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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:04:26 UTC

Update Date

2021-09-26 23:08:50 UTC

HMDB ID

HMDB0254687

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Metrizoic acid

Description

Metrizoic acid, also known as acide metrizoique or metrizoate, belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. Metrizoic acid is a drug which is used for use as a contrast medium [l1597]. Metrizoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Metrizoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Metrizoic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254687
     RDKit          3D
Metrizoic acid
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.4891   -1.2892    1.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -1.1934   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -1.8303   -0.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -0.5116   -0.2091 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659    0.1859   -0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894    1.5506   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702    2.6908   -0.7987 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.1650    2.1719   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    3.6137   -0.8310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011    4.1273   -0.8758 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438    4.4116   -0.9916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755    1.4088   -0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8756    2.3248   -0.5079 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9673    0.0464   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -0.7165   -0.0422 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670   -1.3746   -1.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7827   -0.8184    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0144   -1.6266    1.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912   -0.2126    2.1877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -0.5383   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390   -2.6274    0.1903 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.0671   -0.5834    1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731   -1.0920    1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -2.3098    1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5043   -0.7772   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4318    5.0195   -0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736   -2.2667   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212   -1.6410   -1.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5571   -0.6361   -2.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7626   -1.4874    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7774   -2.7203    1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4894   -1.2986    2.3559 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  2  0
  9 11  1  0
  8 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 14 20  2  0
 20 21  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 11 26  1  0
 16 27  1  0
 16 28  1  0
 16 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
M  END


  Mrv1572011271516082D          

 21 21  0  0  0  0            999 V2000
    0.0000    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.6187    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.8562    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.6187    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3 12  1  0  0  0  0
  3  2  1  0  0  0  0
  2 15  1  0  0  0  0
  5  7  1  0  0  0  0
  5  6  2  0  0  0  0
  6  8  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  2  0  0  0  0
  4  9  1  0  0  0  0
  6  1  1  0  0  0  0
  1  2  2  0  0  0  0
  1 11  1  0  0  0  0
  7 10  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 16  1  0  0  0  0
 11 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  7 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254687

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C(C)=O)C1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I

> <INCHI_IDENTIFIER>
InChI=1S/C12H11I3N2O4/c1-4(18)16-10-7(13)6(12(20)21)8(14)11(9(10)15)17(3)5(2)19/h1-3H3,(H,16,18)(H,20,21)

> <INCHI_KEY>
GGGDNPWHMNJRFN-UHFFFAOYSA-N

> <FORMULA>
C12H11I3N2O4

> <MOLECULAR_WEIGHT>
627.943

> <EXACT_MASS>
627.78529

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
39.933347222846706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)benzoic acid

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
2.7571489623333334

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.13898438173849

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.163155274865334

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8989699821147625

> <JCHEM_POLAR_SURFACE_AREA>
86.71000000000001

> <JCHEM_REFRACTIVITY>
106.24359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metrizoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254687
     RDKit          3D
Metrizoic acid
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.4891   -1.2892    1.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -1.1934   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -1.8303   -0.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -0.5116   -0.2091 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659    0.1859   -0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894    1.5506   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702    2.6908   -0.7987 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.1650    2.1719   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    3.6137   -0.8310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011    4.1273   -0.8758 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438    4.4116   -0.9916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755    1.4088   -0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8756    2.3248   -0.5079 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9673    0.0464   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -0.7165   -0.0422 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670   -1.3746   -1.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7827   -0.8184    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0144   -1.6266    1.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912   -0.2126    2.1877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -0.5383   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390   -2.6274    0.1903 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.0671   -0.5834    1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731   -1.0920    1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -2.3098    1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5043   -0.7772   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4318    5.0195   -0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736   -2.2667   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212   -1.6410   -1.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5571   -0.6361   -2.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7626   -1.4874    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7774   -2.7203    1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4894   -1.2986    2.3559 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  2  0
  9 11  1  0
  8 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 14 20  2  0
 20 21  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 11 26  1  0
 16 27  1  0
 16 28  1  0
 16 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 27-NOV-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-NOV-15         0                                  
HETATM    1  C   UNK     0       0.000   1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.385   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.667  -1.925   0.000  0.00  0.00           N+0
HETATM    8  I   UNK     0      -2.667   1.155   0.000  0.00  0.00           I+0
HETATM    9  I   UNK     0       0.000  -3.465   0.000  0.00  0.00           I+0
HETATM   10  C   UNK     0      -4.001  -1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   2.695   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.667  -1.925   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -5.335  -1.925   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001   0.385   0.000  0.00  0.00           O+0
HETATM   15  I   UNK     0       2.667   1.155   0.000  0.00  0.00           I+0
HETATM   16  O   UNK     0       1.334   3.465   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334   3.465   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -1.155   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001   0.385   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  -1.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -3.465   0.000  0.00  0.00           C+0
CONECT    1    6    2   11                                                  
CONECT    2    3   15    1                                                  
CONECT    3   12    2    4                                                  
CONECT    4    5    3    9                                                  
CONECT    5    7    6    4                                                  
CONECT    6    5    8    1                                                  
CONECT    7    5   10   21                                                  
CONECT    8    6                                                            
CONECT    9    4                                                            
CONECT   10    7   13   14                                                  
CONECT   11    1   16   17                                                  
CONECT   12    3   18                                                       
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15    2                                                            
CONECT   16   11                                                            
CONECT   17   11                                                            
CONECT   18   12   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    7                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0254687
HETATM    1  C1  UNL     1       4.489  -1.289   1.252  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.759  -1.193  -0.106  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.400  -1.830  -0.997  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.626  -0.512  -0.209  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.466   0.186  -0.315  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.389   1.551  -0.548  1.00  0.00           C  
HETATM    7  I1  UNL     1       3.170   2.691  -0.799  1.00  0.00           I  
HETATM    8  C5  UNL     1       0.165   2.172  -0.607  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.041   3.614  -0.831  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.101   4.127  -0.876  1.00  0.00           O  
HETATM   11  O3  UNL     1       1.144   4.412  -0.992  1.00  0.00           O  
HETATM   12  C7  UNL     1      -0.976   1.409  -0.431  1.00  0.00           C  
HETATM   13  I2  UNL     1      -2.876   2.325  -0.508  1.00  0.00           I  
HETATM   14  C8  UNL     1      -0.967   0.046  -0.199  1.00  0.00           C  
HETATM   15  N2  UNL     1      -2.156  -0.717  -0.042  1.00  0.00           N  
HETATM   16  C9  UNL     1      -2.667  -1.375  -1.237  1.00  0.00           C  
HETATM   17  C10 UNL     1      -2.783  -0.818   1.215  1.00  0.00           C  
HETATM   18  C11 UNL     1      -4.014  -1.627   1.411  1.00  0.00           C  
HETATM   19  O4  UNL     1      -2.291  -0.213   2.188  1.00  0.00           O  
HETATM   20  C12 UNL     1       0.273  -0.538  -0.145  1.00  0.00           C  
HETATM   21  I3  UNL     1       0.339  -2.627   0.190  1.00  0.00           I  
HETATM   22  H1  UNL     1       4.067  -0.583   1.963  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.573  -1.092   1.084  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.374  -2.310   1.641  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.504  -0.777  -1.570  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.432   5.019  -0.227  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.074  -2.267  -1.517  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.721  -1.641  -1.151  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.557  -0.636  -2.089  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.763  -1.487   0.585  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.777  -2.720   1.509  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.489  -1.299   2.356  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5   25
CONECT    5    6    6   20
CONECT    6    7    8
CONECT    8    9   12   12
CONECT    9   10   10   11
CONECT   11   26
CONECT   12   13   14
CONECT   14   15   20   20
CONECT   15   16   17
CONECT   16   27   28   29
CONECT   17   18   19   19
CONECT   18   30   31   32
CONECT   20   21
END

HMDB0254687
     RDKit          3D
Metrizoic acid
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.4891   -1.2892    1.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -1.1934   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -1.8303   -0.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -0.5116   -0.2091 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659    0.1859   -0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3894    1.5506   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702    2.6908   -0.7987 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.1650    2.1719   -0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    3.6137   -0.8310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011    4.1273   -0.8758 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438    4.4116   -0.9916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755    1.4088   -0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8756    2.3248   -0.5079 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9673    0.0464   -0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -0.7165   -0.0422 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670   -1.3746   -1.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7827   -0.8184    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0144   -1.6266    1.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912   -0.2126    2.1877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -0.5383   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390   -2.6274    0.1903 I   0  0  0  0  0  0  0  0  0  0  0  0
    4.0671   -0.5834    1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731   -1.0920    1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -2.3098    1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5043   -0.7772   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4318    5.0195   -0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736   -2.2667   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212   -1.6410   -1.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5571   -0.6361   -2.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7626   -1.4874    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7774   -2.7203    1.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4894   -1.2986    2.3559 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  2  0
  9 11  1  0
  8 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 14 20  2  0
 20 21  1  0
 20  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 11 26  1  0
 16 27  1  0
 16 28  1  0
 16 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(Acetylamino)-5-(acetylmethylamino)-2,4,6-triiodobenzoic acid	ChEBI
3-Acetamido-2,4,6-triiodo-5-(N-methylacetamido)benzoic acid	ChEBI
3-Acetamido-2,4,6-triiodo-5-N-methylacetamidobenzoic acid	ChEBI
Acide metrizoique	ChEBI
Acidum metrizoicum	ChEBI
3-(Acetylamino)-5-(acetylmethylamino)-2,4,6-triiodobenzoate	Generator
3-Acetamido-2,4,6-triiodo-5-(N-methylacetamido)benzoate	Generator
3-Acetamido-2,4,6-triiodo-5-N-methylacetamidobenzoate	Generator
Metrizoate	Generator
Metrizoate sodium	MeSH
Sodium, metrizoate	MeSH
Triosil	MeSH
Isopaque	MeSH

Chemical Formula

C₁₂H₁₁I₃N₂O₄

Average Molecular Weight

627.943

Monoisotopic Molecular Weight

627.78529

IUPAC Name

3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)benzoic acid

Traditional Name

metrizoic acid

CAS Registry Number

Not Available

SMILES

CN(C(C)=O)C1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I

InChI Identifier

InChI=1S/C12H11I3N2O4/c1-4(18)16-10-7(13)6(12(20)21)8(14)11(9(10)15)17(3)5(2)19/h1-3H3,(H,16,18)(H,20,21)

InChI Key

GGGDNPWHMNJRFN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylaminobenzoic acid and derivatives

Alternative Parents

Substituents

Acylaminobenzoic acid or derivatives
O-haloacetanilide
P-haloacetanilide
Haloacetanilide
Acetanilide
2-halobenzoic acid
4-halobenzoic acid
Halobenzoic acid
Halobenzoic acid or derivatives
2-halobenzoic acid or derivatives
4-halobenzoic acid or derivatives
Benzoic acid
N-acetylarylamine
Anilide
N-arylamide
1-carboxy-2-haloaromatic compound
Benzoyl
Halobenzene
Iodobenzene
Aryl halide
Aryl iodide
Vinylogous halide
Acetamide
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organic nitrogen compound
Organohalogen compound
Organoiodide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:34847 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0254687)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.18	ALOGPS
logP	2.76	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.16	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.71 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.24 m³·mol⁻¹	ChemAxon
Polarizability	39.93 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]+	195.233	30932474
DeepCCS	[M-H]-	192.689	30932474
DeepCCS	[M-2H]-	227.292	30932474
DeepCCS	[M+Na]+	202.644	30932474
AllCCS	[M+H]+	195.9	32859911
AllCCS	[M+H-H2O]+	194.4	32859911
AllCCS	[M+NH4]+	197.2	32859911
AllCCS	[M+Na]+	197.5	32859911
AllCCS	[M-H]-	202.3	32859911
AllCCS	[M+Na-2H]-	204.2	32859911
AllCCS	[M+HCOO]-	206.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.6844 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.5 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	852.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	270.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	62.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	269.5 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	406.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	294.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	637.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	141.1 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	1002.3 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	202.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	547.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	455.5 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	422.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Metrizoic acid	CN(C(C)=O)C1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I	4304.4	Standard polar	33892256
Metrizoic acid	CN(C(C)=O)C1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I	2961.6	Standard non polar	33892256
Metrizoic acid	CN(C(C)=O)C1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I	3484.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Metrizoic acid,2TMS,isomer #1	CC(=O)N(C)C1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I	2900.1	Semi standard non polar	33892256
Metrizoic acid,2TMS,isomer #1	CC(=O)N(C)C1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I	2853.3	Standard non polar	33892256
Metrizoic acid,2TMS,isomer #1	CC(=O)N(C)C1=C(I)C(C(=O)O[Si](C)(C)C)=C(I)C(N(C(C)=O)[Si](C)(C)C)=C1I	2756.9	Standard polar	33892256
Metrizoic acid,2TBDMS,isomer #1	CC(=O)N(C)C1=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	3368.2	Semi standard non polar	33892256
Metrizoic acid,2TBDMS,isomer #1	CC(=O)N(C)C1=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	3282.2	Standard non polar	33892256
Metrizoic acid,2TBDMS,isomer #1	CC(=O)N(C)C1=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	3004.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Metrizoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-1000090000-768dbd3cc43adb825806	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metrizoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metrizoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metrizoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metrizoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Metrizoic acid 10V, Positive-QTOF	splash10-004i-0000049000-fd870300d62e0810dde6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metrizoic acid 20V, Positive-QTOF	splash10-002r-0000095000-a7901bdbe73ff9fe0817	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metrizoic acid 40V, Positive-QTOF	splash10-014l-1000090000-a04210216d71581c345a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metrizoic acid 10V, Negative-QTOF	splash10-003r-0000095000-d9996e619e95344f4c7e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metrizoic acid 20V, Negative-QTOF	splash10-001i-1000093000-61533ade0cd07f17dbeb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metrizoic acid 40V, Negative-QTOF	splash10-0006-3000090000-d8a3938ce1a40d978375	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metrizoic acid 10V, Negative-QTOF	splash10-0059-0000069000-f53a51dd82fa4ae4645d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metrizoic acid 20V, Negative-QTOF	splash10-0059-0000098000-260af3d8cba3fcdacac0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metrizoic acid 40V, Negative-QTOF	splash10-004l-1200090000-f3345c8587885c718637	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metrizoic acid 10V, Positive-QTOF	splash10-004i-0000009000-e7a3649b0ce867308ff6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metrizoic acid 20V, Positive-QTOF	splash10-00p0-0000089000-6fdb10993f35cd4ce27d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metrizoic acid 40V, Positive-QTOF	splash10-00kf-0000190000-25e4ae23509345dbe296	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09346

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14165

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metrizoic_Acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

34847

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Metrizoic acid (HMDB0254687)

MOL for HMDB0254687 (Metrizoic acid)

3D MOL for HMDB0254687 (Metrizoic acid)

3D SDF for HMDB0254687 (Metrizoic acid)

3D-SDF for HMDB0254687 (Metrizoic acid)

PDB for HMDB0254687 (Metrizoic acid)

3D PDB for HMDB0254687 (Metrizoic acid)

SMILES for HMDB0254687 (Metrizoic acid)

INCHI for HMDB0254687 (Metrizoic acid)

Structure for HMDB0254687 (Metrizoic acid)

3D Structure for HMDB0254687 (Metrizoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra