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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:16:24 UTC

Update Date

2019-07-23 07:15:42 UTC

HMDB ID

HMDB0061068

Secondary Accession Numbers

HMDB61068

Metabolite Identification

Common Name

S-methylazathioprine

Description

S-methylazathioprine is a metabolite of azathioprine. Azathioprine is a purine analogue immunosuppressive drug. It is used to prevent rejection following organ transplantation, and to treat a vast array of autoimmune diseases, including rheumatoid arthritis, pemphigus, inflammatory bowel disease, multiple sclerosis, autoimmune hepatitis, atopic dermatitis, myasthenia gravis, neuromyelitis optica or Devic's disease, restrictive lung disease, and others. (Wikipedia)

Structure

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

HMDB0061068
     RDKit          3D
S-methylazathioprine
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.5754   -1.3042   -2.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1379   -0.3052   -1.3260 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820    0.4932   -1.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4163    1.2863   -0.5252 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    0.9589    0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4207    1.5847    1.6772 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3452    1.7477    2.2428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5669    2.0192    2.2768 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6643   -0.0353   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531   -0.8449    0.6417 S   0  0  0  0  0  3  0  0  0  0  0  0
   -0.7355   -2.1479    1.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0854    0.0287    0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4850    0.5870    2.0847 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6221    1.2655    2.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    1.4103    1.2470 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389    0.8752    0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7966    0.8753   -1.1468 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0512    0.2032   -2.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386   -0.2151   -1.4160 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9694    0.1856   -0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0079   -2.3233   -1.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819   -1.3995   -2.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458   -1.0845   -3.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7444    0.4762   -2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0689   -3.0403    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7951   -2.4558    1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -1.8665    2.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8755    1.6971    3.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139    1.3149   -1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2871    0.0137   -3.0975 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
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  9  2  1  0
 20 12  1  0
 20 16  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 17 29  1  0
 18 30  1  0
M  CHG  3   6   1   8  -1  10   1
M  END


  Mrv0541 07091309162D          

 20 22  0  0  0  0            999 V2000
    4.9186   -0.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -1.6500    0.0000 C   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
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2991   -1.9275    0.0000 C   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
    4.0796   -2.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    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
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866   -2.6420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7471   -1.3144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4665   -3.0225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819   -2.7676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6381   -3.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  3  2  0  0  0  0
 11  6  1  0  0  0  0
 12  3  1  0  0  0  0
 12  7  1  0  0  0  0
 13  4  2  0  0  0  0
 13  7  1  0  0  0  0
 14  4  1  0  0  0  0
 14  9  2  0  0  0  0
 15  5  2  0  0  0  0
 15  8  1  0  0  0  0
 16  1  1  0  0  0  0
 16  5  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  1  0  0  0  0
 18 17  2  0  0  0  0
 19 17  2  0  0  0  0
 20  2  1  0  0  0  0
 20  9  1  0  0  0  0
 20 10  1  0  0  0  0
M  CHG  1  20   1
M  END
> <DATABASE_ID>
HMDB0061068

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C=NC(=C1[S+](C)C1=NC=NC2=C1N=CN2)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10N7O2S/c1-16-5-15-8(17(18)19)10(16)20(2)9-6-7(12-3-11-6)13-4-14-9/h3-5H,1-2H3,(H,11,12,13,14)/q+1

> <INCHI_KEY>
CAGKKYGOGIIIDP-UHFFFAOYSA-N

> <FORMULA>
C10H10N7O2S

> <MOLECULAR_WEIGHT>
292.297

> <EXACT_MASS>
292.061668289

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
26.702193253871574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl(1-methyl-4-nitro-1H-imidazol-5-yl)9H-purin-6-ylsulfanium

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
-0.3303754185426122

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.44682636943564

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9627856799489956

> <JCHEM_POLAR_SURFACE_AREA>
118.1

> <JCHEM_REFRACTIVITY>
72.83739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl(3-methyl-5-nitroimidazol-4-yl)9H-purin-6-ylsulfanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061068
     RDKit          3D
S-methylazathioprine
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.5754   -1.3042   -2.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1379   -0.3052   -1.3260 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820    0.4932   -1.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4163    1.2863   -0.5252 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    0.9589    0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4207    1.5847    1.6772 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3452    1.7477    2.2428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5669    2.0192    2.2768 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6643   -0.0353   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531   -0.8449    0.6417 S   0  0  0  0  0  3  0  0  0  0  0  0
   -0.7355   -2.1479    1.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0854    0.0287    0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4850    0.5870    2.0847 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6221    1.2655    2.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    1.4103    1.2470 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389    0.8752    0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7966    0.8753   -1.1468 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0512    0.2032   -2.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386   -0.2151   -1.4160 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9694    0.1856   -0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0079   -2.3233   -1.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819   -1.3995   -2.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458   -1.0845   -3.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7444    0.4762   -2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0689   -3.0403    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7951   -2.4558    1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -1.8665    2.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8755    1.6971    3.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139    1.3149   -1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2871    0.0137   -3.0975 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
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  9  2  1  0
 20 12  1  0
 20 16  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 17 29  1  0
 18 30  1  0
M  CHG  3   6   1   8  -1  10   1
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       9.181  -0.947   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.787  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.892  -3.598   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.615  -4.612   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       9.122  -4.932   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       8.861  -2.454   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       6.471  -5.642   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       5.006  -5.166   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.791  -7.148   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0       6.121  -2.310   0.000  0.00  0.00           S+1
CONECT    1   16                                                            
CONECT    2   20                                                            
CONECT    3   11   12                                                       
CONECT    4   13   14                                                       
CONECT    5   15   16                                                       
CONECT    6    7    9   11                                                  
CONECT    7    6   12   13                                                  
CONECT    8   10   15   17                                                  
CONECT    9    6   14   20                                                  
CONECT   10    8   16   20                                                  
CONECT   11    3    6                                                       
CONECT   12    3    7                                                       
CONECT   13    4    7                                                       
CONECT   14    4    9                                                       
CONECT   15    5    8                                                       
CONECT   16    1    5   10                                                  
CONECT   17    8   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    2    9   10                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0061068
HETATM    1  C1  UNL     1      -1.575  -1.304  -2.209  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.138  -0.305  -1.326  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.182   0.493  -1.580  1.00  0.00           C  
HETATM    4  N2  UNL     1      -3.416   1.286  -0.525  1.00  0.00           N  
HETATM    5  C3  UNL     1      -2.474   0.959   0.416  1.00  0.00           C  
HETATM    6  N3  UNL     1      -2.421   1.585   1.677  1.00  0.00           N1+
HETATM    7  O1  UNL     1      -1.345   1.748   2.243  1.00  0.00           O  
HETATM    8  O2  UNL     1      -3.567   2.019   2.277  1.00  0.00           O1-
HETATM    9  C4  UNL     1      -1.664  -0.035  -0.067  1.00  0.00           C  
HETATM   10  S1  UNL     1      -0.353  -0.845   0.642  1.00  0.00           S1+
HETATM   11  C5  UNL     1      -0.736  -2.148   1.718  1.00  0.00           C  
HETATM   12  C6  UNL     1       1.085   0.029   0.946  1.00  0.00           C  
HETATM   13  N4  UNL     1       1.485   0.587   2.085  1.00  0.00           N  
HETATM   14  C7  UNL     1       2.622   1.265   2.287  1.00  0.00           C  
HETATM   15  N5  UNL     1       3.462   1.410   1.247  1.00  0.00           N  
HETATM   16  C8  UNL     1       3.139   0.875   0.046  1.00  0.00           C  
HETATM   17  N6  UNL     1       3.797   0.875  -1.147  1.00  0.00           N  
HETATM   18  C9  UNL     1       3.051   0.203  -2.038  1.00  0.00           C  
HETATM   19  N7  UNL     1       1.939  -0.215  -1.416  1.00  0.00           N  
HETATM   20  C10 UNL     1       1.969   0.186  -0.134  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.008  -2.323  -1.996  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.482  -1.400  -2.131  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.846  -1.085  -3.273  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.744   0.476  -2.526  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.069  -3.040   1.545  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.795  -2.456   1.608  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.610  -1.867   2.806  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.876   1.697   3.269  1.00  0.00           H  
HETATM   29  H9  UNL     1       4.714   1.315  -1.345  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.287   0.014  -3.098  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   12
CONECT   11   25   26   27
CONECT   12   13   13   20
CONECT   13   14
CONECT   14   15   15   28
CONECT   15   16
CONECT   16   17   20   20
CONECT   17   18   29
CONECT   18   19   19   30
CONECT   19   20
END

HMDB0061068
     RDKit          3D
S-methylazathioprine
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.5754   -1.3042   -2.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1379   -0.3052   -1.3260 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820    0.4932   -1.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4163    1.2863   -0.5252 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742    0.9589    0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4207    1.5847    1.6772 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3452    1.7477    2.2428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5669    2.0192    2.2768 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6643   -0.0353   -0.0672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531   -0.8449    0.6417 S   0  0  0  0  0  3  0  0  0  0  0  0
   -0.7355   -2.1479    1.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0854    0.0287    0.9457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4850    0.5870    2.0847 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6221    1.2655    2.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    1.4103    1.2470 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1389    0.8752    0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7966    0.8753   -1.1468 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0512    0.2032   -2.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386   -0.2151   -1.4160 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9694    0.1856   -0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0079   -2.3233   -1.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819   -1.3995   -2.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8458   -1.0845   -3.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7444    0.4762   -2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0689   -3.0403    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7951   -2.4558    1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -1.8665    2.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8755    1.6971    3.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139    1.3149   -1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2871    0.0137   -3.0975 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
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  9  2  1  0
 20 12  1  0
 20 16  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 17 29  1  0
 18 30  1  0
M  CHG  3   6   1   8  -1  10   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₀N₇O₂S

Average Molecular Weight

292.297

Monoisotopic Molecular Weight

292.061668289

IUPAC Name

methyl(1-methyl-4-nitro-1H-imidazol-5-yl)9H-purin-6-ylsulfanium

Traditional Name

methyl(3-methyl-5-nitroimidazol-4-yl)9H-purin-6-ylsulfanium

CAS Registry Number

Not Available

SMILES

CN1C=NC(=C1[S+](C)C1=NC=NC2=C1N=CN2)N(=O)=O

InChI Identifier

InChI=1S/C10H10N7O2S/c1-16-5-15-8(17(18)19)10(16)20(2)9-6-7(12-3-11-6)13-4-14-9/h3-5H,1-2H3,(H,11,12,13,14)/q+1

InChI Key

CAGKKYGOGIIIDP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purines and purine derivatives

Alternative Parents

Substituents

Purine
Nitroaromatic compound
Nitroimidazole
N-substituted imidazole
Imidolactam
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
C-nitro compound
Organic nitro compound
Azacycle
Organic oxoazanium
Organic nitrogen compound
Organic oxygen compound
Organosulfur compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0061068)
Liver (HMDB: HMDB0061068)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061068)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061068)

Cellular substructure

Cytoplasm (HMDB: HMDB0061068)

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
Water Solubility	0.23 g/L	ALOGPS
logP	1.47	ALOGPS
logP	-0.33	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.45	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	118.1 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.84 m³·mol⁻¹	ChemAxon
Polarizability	26.7 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]+	159.388	30932474
DeepCCS	[M-H]-	157.03	30932474
DeepCCS	[M-2H]-	189.936	30932474
DeepCCS	[M+Na]+	165.481	30932474
AllCCS	[M+H]+	161.5	32859911
AllCCS	[M+H-H2O]+	158.2	32859911
AllCCS	[M+NH4]+	164.6	32859911
AllCCS	[M+Na]+	165.5	32859911
AllCCS	[M-H]-	161.0	32859911
AllCCS	[M+Na-2H]-	160.5	32859911
AllCCS	[M+HCOO]-	160.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-methylazathioprine	CN1C=NC(=C1[S+](C)C1=NC=NC2=C1N=CN2)N(=O)=O	2912.7	Standard polar	33892256
S-methylazathioprine	CN1C=NC(=C1[S+](C)C1=NC=NC2=C1N=CN2)N(=O)=O	2792.7	Standard non polar	33892256
S-methylazathioprine	CN1C=NC(=C1[S+](C)C1=NC=NC2=C1N=CN2)N(=O)=O	3136.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-methylazathioprine,1TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1[S+](C)C1=NC=NC2=C1N=CN2[Si](C)(C)C	2772.3	Semi standard non polar	33892256
S-methylazathioprine,1TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1[S+](C)C1=NC=NC2=C1N=CN2[Si](C)(C)C	2860.8	Standard non polar	33892256
S-methylazathioprine,1TMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1[S+](C)C1=NC=NC2=C1N=CN2[Si](C)(C)C	3648.4	Standard polar	33892256
S-methylazathioprine,1TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1[S+](C)C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C	2964.9	Semi standard non polar	33892256
S-methylazathioprine,1TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1[S+](C)C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C	3077.5	Standard non polar	33892256
S-methylazathioprine,1TBDMS,isomer #1	CN1C=NC([N+](=O)[O-])=C1[S+](C)C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C	3638.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-methylazathioprine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-7960000000-ade88b8d90b0a20b92d9	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-methylazathioprine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - S-methylazathioprine 10V, Positive-QTOF	splash10-0006-0090000000-8fa6c293469621ad44ee	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-methylazathioprine 20V, Positive-QTOF	splash10-0006-1090000000-78e733d1697f802e67e1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-methylazathioprine 40V, Positive-QTOF	splash10-0aou-9120000000-c8ea1587cf7e1487a283	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-methylazathioprine 10V, Positive-QTOF	splash10-0006-0090000000-7abeadd0d5658bf5109f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-methylazathioprine 20V, Positive-QTOF	splash10-014i-0930000000-1a0a4189e572a95a11c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-methylazathioprine 40V, Positive-QTOF	splash10-0ge9-1900000000-e859e34a990fda474a09	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131770020

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

Not Available

Showing metabocard for S-methylazathioprine (HMDB0061068)

MOL for HMDB0061068 (S-methylazathioprine)

3D MOL for HMDB0061068 (S-methylazathioprine)

3D SDF for HMDB0061068 (S-methylazathioprine)

3D-SDF for HMDB0061068 (S-methylazathioprine)

PDB for HMDB0061068 (S-methylazathioprine)

3D PDB for HMDB0061068 (S-methylazathioprine)

SMILES for HMDB0061068 (S-methylazathioprine)

INCHI for HMDB0061068 (S-methylazathioprine)

Structure for HMDB0061068 (S-methylazathioprine)

3D Structure for HMDB0061068 (S-methylazathioprine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra