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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:51:30 UTC

Update Date

2022-11-23 22:29:20 UTC

HMDB ID

HMDB0258971

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Thiamiprine

Description

Thiamiprine, also known as guaneran, belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups. Based on a literature review very few articles have been published on Thiamiprine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Thiamiprine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Thiamiprine 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

HMDB0258971
     RDKit          3D
THIAMIPRINE
 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.2802    1.4565   -1.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5637    0.5769   -0.6295 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6031   -0.2525   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5639   -0.9069    0.5906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4865   -0.4775    1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0574   -0.8959    2.5301 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.8614   -0.9135    2.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9766   -1.2796    3.4494 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.8209    0.4843    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    1.3460    0.9499 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579    0.6489    0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792    1.3132    0.8405 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278    0.9194    0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6626    1.6613    0.9680 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6728   -0.2422   -0.1459 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6267   -0.9772   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4435   -2.1155   -1.2345 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383   -2.3790   -1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652   -1.3757   -0.7202 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3471   -0.5141   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098    0.9285   -2.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111    2.4321   -1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1871    1.6645   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926   -0.4189   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7828    1.9013    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3570    1.9539    0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744   -3.2234   -1.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -1.3146   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
  9  2  1  0
 20 11  1  0
 20 16  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
 14 25  1  0
 14 26  1  0
 18 27  1  0
 19 28  1  0
M  CHG  2   6   1   8  -1
M  END

  Mrv1652309112122512D          

 20 22  0  0  0  0            999 V2000
    4.9186    1.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7471    2.1394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2991    2.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866    3.4670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796    3.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4665    3.8475    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.6381    4.6545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819    3.5926    0.0000 O   0  5  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 12 16  1  0  0  0  0
 10 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  CHG  2  18   1  20  -1
M  END
> <DATABASE_ID>
HMDB0258971

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=NC(=C1SC1=NC(N)=NC2=C1NC=N2)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H8N8O2S/c1-16-3-13-6(17(18)19)8(16)20-7-4-5(12-2-11-4)14-9(10)15-7/h2-3H,1H3,(H3,10,11,12,14,15)

> <INCHI_KEY>
YFTWHEBLORWGNI-UHFFFAOYSA-N

> <FORMULA>
C9H8N8O2S

> <MOLECULAR_WEIGHT>
292.28

> <EXACT_MASS>
292.049092704

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
25.986253279138673

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purin-2-amine

> <ALOGPS_LOGP>
0.29

> <JCHEM_LOGP>
1.0230040256666668

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.224359843821949

> <JCHEM_PKA_STRONGEST_BASIC>
2.6426546177636636

> <JCHEM_POLAR_SURFACE_AREA>
141.44

> <JCHEM_REFRACTIVITY>
74.58839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(3-methyl-5-nitroimidazol-4-yl)sulfanyl]-7H-purin-2-amine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258971
     RDKit          3D
THIAMIPRINE
 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.2802    1.4565   -1.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5637    0.5769   -0.6295 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6031   -0.2525   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5639   -0.9069    0.5906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4865   -0.4775    1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0574   -0.8959    2.5301 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.8614   -0.9135    2.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9766   -1.2796    3.4494 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.8209    0.4843    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    1.3460    0.9499 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579    0.6489    0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792    1.3132    0.8405 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278    0.9194    0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6626    1.6613    0.9680 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6728   -0.2422   -0.1459 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6267   -0.9772   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4435   -2.1155   -1.2345 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383   -2.3790   -1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652   -1.3757   -0.7202 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3471   -0.5141   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098    0.9285   -2.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111    2.4321   -1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1871    1.6645   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926   -0.4189   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7828    1.9013    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3570    1.9539    0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744   -3.2234   -1.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -1.3146   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
  9  2  1  0
 20 11  1  0
 20 16  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
 14 25  1  0
 14 26  1  0
 18 27  1  0
 19 28  1  0
M  CHG  2   6   1   8  -1
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       9.181   2.487   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       8.861   3.994   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.892   5.138   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       9.122   6.472   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.615   6.152   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       6.121   3.850   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.454   1.540   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       8.788  -0.770   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       6.471   7.182   0.000  0.00  0.00           N+1
HETATM   19  O   UNK     0       6.791   8.688   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.006   6.706   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   10                                                            
CONECT   18    5   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0258971
HETATM    1  C1  UNL     1      -2.280   1.457  -1.755  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.564   0.577  -0.630  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.603  -0.253  -0.572  1.00  0.00           C  
HETATM    4  N2  UNL     1      -3.564  -0.907   0.591  1.00  0.00           N  
HETATM    5  C3  UNL     1      -2.487  -0.478   1.262  1.00  0.00           C  
HETATM    6  N3  UNL     1      -2.057  -0.896   2.530  1.00  0.00           N1+
HETATM    7  O1  UNL     1      -0.861  -0.914   2.802  1.00  0.00           O  
HETATM    8  O2  UNL     1      -2.977  -1.280   3.449  1.00  0.00           O1-
HETATM    9  C4  UNL     1      -1.821   0.484   0.493  1.00  0.00           C  
HETATM   10  S1  UNL     1      -0.375   1.346   0.950  1.00  0.00           S  
HETATM   11  C5  UNL     1       1.158   0.649   0.479  1.00  0.00           C  
HETATM   12  N4  UNL     1       2.279   1.313   0.841  1.00  0.00           N  
HETATM   13  C6  UNL     1       3.528   0.919   0.560  1.00  0.00           C  
HETATM   14  N5  UNL     1       4.663   1.661   0.968  1.00  0.00           N  
HETATM   15  N6  UNL     1       3.673  -0.242  -0.146  1.00  0.00           N  
HETATM   16  C7  UNL     1       2.627  -0.977  -0.553  1.00  0.00           C  
HETATM   17  N7  UNL     1       2.443  -2.115  -1.235  1.00  0.00           N  
HETATM   18  C8  UNL     1       1.138  -2.379  -1.349  1.00  0.00           C  
HETATM   19  N8  UNL     1       0.465  -1.376  -0.720  1.00  0.00           N  
HETATM   20  C9  UNL     1       1.347  -0.514  -0.229  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.610   0.928  -2.672  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.811   2.432  -1.643  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.187   1.665  -1.843  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.393  -0.419  -1.315  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.783   1.901   1.958  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.357   1.954   0.272  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.674  -3.223  -1.844  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.547  -1.315  -0.650  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    9
CONECT    3    4    4   24
CONECT    4    5
CONECT    5    6    9    9
CONECT    6    7    7    8
CONECT    9   10
CONECT   10   11
CONECT   11   12   12   20
CONECT   12   13
CONECT   13   14   15   15
CONECT   14   25   26
CONECT   15   16
CONECT   16   17   20   20
CONECT   17   18   18
CONECT   18   19   27
CONECT   19   20   28
END

HMDB0258971
     RDKit          3D
THIAMIPRINE
 28 30  0  0  0  0  0  0  0  0999 V2000
   -2.2802    1.4565   -1.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5637    0.5769   -0.6295 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6031   -0.2525   -0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5639   -0.9069    0.5906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4865   -0.4775    1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0574   -0.8959    2.5301 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.8614   -0.9135    2.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9766   -1.2796    3.4494 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.8209    0.4843    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    1.3460    0.9499 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579    0.6489    0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792    1.3132    0.8405 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278    0.9194    0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6626    1.6613    0.9680 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6728   -0.2422   -0.1459 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6267   -0.9772   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4435   -2.1155   -1.2345 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383   -2.3790   -1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652   -1.3757   -0.7202 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3471   -0.5141   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098    0.9285   -2.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111    2.4321   -1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1871    1.6645   -1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926   -0.4189   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7828    1.9013    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3570    1.9539    0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744   -3.2234   -1.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -1.3146   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
  9  2  1  0
 20 11  1  0
 20 16  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
 14 25  1  0
 14 26  1  0
 18 27  1  0
 19 28  1  0
M  CHG  2   6   1   8  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-[(1-Methyl-4-nitro-1H-imidazol-5-yl)sulphanyl]-3,9-dihydro-2H-purin-2-imine	HMDB
6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purin-2-amine	HMDB
Guaneran	HMDB

Chemical Formula

C₉H₈N₈O₂S

Average Molecular Weight

292.28

Monoisotopic Molecular Weight

292.049092704

IUPAC Name

6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purin-2-amine

Traditional Name

6-[(3-methyl-5-nitroimidazol-4-yl)sulfanyl]-7H-purin-2-amine

CAS Registry Number

Not Available

SMILES

CN1C=NC(=C1SC1=NC(N)=NC2=C1NC=N2)[N+]([O-])=O

InChI Identifier

InChI=1S/C9H8N8O2S/c1-16-3-13-6(17(18)19)8(16)20-7-4-5(12-2-11-4)14-9(10)15-7/h2-3H,1H3,(H3,10,11,12,14,15)

InChI Key

YFTWHEBLORWGNI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Aryl thioethers

Direct Parent

Diarylthioethers

Alternative Parents

Substituents

Diarylthioether
6-thiopurine
Imidazopyrimidine
Purine
Nitroaromatic compound
Nitroimidazole
Aminopyrimidine
N-substituted imidazole
Imidolactam
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
C-nitro compound
Organic nitro compound
Azacycle
Organoheterocyclic compound
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Amine
Organonitrogen compound
Primary amine
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.29	ALOGPS
logP	1.02	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	10.22	ChemAxon
pKa (Strongest Basic)	2.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	141.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.59 m³·mol⁻¹	ChemAxon
Polarizability	25.99 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+H]+	147.65	30932474
DeepCCS	[M-H]-	145.077	30932474
DeepCCS	[M-2H]-	179.516	30932474
DeepCCS	[M+Na]+	155.542	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.7	32859911
AllCCS	[M+NH4]+	166.4	32859911
AllCCS	[M+Na]+	167.3	32859911
AllCCS	[M-H]-	159.3	32859911
AllCCS	[M+Na-2H]-	158.7	32859911
AllCCS	[M+HCOO]-	158.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
THIAMIPRINE	CN1C=NC(=C1SC1=NC(N)=NC2=C1NC=N2)[N+]([O-])=O	3341.9	Standard polar	33892256
THIAMIPRINE	CN1C=NC(=C1SC1=NC(N)=NC2=C1NC=N2)[N+]([O-])=O	2930.1	Standard non polar	33892256
THIAMIPRINE	CN1C=NC(=C1SC1=NC(N)=NC2=C1NC=N2)[N+]([O-])=O	3407.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
THIAMIPRINE,1TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C)=NC2=C1[NH]C=N2	3138.6	Semi standard non polar	33892256
THIAMIPRINE,1TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C)=NC2=C1[NH]C=N2	3082.4	Standard non polar	33892256
THIAMIPRINE,1TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C)=NC2=C1[NH]C=N2	4821.1	Standard polar	33892256
THIAMIPRINE,1TMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N)=NC2=C1N([Si](C)(C)C)C=N2	3127.8	Semi standard non polar	33892256
THIAMIPRINE,1TMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N)=NC2=C1N([Si](C)(C)C)C=N2	2858.5	Standard non polar	33892256
THIAMIPRINE,1TMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N)=NC2=C1N([Si](C)(C)C)C=N2	4571.9	Standard polar	33892256
THIAMIPRINE,2TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1[NH]C=N2	3026.8	Semi standard non polar	33892256
THIAMIPRINE,2TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1[NH]C=N2	3156.2	Standard non polar	33892256
THIAMIPRINE,2TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1[NH]C=N2	4379.1	Standard polar	33892256
THIAMIPRINE,2TMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C=N2	3095.4	Semi standard non polar	33892256
THIAMIPRINE,2TMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C=N2	2874.1	Standard non polar	33892256
THIAMIPRINE,2TMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C=N2	4341.3	Standard polar	33892256
THIAMIPRINE,3TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C=N2	3071.9	Semi standard non polar	33892256
THIAMIPRINE,3TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C=N2	2985.9	Standard non polar	33892256
THIAMIPRINE,3TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1N([Si](C)(C)C)C=N2	3880.4	Standard polar	33892256
THIAMIPRINE,1TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C=N2	3305.4	Semi standard non polar	33892256
THIAMIPRINE,1TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C=N2	3313.7	Standard non polar	33892256
THIAMIPRINE,1TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C=N2	4726.0	Standard polar	33892256
THIAMIPRINE,1TBDMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	3327.8	Semi standard non polar	33892256
THIAMIPRINE,1TBDMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	3047.2	Standard non polar	33892256
THIAMIPRINE,1TBDMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	4550.2	Standard polar	33892256
THIAMIPRINE,2TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C=N2	3399.8	Semi standard non polar	33892256
THIAMIPRINE,2TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C=N2	3586.0	Standard non polar	33892256
THIAMIPRINE,2TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1[NH]C=N2	4221.6	Standard polar	33892256
THIAMIPRINE,2TBDMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	3416.4	Semi standard non polar	33892256
THIAMIPRINE,2TBDMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	3307.2	Standard non polar	33892256
THIAMIPRINE,2TBDMS,isomer #2	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	4245.7	Standard polar	33892256
THIAMIPRINE,3TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	3597.3	Semi standard non polar	33892256
THIAMIPRINE,3TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	3596.4	Standard non polar	33892256
THIAMIPRINE,3TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1SC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2	3883.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamiprine GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-6970000000-01a76d2ae9b7c581de82	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamiprine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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

2624658

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3379405

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 Thiamiprine (HMDB0258971)

MOL for HMDB0258971 (Thiamiprine)

3D MOL for HMDB0258971 (Thiamiprine)

3D SDF for HMDB0258971 (Thiamiprine)

3D-SDF for HMDB0258971 (Thiamiprine)

PDB for HMDB0258971 (Thiamiprine)

3D PDB for HMDB0258971 (Thiamiprine)

SMILES for HMDB0258971 (Thiamiprine)

INCHI for HMDB0258971 (Thiamiprine)

Structure for HMDB0258971 (Thiamiprine)

3D Structure for HMDB0258971 (Thiamiprine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra