATM   43  H20 UNL     1       3.119   1.961  -1.668  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    6   22
CONECT    4    5   27   28
CONECT    5   29
CONECT    6    7    7    8
CONECT    8    9   17
CONECT    9   10   14   30
CONECT   10   11   11   16
CONECT   11   12   31
CONECT   12   13   13   32
CONECT   13   14   33
CONECT   14   15   34
CONECT   15   35
CONECT   16   17   36   37
CONECT   17   18   20
CONECT   18   19
CONECT   19   38   39   40
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   41   42   43
END

HMDB0249258
     RDKit          3D
Bisdethiobis(methylthio)gliotoxin
 43 45  0  0  0  0  0  0  0  0999 V2000
    3.8366   -1.4963    1.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2729    0.0816    0.5765 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -0.1232   -0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1737   -0.9150   -1.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1326   -0.2371   -2.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7499   -0.9068    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964   -2.1253    0.5100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5181   -0.3946    0.5274 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744   -0.9323    0.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770    0.2036    0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6490    0.0846   -0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0222   -1.1964   -1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3027   -2.2375   -0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1683   -2.2137    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940   -3.2459    1.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0538    1.4166    0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5814    1.0501    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559    1.4700    2.3315 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1451    3.2309    2.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964    1.7049   -0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3894    2.7360   -0.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    1.1615   -0.8601 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0223    1.9625   -1.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6068   -2.3224    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418   -1.4295    1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4100   -1.6723    2.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -1.1100   -2.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5612   -1.9201   -1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7626   -0.9027   -2.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0486   -0.9792    1.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2104    1.0038   -0.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8206   -1.3196   -1.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5436   -3.2469   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2464   -2.4969   -0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3757   -4.0914    0.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2129    2.3358    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4338    1.5097    1.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413    3.6596    2.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5450    3.5057    3.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2181    3.7694    1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7135    3.0327   -1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    1.6350   -2.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1193    1.9610   -1.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22  3  1  0
 17  8  1  0
 14  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-Hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulphanyl)-1H,2H,3H,4H,5ah,6H,10H,10ah-pyrazino[1,2-a]indole-1,4-dione	Generator

Chemical Formula

C₁₅H₂₀N₂O₄S₂

Average Molecular Weight

356.46

Monoisotopic Molecular Weight

356.08644948

IUPAC Name

6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-1H,2H,3H,4H,5aH,6H,10H,10aH-piperazino[1,2-a]indole-1,4-dione

Traditional Name

6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-5aH,6H,10H-piperazino[1,2-a]indole-1,4-dione

CAS Registry Number

Not Available

SMILES

CSC12CC3=CC=CC(O)C3N1C(=O)C(CO)(SC)N(C)C2=O

InChI Identifier

InChI=1S/C15H20N2O4S2/c1-16-12(20)14(22-2)7-9-5-4-6-10(19)11(9)17(14)13(21)15(16,8-18)23-3/h4-6,10-11,18-19H,7-8H2,1-3H3

InChI Key

OVBAGMZLGLXSBN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Indole or derivatives
Thiodioxopiperazine
Dioxopiperazine
2,5-dioxopiperazine
N-methylpiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Organoheterocyclic compound
Dialkylthioether
Azacycle
Sulfenyl compound
Hemithioaminal
Thioether
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxide
Organic oxygen compound
Organosulfur compound
Carbonyl group
Primary alcohol
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	-0.12	ALOGPS
logP	0.61	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.08 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.79 m³·mol⁻¹	ChemAxon
Polarizability	35.34 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	214.738	30932474
DeepCCS	[M+Na]+	189.965	30932474
AllCCS	[M+H]+	180.4	32859911
AllCCS	[M+H-H2O]+	177.7	32859911
AllCCS	[M+NH4]+	182.9	32859911
AllCCS	[M+Na]+	183.6	32859911
AllCCS	[M-H]-	180.5	32859911
AllCCS	[M+Na-2H]-	180.6	32859911
AllCCS	[M+HCOO]-	180.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bisdethiobis(methylthio)gliotoxin	CSC12CC3=CC=CC(O)C3N1C(=O)C(CO)(SC)N(C)C2=O	4443.7	Standard polar	33892256
Bisdethiobis(methylthio)gliotoxin	CSC12CC3=CC=CC(O)C3N1C(=O)C(CO)(SC)N(C)C2=O	2692.8	Standard non polar	33892256
Bisdethiobis(methylthio)gliotoxin	CSC12CC3=CC=CC(O)C3N1C(=O)C(CO)(SC)N(C)C2=O	2901.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bisdethiobis(methylthio)gliotoxin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7i-4953000000-360a73e94ca7300fd361	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisdethiobis(methylthio)gliotoxin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisdethiobis(methylthio)gliotoxin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisdethiobis(methylthio)gliotoxin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisdethiobis(methylthio)gliotoxin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisdethiobis(methylthio)gliotoxin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisdethiobis(methylthio)gliotoxin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bisdethiobis(methylthio)gliotoxin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - Bisdethiobis(methylthio)gliotoxin 10V, Positive-QTOF	splash10-0a4i-0009000000-f60543432a2d9ec1aa15	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdethiobis(methylthio)gliotoxin 20V, Positive-QTOF	splash10-0a4i-0049000000-6781c52feb583582092e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdethiobis(methylthio)gliotoxin 40V, Positive-QTOF	splash10-0fai-4895000000-8ff21398e2ff122850b9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdethiobis(methylthio)gliotoxin 10V, Negative-QTOF	splash10-0a4i-0019000000-776a121521a9e3086baf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdethiobis(methylthio)gliotoxin 20V, Negative-QTOF	splash10-08i0-0092000000-c413823e81e5768cd4e1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bisdethiobis(methylthio)gliotoxin 40V, Negative-QTOF	splash10-0002-7592000000-10358d276c8e9e78b169	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

4289254

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5114266

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

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 ]

Showing metabocard for Bisdethiobis(methylthio)gliotoxin (HMDB0249258)

MOL for HMDB0249258 (Bisdethiobis(methylthio)gliotoxin)

3D MOL for HMDB0249258 (Bisdethiobis(methylthio)gliotoxin)

3D SDF for HMDB0249258 (Bisdethiobis(methylthio)gliotoxin)

3D-SDF for HMDB0249258 (Bisdethiobis(methylthio)gliotoxin)

PDB for HMDB0249258 (Bisdethiobis(methylthio)gliotoxin)

3D PDB for HMDB0249258 (Bisdethiobis(methylthio)gliotoxin)

SMILES for HMDB0249258 (Bisdethiobis(methylthio)gliotoxin)

INCHI for HMDB0249258 (Bisdethiobis(methylthio)gliotoxin)

Structure for HMDB0249258 (Bisdethiobis(methylthio)gliotoxin)

3D Structure for HMDB0249258 (Bisdethiobis(methylthio)gliotoxin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra