Hmdb loader

Showing metabocard for Azathioprine (HMDB0015128)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:52 UTC
HMDB IDHMDB0015128
Secondary Accession Numbers
  • HMDB15128
Metabolite Identification
Common NameAzathioprine
DescriptionAzathioprine is only found in individuals that have used or taken this drug. It is an immunosuppressive pro-drug. It is converted into 6-mercaptopurine in the body where it blocks purine metabolism and DNA synthesis.Azathioprine antagonizes purine metabolism and may inhibit synthesis of DNA, RNA, and proteins. It may also interfere with cellular metabolism and inhibit mitosis. Its mechanism of action is likely due to incorporation of thiopurine analogues into the DNA structure, causing chain termination and cytotoxicity.
Structure
Data?1582753261
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015128 (Azathioprine)

993
  Mrv0541 02231215092D          

 19 21  0  0  0  0            999 V2000
    3.6703   -0.0585    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111    2.5335    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.2672    1.4716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021    0.0185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654   -1.0446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    1.3460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558   -1.2960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654   -2.3724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826    1.7266    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.6703   -2.5335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558    0.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -1.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703   -0.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    1.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -2.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0305   -0.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469   -1.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558   -2.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 13  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  2  0  0  0  0
  4 11  1  0  0  0  0
  4 15  1  0  0  0  0
  4 17  1  0  0  0  0
  5 12  1  0  0  0  0
  5 18  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  2  0  0  0  0
  7 13  2  0  0  0  0
  7 19  1  0  0  0  0
  8 16  1  0  0  0  0
  8 18  2  0  0  0  0
  9 14  1  0  0  0  0
 10 16  1  0  0  0  0
 10 19  2  0  0  0  0
 11 14  2  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
M  CHG  2   2  -1   9   1
M  END
Download

3D MOL for HMDB0015128 (Azathioprine)

HMDB0015128
     RDKit          3D
Azathioprine
 26 28  0  0  0  0  0  0  0  0999 V2000
   -2.0367    0.1164   -2.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4925    0.1835   -1.0518 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6358    0.7263   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018    0.5956    0.7441 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5918   -0.0399    1.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821   -0.3696    2.5373 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.6165   -1.3874    2.8407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    0.4514    3.5582 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.8559   -0.2846    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792   -1.1080    0.0152 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.0616    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8691    1.3761    0.2985 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9559    2.1842    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1978    1.6803    0.4117 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500    0.3660    0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5838   -0.3817    0.2603 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1946   -1.6618    0.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513   -1.7089    0.0689 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513   -0.4642    0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754   -0.9366   -2.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332    0.5871   -2.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7774    0.6264   -3.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3780    1.1969   -1.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369    3.2437    0.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -2.4867    0.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2399   -2.5660   -0.0365 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  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
  9  2  1  0
 19 11  1  0
 19 15  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
 13 24  1  0
 17 25  1  0
 18 26  1  0
M  CHG  2   6   1   8  -1
M  END
Download

3D SDF for HMDB0015128 (Azathioprine)

993
  Mrv0541 02231215092D          

 19 21  0  0  0  0            999 V2000
    3.6703   -0.0585    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111    2.5335    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.2672    1.4716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021    0.0185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654   -1.0446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    1.3460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558   -1.2960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654   -2.3724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826    1.7266    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.6703   -2.5335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558    0.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -1.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703   -0.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    1.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -2.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0305   -0.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469   -1.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558   -2.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 13  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  2  0  0  0  0
  4 11  1  0  0  0  0
  4 15  1  0  0  0  0
  4 17  1  0  0  0  0
  5 12  1  0  0  0  0
  5 18  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  2  0  0  0  0
  7 13  2  0  0  0  0
  7 19  1  0  0  0  0
  8 16  1  0  0  0  0
  8 18  2  0  0  0  0
  9 14  1  0  0  0  0
 10 16  1  0  0  0  0
 10 19  2  0  0  0  0
 11 14  2  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
M  CHG  2   2  -1   9   1
M  END
> <DATABASE_ID>
HMDB0015128

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)

> <INCHI_KEY>
LMEKQMALGUDUQG-UHFFFAOYSA-N

> <FORMULA>
C9H7N7O2S

> <MOLECULAR_WEIGHT>
277.263

> <EXACT_MASS>
277.038193193

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
24.258830779402988

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
1.1731439576666667

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.645114889803738

> <JCHEM_PKA_STRONGEST_BASIC>
4.003157356049786

> <JCHEM_POLAR_SURFACE_AREA>
118.10000000000001

> <JCHEM_REFRACTIVITY>
70.94619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azathioprine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0015128 (Azathioprine)

HMDB0015128
     RDKit          3D
Azathioprine
 26 28  0  0  0  0  0  0  0  0999 V2000
   -2.0367    0.1164   -2.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4925    0.1835   -1.0518 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6358    0.7263   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018    0.5956    0.7441 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5918   -0.0399    1.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821   -0.3696    2.5373 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.6165   -1.3874    2.8407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    0.4514    3.5582 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.8559   -0.2846    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792   -1.1080    0.0152 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.0616    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8691    1.3761    0.2985 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9559    2.1842    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1978    1.6803    0.4117 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500    0.3660    0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5838   -0.3817    0.2603 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1946   -1.6618    0.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513   -1.7089    0.0689 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513   -0.4642    0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754   -0.9366   -2.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332    0.5871   -2.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7774    0.6264   -3.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3780    1.1969   -1.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369    3.2437    0.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -2.4867    0.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2399   -2.5660   -0.0365 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  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
  9  2  1  0
 19 11  1  0
 19 15  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
 13 24  1  0
 17 25  1  0
 18 26  1  0
M  CHG  2   6   1   8  -1
M  END
Download

PDB for HMDB0015128 (Azathioprine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 993                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.851  -0.109   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       6.181   4.729   0.000  0.00  0.00           O-1
HETATM    3  O   UNK     0       7.965   2.747   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.111   0.035   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       9.642  -1.950   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       3.850   2.513   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.517  -2.419   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       9.642  -4.428   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       6.501   3.223   0.000  0.00  0.00           N+1
HETATM   10  N   UNK     0       6.851  -4.729   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.517   0.661   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.185  -2.419   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.851  -1.649   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.356   2.192   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   1.179   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.185  -3.959   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.790  -1.472   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.541  -3.189   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.517  -3.959   0.000  0.00  0.00           C+0
CONECT    1   11   13                                                       
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4   11   15   17                                                  
CONECT    5   12   18                                                       
CONECT    6   14   15                                                       
CONECT    7   13   19                                                       
CONECT    8   16   18                                                       
CONECT    9    2    3   14                                                  
CONECT   10   16   19                                                       
CONECT   11    1    4   14                                                  
CONECT   12    5   13   16                                                  
CONECT   13    1    7   12                                                  
CONECT   14    6    9   11                                                  
CONECT   15    4    6                                                       
CONECT   16    8   10   12                                                  
CONECT   17    4                                                            
CONECT   18    5    8                                                       
CONECT   19    7   10                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END
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3D PDB for HMDB0015128 (Azathioprine)

COMPND    HMDB0015128
HETATM    1  C1  UNL     1      -2.037   0.116  -2.443  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.492   0.184  -1.052  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.636   0.726  -0.595  1.00  0.00           C  
HETATM    4  N2  UNL     1      -3.702   0.596   0.744  1.00  0.00           N  
HETATM    5  C3  UNL     1      -2.592  -0.040   1.180  1.00  0.00           C  
HETATM    6  N3  UNL     1      -2.282  -0.370   2.537  1.00  0.00           N1+
HETATM    7  O1  UNL     1      -1.617  -1.387   2.841  1.00  0.00           O  
HETATM    8  O2  UNL     1      -2.724   0.451   3.558  1.00  0.00           O1-
HETATM    9  C4  UNL     1      -1.856  -0.285   0.038  1.00  0.00           C  
HETATM   10  S1  UNL     1      -0.279  -1.108   0.015  1.00  0.00           S  
HETATM   11  C5  UNL     1       1.058   0.062   0.177  1.00  0.00           C  
HETATM   12  N4  UNL     1       0.869   1.376   0.299  1.00  0.00           N  
HETATM   13  C6  UNL     1       1.956   2.184   0.416  1.00  0.00           C  
HETATM   14  N5  UNL     1       3.198   1.680   0.412  1.00  0.00           N  
HETATM   15  C7  UNL     1       3.450   0.366   0.293  1.00  0.00           C  
HETATM   16  N6  UNL     1       4.584  -0.382   0.260  1.00  0.00           N  
HETATM   17  C8  UNL     1       4.195  -1.662   0.122  1.00  0.00           C  
HETATM   18  N7  UNL     1       2.851  -1.709   0.069  1.00  0.00           N  
HETATM   19  C9  UNL     1       2.351  -0.464   0.172  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.975  -0.937  -2.798  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.033   0.587  -2.465  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.777   0.626  -3.067  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.378   1.197  -1.255  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.737   3.244   0.512  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.892  -2.487   0.066  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.240  -2.566  -0.036  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    9
CONECT    3    4    4   23
CONECT    4    5
CONECT    5    6    9    9
CONECT    6    7    7    8
CONECT    9   10
CONECT   10   11
CONECT   11   12   12   19
CONECT   12   13
CONECT   13   14   14   24
CONECT   14   15
CONECT   15   16   19   19
CONECT   16   17   17
CONECT   17   18   25
CONECT   18   19   26
END
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SMILES for HMDB0015128 (Azathioprine)

CN1C=NC(=C1SC1=NC=NC2=C1NC=N2)[N+]([O-])=O
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INCHI for HMDB0015128 (Azathioprine)

InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
6-((1-Methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purineChEBI
6-(1'-Methyl-4'-nitro-5'-imidazolyl)-mercaptopurineChEBI
ImuranChEBI
AzasanKegg
AzathioprinHMDB
AzatioprinHMDB
AzothioprineHMDB
Azathioprine sodium saltHMDB
Azathioprine sodiumHMDB
Azathioprine sulfateHMDB
ImmuranHMDB
ImurelHMDB
Sodium, azathioprineHMDB
Chemical FormulaC9H7N7O2S
Average Molecular Weight277.263
Monoisotopic Molecular Weight277.038193193
IUPAC Name6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine
Traditional Nameazathioprine
CAS Registry Number446-86-6
SMILES
CN1C=NC(=C1SC1=NC=NC2=C1NC=N2)[N+]([O-])=O
InChI Identifier
InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
InChI KeyLMEKQMALGUDUQG-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.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThioethers
Sub ClassAryl thioethers
Direct ParentDiarylthioethers
Alternative Parents
Substituents
  • Diarylthioether
  • 6-thiopurine
  • Imidazopyrimidine
  • Purine
  • Nitroaromatic compound
  • Nitroimidazole
  • N-substituted imidazole
  • Imidolactam
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • C-nitro compound
  • Organic nitro compound
  • Azacycle
  • Organic oxoazanium
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Sulfenyl compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point243.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.07 g/LNot Available
LogP0.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.07 g/LALOGPS
logP0.84ALOGPS
logP1.17ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)8.65ChemAxon
pKa (Strongest Basic)4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area118.1 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity70.95 m³·mol⁻¹ChemAxon
Polarizability24.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.29131661259
DarkChem[M-H]-160.74231661259
DeepCCS[M+H]+143.63230932474
DeepCCS[M-H]-140.7430932474
DeepCCS[M-2H]-175.62830932474
DeepCCS[M+Na]+151.61230932474
AllCCS[M+H]+159.532859911
AllCCS[M+H-H2O]+155.932859911
AllCCS[M+NH4]+162.832859911
AllCCS[M+Na]+163.832859911
AllCCS[M-H]-156.232859911
AllCCS[M+Na-2H]-155.632859911
AllCCS[M+HCOO]-155.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AzathioprineCN1C=NC(=C1SC1=NC=NC2=C1NC=N2)[N+]([O-])=O3021.2Standard polar33892256
AzathioprineCN1C=NC(=C1SC1=NC=NC2=C1NC=N2)[N+]([O-])=O2695.9Standard non polar33892256
AzathioprineCN1C=NC(=C1SC1=NC=NC2=C1NC=N2)[N+]([O-])=O3128.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Azathioprine,1TMS,isomer #1CN1C=NC([N+](=O)[O-])=C1SC1=NC=NC2=C1N([Si](C)(C)C)C=N22830.7Semi standard non polar33892256
Azathioprine,1TMS,isomer #1CN1C=NC([N+](=O)[O-])=C1SC1=NC=NC2=C1N([Si](C)(C)C)C=N22581.6Standard non polar33892256
Azathioprine,1TMS,isomer #1CN1C=NC([N+](=O)[O-])=C1SC1=NC=NC2=C1N([Si](C)(C)C)C=N24050.3Standard polar33892256
Azathioprine,1TBDMS,isomer #1CN1C=NC([N+](=O)[O-])=C1SC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N23011.8Semi standard non polar33892256
Azathioprine,1TBDMS,isomer #1CN1C=NC([N+](=O)[O-])=C1SC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N22796.0Standard non polar33892256
Azathioprine,1TBDMS,isomer #1CN1C=NC([N+](=O)[O-])=C1SC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N24021.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Azathioprine GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9680000000-14a922ede69208f7d93d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Azathioprine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine LC-ESI-qTof , Positive-QTOFsplash10-001l-2950000000-4d3fb67844876c2178142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine LC-ESI-qTof , Positive-QTOFsplash10-000x-0950000000-b6de6073310270167ffb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine LC-ESI-QFT , negative-QTOFsplash10-004i-0390000000-0d11d23373539cfb283c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine , positive-QTOFsplash10-000x-0950000000-b6de6073310270167ffb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine , positive-QTOFsplash10-001l-2950000000-4d3fb67844876c2178142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 35V, Negative-QTOFsplash10-004i-0390000000-58368875ea6ed88ee61c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 15V, Negative-QTOFsplash10-004i-0090000000-21d13daccc3ca63118292021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 30V, Negative-QTOFsplash10-004i-0590000000-b73f9f2e26259b004f752021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 90V, Positive-QTOFsplash10-01b9-7900000000-b14a64aca199c8b71caf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 75V, Positive-QTOFsplash10-0gir-6910000000-5e2cea2a00375e82d2942021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 15V, Positive-QTOFsplash10-0006-0950000000-dd45895b2d199860f1572021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 30V, Positive-QTOFsplash10-000x-2950000000-f4883419404f23b8f2a12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 60V, Positive-QTOFsplash10-0gir-5920000000-c941e300fe4d1869fd8e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 45V, Positive-QTOFsplash10-00lv-4930000000-c315bdc3abb371f4e4262021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 60V, Positive-QTOFsplash10-0gir-5920000000-3d187b69fbd90dc9b4de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 90V, Positive-QTOFsplash10-01b9-7900000000-c328e8adab736ddf28192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 60V, Negative-QTOFsplash10-0a4i-0900000000-b07a1492f0de60ac50ce2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 90V, Negative-QTOFsplash10-07vl-4900000000-3773c3f34878b3d9eef82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Azathioprine 75V, Negative-QTOFsplash10-0aor-2900000000-aa84765db89a7c5cac3d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azathioprine 10V, Positive-QTOFsplash10-004i-0090000000-127672e50f7d85ca73022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azathioprine 20V, Positive-QTOFsplash10-05i0-0090000000-7bb3b92e927e16854e1d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azathioprine 40V, Positive-QTOFsplash10-0a4i-9120000000-e50a6491ae4f28b8eeb02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azathioprine 10V, Negative-QTOFsplash10-004i-3090000000-df6cb72af7b792b5cdfb2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azathioprine 20V, Negative-QTOFsplash10-004i-2490000000-b8ce493eef32ac50f4582016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azathioprine 40V, Negative-QTOFsplash10-00ba-5910000000-2134d4c288ab79f6a6892016-08-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00993 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00993 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00993
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2178
KEGG Compound IDC06837
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAzathioprine
METLIN IDNot Available
PubChem Compound2265
PDB IDNot Available
ChEBI ID2948
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Woodroffe R, Yao GL, Meads C, Bayliss S, Ready A, Raftery J, Taylor RS: Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study. Health Technol Assess. 2005 May;9(21):1-179, iii-iv. [PubMed:15899149 ]
  2. Gombar VK, Enslein K, Blake BW: Carcinogenicity of azathioprine: an S-AR investigation. Mutat Res. 1993 May;302(1):7-12. [PubMed:7683109 ]
  3. Konstantopoulou M, Belgi A, Griffiths KD, Seale JR, Macfarlane AW: Azathioprine-induced pancytopenia in a patient with pompholyx and deficiency of erythrocyte thiopurine methyltransferase. BMJ. 2005 Feb 12;330(7487):350-1. [PubMed:15705694 ]

Enzymes

Enzyme Details
1. Xanthine dehydrogenase/oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
References
  1. Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]
Enzyme Details
2. Thiopurine S-methyltransferase
General function:
Involved in thiopurine S-methyltransferase activity
Specific function:
Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
Gene Name:
TPMT
Uniprot ID:
P51580
Molecular weight:
28180.09
References
  1. Sahasranaman S, Howard D, Roy S: Clinical pharmacology and pharmacogenetics of thiopurines. Eur J Clin Pharmacol. 2008 Aug;64(8):753-67. doi: 10.1007/s00228-008-0478-6. Epub 2008 May 28. [PubMed:18506437 ]
Enzyme Details
3. Hypoxanthine-guanine phosphoribosyltransferase
General function:
Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:
HPRT1
Uniprot ID:
P00492
Molecular weight:
24579.155
References
  1. Anstey A, Lear JT: Azathioprine: clinical pharmacology and current indications in autoimmune disorders. BioDrugs. 1998 Jan;9(1):33-47. [PubMed:18020555 ]
  2. Dubinsky MC: Azathioprine, 6-mercaptopurine in inflammatory bowel disease: pharmacology, efficacy, and safety. Clin Gastroenterol Hepatol. 2004 Sep;2(9):731-43. [PubMed:15354273 ]