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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014416

Secondary Accession Numbers

HMDB14416

Metabolite Identification

Common Name

Diatrizoate

Description

Diatrizoate is only found in individuals that have used or taken this drug. It is a commonly used x-ray contrast medium. As diatrizoate meglumine and as Diatrizoate sodium, it is used for gastrointestinal studies, angiography, and urography. [PubChem]Diatrizoate is an iodine-containing X-ray contrast agent. Iodated contrast agents were among the first contrast agents developed. Iodine is known to be particular electron-dense and to effectively scatter or stop X-rays. A good contrast agent requires a high density of electron-dense atoms. Therefore, the more iodine, the more "dense" the x-ray effect. Iodine based contrast media are water soluble and harmless to the body. These contrast agents are sold as clear colorless water solutions, the concentration is usually expressed as mg I/ml. Modern iodinated contrast agents can be used almost anywhere in the body. Most often they are used intravenously, but for various purposes they can also be used intraarterially, intrathecally (the spine) and intraabdominally - just about any body cavity or potential space.

Structure

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

HMDB0014416
     RDKit          3D
Diatrizoate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -4.4434   -1.8883   -0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -1.2566    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7687   -1.3943    1.2694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250   -0.5144   -0.8217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1896    0.1224   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0369   -0.4828   -0.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1034   -2.4590   -1.3598 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.2255    0.1465   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4569   -0.5615   -0.5193 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -1.3391    0.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3347   -2.0354    0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.4591    1.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1757    1.4439    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871    2.3954    0.5853 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0343    2.0952    0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625    3.4685    0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1420    3.6656    2.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049    4.5389   -0.0769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104    1.4198   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193    2.4315    0.2053 I   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5200   -2.9426    0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5446   -1.9100   -1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3340   -1.3149    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7989   -0.4196   -1.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8943   -0.4593   -1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973   -2.7176   -0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7408   -2.5326    1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0963   -1.2457   -0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312    5.2052   -0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  8 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  2  0
 19 20  1  0
 19  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 18 29  1  0
M  END

2140
  Mrv0541 02231214332D          

 20 20  0  0  0  0            999 V2000
    2.3645    0.4125    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4125    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0625    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 14  1  0  0  0  0
  3 15  1  0  0  0  0
  4 16  1  0  0  0  0
  5 16  2  0  0  0  0
  6 17  2  0  0  0  0
  7 18  2  0  0  0  0
  8 10  1  0  0  0  0
  8 17  1  0  0  0  0
  9 11  1  0  0  0  0
  9 18  1  0  0  0  0
 10 12  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014416

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I

> <INCHI_IDENTIFIER>
InChI=1S/C11H9I3N2O4/c1-3(17)15-9-6(12)5(11(19)20)7(13)10(8(9)14)16-4(2)18/h1-2H3,(H,15,17)(H,16,18)(H,19,20)

> <INCHI_KEY>
YVPYQUNUQOZFHG-UHFFFAOYSA-N

> <FORMULA>
C11H9I3N2O4

> <MOLECULAR_WEIGHT>
613.9136

> <EXACT_MASS>
613.769637046

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.428271697292196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5-diacetamido-2,4,6-triiodobenzoic acid

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.8930828936666666

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.841682571367873

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1676699700991264

> <JCHEM_PKA_STRONGEST_BASIC>
-4.240460823875686

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
103.12769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diatrizoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014416
     RDKit          3D
Diatrizoate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -4.4434   -1.8883   -0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -1.2566    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7687   -1.3943    1.2694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250   -0.5144   -0.8217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1896    0.1224   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0369   -0.4828   -0.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1034   -2.4590   -1.3598 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.2255    0.1465   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4569   -0.5615   -0.5193 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -1.3391    0.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3347   -2.0354    0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.4591    1.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1757    1.4439    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871    2.3954    0.5853 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0343    2.0952    0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625    3.4685    0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1420    3.6656    2.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049    4.5389   -0.0769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104    1.4198   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193    2.4315    0.2053 I   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5200   -2.9426    0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5446   -1.9100   -1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3340   -1.3149    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7989   -0.4196   -1.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8943   -0.4593   -1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973   -2.7176   -0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7408   -2.5326    1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0963   -1.2457   -0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312    5.2052   -0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  8 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  2  0
 19 20  1  0
 19  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 18 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2140                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  I   UNK     0       4.414   0.770   0.000  0.00  0.00           I+0
HETATM    2  I   UNK     0       9.748   0.770   0.000  0.00  0.00           I+0
HETATM    3  I   UNK     0       7.081  -3.850   0.000  0.00  0.00           I+0
HETATM    4  O   UNK     0       9.748  -3.850   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.082  -1.540   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.747  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.748   2.310   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       4.414  -2.310   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       7.081   2.310   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   4.620   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5   16                                                            
CONECT    6   17                                                            
CONECT    7   18                                                            
CONECT    8   10   17                                                       
CONECT    9   11   18                                                       
CONECT   10    8   12   15                                                  
CONECT   11    9   12   14                                                  
CONECT   12    1   10   11                                                  
CONECT   13   14   15   16                                                  
CONECT   14    2   11   13                                                  
CONECT   15    3   10   13                                                  
CONECT   16    4    5   13                                                  
CONECT   17    6    8   19                                                  
CONECT   18    7    9   20                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0014416
HETATM    1  C1  UNL     1      -4.443  -1.888  -0.297  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.172  -1.257   0.096  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.769  -1.394   1.269  1.00  0.00           O  
HETATM    4  N1  UNL     1      -2.425  -0.514  -0.822  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.190   0.122  -0.510  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.037  -0.483  -0.649  1.00  0.00           C  
HETATM    7  I1  UNL     1       0.103  -2.459  -1.360  1.00  0.00           I  
HETATM    8  C5  UNL     1       1.226   0.147  -0.344  1.00  0.00           C  
HETATM    9  N2  UNL     1       2.457  -0.562  -0.519  1.00  0.00           N  
HETATM   10  C6  UNL     1       3.060  -1.339   0.464  1.00  0.00           C  
HETATM   11  C7  UNL     1       4.335  -2.035   0.190  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.530  -1.459   1.592  1.00  0.00           O  
HETATM   13  C8  UNL     1       1.176   1.444   0.122  1.00  0.00           C  
HETATM   14  I2  UNL     1       2.987   2.395   0.585  1.00  0.00           I  
HETATM   15  C9  UNL     1      -0.034   2.095   0.279  1.00  0.00           C  
HETATM   16  C10 UNL     1      -0.063   3.469   0.774  1.00  0.00           C  
HETATM   17  O3  UNL     1      -0.142   3.666   2.015  1.00  0.00           O  
HETATM   18  O4  UNL     1      -0.005   4.539  -0.077  1.00  0.00           O  
HETATM   19  C11 UNL     1      -1.210   1.420  -0.042  1.00  0.00           C  
HETATM   20  I3  UNL     1      -3.019   2.431   0.205  1.00  0.00           I  
HETATM   21  H1  UNL     1      -4.520  -2.943   0.073  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.545  -1.910  -1.408  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.334  -1.315   0.074  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.799  -0.420  -1.807  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.894  -0.459  -1.459  1.00  0.00           H  
HETATM   26  H6  UNL     1       4.297  -2.718  -0.668  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.741  -2.533   1.112  1.00  0.00           H  
HETATM   28  H8  UNL     1       5.096  -1.246  -0.077  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.731   5.205  -0.001  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3    4
CONECT    4    5   24
CONECT    5    6    6   19
CONECT    6    7    8
CONECT    8    9   13   13
CONECT    9   10   25
CONECT   10   11   12   12
CONECT   11   26   27   28
CONECT   13   14   15
CONECT   15   16   19   19
CONECT   16   17   17   18
CONECT   18   29
CONECT   19   20
END

HMDB0014416
     RDKit          3D
Diatrizoate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -4.4434   -1.8883   -0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -1.2566    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7687   -1.3943    1.2694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250   -0.5144   -0.8217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1896    0.1224   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0369   -0.4828   -0.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1034   -2.4590   -1.3598 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.2255    0.1465   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4569   -0.5615   -0.5193 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -1.3391    0.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3347   -2.0354    0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.4591    1.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1757    1.4439    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871    2.3954    0.5853 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0343    2.0952    0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625    3.4685    0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1420    3.6656    2.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0049    4.5389   -0.0769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104    1.4198   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193    2.4315    0.2053 I   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5200   -2.9426    0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5446   -1.9100   -1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3340   -1.3149    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7989   -0.4196   -1.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8943   -0.4593   -1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973   -2.7176   -0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7408   -2.5326    1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0963   -1.2457   -0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312    5.2052   -0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  8 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  2  0
 19 20  1  0
 19  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 18 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,4,6-Triiodo-3,5-diacetamidobenzoic acid	ChEBI
3,5-Bis(acetylamino)-2,4,6-triiodobenzoic acid	ChEBI
Acide amidotrizoique	ChEBI
Acidum amidotrizoicum	ChEBI
Acidum diacetylaminotrijodbenzoicum	ChEBI
Amidotrizoate	ChEBI
Amidotrizoic acid (anhydrous)	ChEBI
Diatrizoesaure	ChEBI
Diatrizoic acid	ChEBI
Diatrizoic acid (anhydrous)	ChEBI
Methalamic acid	ChEBI
Triombrin	ChEBI
Urografin acid	ChEBI
Urogranoic acid	ChEBI
Amidotrizoic acid	Kegg
2,4,6-Triiodo-3,5-diacetamidobenzoate	Generator
3,5-Bis(acetylamino)-2,4,6-triiodobenzoate	Generator
Amidotrizoate (anhydrous)	Generator
Diatrizoate (anhydrous)	Generator
Methalamate	Generator
Urogranoate	Generator
Diatriazoate	HMDB
Diatrizoate sodium salt	HMDB
Diatrizoic acid sodium salt	HMDB
Sodium amidotrizoate	HMDB
Sodium diatrizoate	HMDB
Amidotrezoate	HMDB
Diatrizoate, sodium-magnesium	HMDB
Urothrast	HMDB
Urotrast	HMDB
Hypaque	HMDB
Diatrizoate sodium	HMDB
Diatrizoate, sodium	HMDB
Hypaque 50	HMDB
Sodium-magnesium diatrizoate	HMDB
Diatrizoate	ChEBI

Chemical Formula

C₁₁H₉I₃N₂O₄

Average Molecular Weight

613.9136

Monoisotopic Molecular Weight

613.769637046

IUPAC Name

3,5-diacetamido-2,4,6-triiodobenzoic acid

Traditional Name

diatrizoate

CAS Registry Number

117-96-4

SMILES

CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I

InChI Identifier

InChI=1S/C11H9I3N2O4/c1-3(17)15-9-6(12)5(11(19)20)7(13)10(8(9)14)16-4(2)18/h1-2H3,(H,15,17)(H,16,18)(H,19,20)

InChI Key

YVPYQUNUQOZFHG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Halobenzoic acids

Alternative Parents

Substituents

Halobenzoic acid
4-halobenzoic acid
2-halobenzoic acid
4-halobenzoic acid or derivatives
2-halobenzoic acid or derivatives
Benzoic acid
Benzoyl
1-carboxy-2-haloaromatic compound
Halobenzene
Iodobenzene
Aryl halide
Aryl iodide
Vinylogous halide
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic oxide
Organohalogen compound
Organoiodide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organoiodine compound (CHEBI:53691 )
acetamides (CHEBI:53691 )
benzoic acids (CHEBI:53691 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014416)

Source

Exogenous

Exogenous (HMDB: HMDB0014416)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.11 g/L	Not Available
LogP	3.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.27	ALOGPS
logP	2.89	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.17	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.5 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	103.13 m³·mol⁻¹	ChemAxon
Polarizability	38.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	191.828	30932474
DeepCCS	[M-H]-	189.124	30932474
DeepCCS	[M-2H]-	223.887	30932474
DeepCCS	[M+Na]+	199.627	30932474
AllCCS	[M+H]+	194.1	32859911
AllCCS	[M+H-H2O]+	192.5	32859911
AllCCS	[M+NH4]+	195.5	32859911
AllCCS	[M+Na]+	195.9	32859911
AllCCS	[M-H]-	194.8	32859911
AllCCS	[M+Na-2H]-	196.6	32859911
AllCCS	[M+HCOO]-	198.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.26 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8558 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.52 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	721.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	310.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	41.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	68.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	289.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	368.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	524.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	633.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	72.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	887.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	218.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	628.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	529.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	512.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diatrizoate	CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I	4183.2	Standard polar	33892256
Diatrizoate	CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I	3103.5	Standard non polar	33892256
Diatrizoate	CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I	3544.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diatrizoate,1TMS,isomer #1	CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(=O)O[Si](C)(C)C)=C1I	3059.3	Semi standard non polar	33892256
Diatrizoate,1TMS,isomer #2	CC(=O)NC1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I	2854.4	Semi standard non polar	33892256
Diatrizoate,2TMS,isomer #1	CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I	2981.4	Semi standard non polar	33892256
Diatrizoate,2TMS,isomer #1	CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I	2773.0	Standard non polar	33892256
Diatrizoate,2TMS,isomer #1	CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I	3278.4	Standard polar	33892256
Diatrizoate,2TMS,isomer #2	CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C	2769.6	Semi standard non polar	33892256
Diatrizoate,2TMS,isomer #2	CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C	2859.4	Standard non polar	33892256
Diatrizoate,2TMS,isomer #2	CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C	2803.6	Standard polar	33892256
Diatrizoate,3TMS,isomer #1	CC(=O)N(C1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C	2901.2	Semi standard non polar	33892256
Diatrizoate,3TMS,isomer #1	CC(=O)N(C1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C	2881.7	Standard non polar	33892256
Diatrizoate,3TMS,isomer #1	CC(=O)N(C1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I)[Si](C)(C)C	2607.9	Standard polar	33892256
Diatrizoate,1TBDMS,isomer #1	CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1I	3338.5	Semi standard non polar	33892256
Diatrizoate,1TBDMS,isomer #2	CC(=O)NC1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I	3117.8	Semi standard non polar	33892256
Diatrizoate,2TBDMS,isomer #1	CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I	3477.7	Semi standard non polar	33892256
Diatrizoate,2TBDMS,isomer #1	CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I	3184.6	Standard non polar	33892256
Diatrizoate,2TBDMS,isomer #1	CC(=O)NC1=C(I)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I	3335.5	Standard polar	33892256
Diatrizoate,2TBDMS,isomer #2	CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I)[Si](C)(C)C(C)(C)C	3224.9	Semi standard non polar	33892256
Diatrizoate,2TBDMS,isomer #2	CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I)[Si](C)(C)C(C)(C)C	3240.3	Standard non polar	33892256
Diatrizoate,2TBDMS,isomer #2	CC(=O)N(C1=C(I)C(C(=O)O)=C(I)C(N(C(C)=O)[Si](C)(C)C(C)(C)C)=C1I)[Si](C)(C)C(C)(C)C	2999.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Diatrizoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-2000190000-1e1a0180629c7b977520	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diatrizoate GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-7000049000-3612e2236d7d0fb6b1f7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diatrizoate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diatrizoate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diatrizoate GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diatrizoate GC-MS ("Diatrizoate,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-11-02	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-QFT , negative-QTOF	splash10-03di-0900000000-99b8784c2130ad614260	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-03di-0009000000-41980f595b357f23008b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-03di-0009000000-1577dcdfa6ca41fd47b9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-03e9-0069000000-8d549556fd92c5af8607	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-001i-0291000000-fff2719e16023b6214af	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-001i-0980000000-babd1700c93e5136416d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-000t-0930000000-b28e85bca3033f358799	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-052b-1920000000-d7d537885b4316f3992e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-03di-0009000000-8d1e15522e91dc9d3243	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-03e9-0069000000-e6815d5eef85411e6e7d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-001i-0291000000-2032e83ba9286860a6dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-001i-0980000000-f7868434c5092c43628f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-000t-0930000000-285b756b15a887efa1b6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-052e-0920000000-29b6aab602522eee1d69	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate LC-ESI-ITFT , positive-QTOF	splash10-03di-0009000000-cf3196e4c8cdf6f33e07	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate 45V, Positive-QTOF	splash10-001i-0291000000-8df60ae70ca6442cef17	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate 35V, Positive-QTOF	splash10-03di-0009000000-41980f595b357f23008b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate 15V, Positive-QTOF	splash10-03di-0009000000-87773465a95c7c9582c9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diatrizoate 15V, Positive-QTOF	splash10-03di-0009000000-1577dcdfa6ca41fd47b9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diatrizoate 10V, Positive-QTOF	splash10-03di-0000029000-d1432154fa0a600981e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diatrizoate 20V, Positive-QTOF	splash10-03k9-0000097000-8609063f82dfe7f94b03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diatrizoate 40V, Positive-QTOF	splash10-0udi-1000090000-f972ccbdaf519374a553	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diatrizoate 10V, Negative-QTOF	splash10-03xr-0000095000-f0aa688e5108b5fe4104	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diatrizoate 20V, Negative-QTOF	splash10-0229-0000094000-2f05e7ee617ec0d72113	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diatrizoate 40V, Negative-QTOF	splash10-0udi-1000090000-986a25c2de253dd053a1	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB00271	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00271	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00271

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2055

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diatrizoic_acid

METLIN ID

Not Available

PubChem Compound

2140

PDB ID

Not Available

ChEBI ID

53691

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 Diatrizoate (HMDB0014416)

MOL for HMDB0014416 (Diatrizoate)

3D MOL for HMDB0014416 (Diatrizoate)

3D SDF for HMDB0014416 (Diatrizoate)

3D-SDF for HMDB0014416 (Diatrizoate)

PDB for HMDB0014416 (Diatrizoate)

3D PDB for HMDB0014416 (Diatrizoate)

SMILES for HMDB0014416 (Diatrizoate)

INCHI for HMDB0014416 (Diatrizoate)

Structure for HMDB0014416 (Diatrizoate)

3D Structure for HMDB0014416 (Diatrizoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra