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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:20:42 UTC

Update Date

2021-09-26 23:07:58 UTC

HMDB ID

HMDB0254158

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lonidamine

Description

Lonidamine, also known as doridamina or DICA, belongs to the class of organic compounds known as indazoles. Indazoles are compounds containing an indazole, which is structurally characterized by a pyrazole fused to a benzene. Based on a literature review a significant number of articles have been published on Lonidamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lonidamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lonidamine 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

HMDB0254158
     RDKit          3D
Lonidamine
 31 33  0  0  0  0  0  0  0  0999 V2000
    4.4750    1.6610   -0.1437 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3636    2.0728   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1885    3.4461   -0.7573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566    1.1495   -0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856    1.4265   -1.0587 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    0.3259   -1.0942 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1022    0.2325   -1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0976    0.3648   -0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249   -0.7776    0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6854   -0.7475    1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0515    0.4269    1.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2783    0.4729    2.8918 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4499    1.5812    1.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4857    1.5463    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    2.9959   -0.4009 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0529   -0.6941   -0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -2.0694   -0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952   -2.9119   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469   -2.4055    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3435   -1.0296   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3218   -0.2011   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    3.9480   -0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -0.7206   -2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3738    1.0210   -2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4889   -1.7600   -0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1507   -1.6823    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7099    2.5407    1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963   -2.5160   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7656   -3.9743   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9338   -3.0540    0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3578   -0.6681    0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  4  1  0
 14  8  1  0
 21 16  1  0
  3 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 13 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END


  Mrv0541 02231218162D          

 21 23  0  0  0  0            999 V2000
    4.6285   -2.5604    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.3450   -1.6726    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    2.0742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649    2.5182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -0.2079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411    0.4560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -1.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596    1.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795   -1.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4742   -0.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159    1.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868   -2.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2814   -0.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5378   -1.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  2 21  1  0  0  0  0
  3 18  1  0  0  0  0
  4 18  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6 11  2  0  0  0  0
  7  9  1  0  0  0  0
  7 12  2  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 13  2  0  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 11 18  1  0  0  0  0
 12 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 17  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254158

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=NN(CC2=C(Cl)C=C(Cl)C=C2)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H10Cl2N2O2/c16-10-6-5-9(12(17)7-10)8-19-13-4-2-1-3-11(13)14(18-19)15(20)21/h1-7H,8H2,(H,20,21)

> <INCHI_KEY>
WDRYRZXSPDWGEB-UHFFFAOYSA-N

> <FORMULA>
C15H10Cl2N2O2

> <MOLECULAR_WEIGHT>
321.158

> <EXACT_MASS>
320.011932988

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.404231112514907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2,4-dichlorophenyl)methyl]-1H-indazole-3-carboxylic acid

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
4.395979457666666

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1167056991265354

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6333908705342477

> <JCHEM_POLAR_SURFACE_AREA>
55.12

> <JCHEM_REFRACTIVITY>
92.39550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DICA

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254158
     RDKit          3D
Lonidamine
 31 33  0  0  0  0  0  0  0  0999 V2000
    4.4750    1.6610   -0.1437 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3636    2.0728   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1885    3.4461   -0.7573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566    1.1495   -0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856    1.4265   -1.0587 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    0.3259   -1.0942 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1022    0.2325   -1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0976    0.3648   -0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249   -0.7776    0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6854   -0.7475    1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0515    0.4269    1.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2783    0.4729    2.8918 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4499    1.5812    1.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4857    1.5463    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    2.9959   -0.4009 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0529   -0.6941   -0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -2.0694   -0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952   -2.9119   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469   -2.4055    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3435   -1.0296   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3218   -0.2011   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    3.9480   -0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -0.7206   -2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3738    1.0210   -2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4889   -1.7600   -0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1507   -1.6823    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7099    2.5407    1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963   -2.5160   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7656   -3.9743   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9338   -3.0540    0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3578   -0.6681    0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  4  1  0
 14  8  1  0
 21 16  1  0
  3 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 13 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       8.640  -4.779   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0      13.711  -3.122   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       9.190   3.872   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.654   4.701   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.205  -0.388   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.103   0.851   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.747   0.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.683  -1.852   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747   1.621   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.190  -2.169   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.205   2.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -0.689   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   2.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   0.081   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.668  -3.633   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.219  -1.023   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080   1.621   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.683   3.554   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.175  -3.951   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.725  -1.341   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.204  -2.805   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   21                                                            
CONECT    3   18                                                            
CONECT    4   18                                                            
CONECT    5    6    7    8                                                  
CONECT    6    5   11                                                       
CONECT    7    5    9   12                                                  
CONECT    8    5   10                                                       
CONECT    9    7   11   13                                                  
CONECT   10    8   15   16                                                  
CONECT   11    6    9   18                                                  
CONECT   12    7   14                                                       
CONECT   13    9   17                                                       
CONECT   14   12   17                                                       
CONECT   15    1   10   19                                                  
CONECT   16   10   20                                                       
CONECT   17   13   14                                                       
CONECT   18    3    4   11                                                  
CONECT   19   15   21                                                       
CONECT   20   16   21                                                       
CONECT   21    2   19   20                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0254158
HETATM    1  O1  UNL     1       4.475   1.661  -0.144  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.364   2.073  -0.507  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.188   3.446  -0.757  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.257   1.150  -0.672  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.986   1.426  -1.059  1.00  0.00           N  
HETATM    6  N2  UNL     1       0.264   0.326  -1.094  1.00  0.00           N  
HETATM    7  C3  UNL     1      -1.102   0.232  -1.460  1.00  0.00           C  
HETATM    8  C4  UNL     1      -2.098   0.365  -0.407  1.00  0.00           C  
HETATM    9  C5  UNL     1      -2.725  -0.778   0.055  1.00  0.00           C  
HETATM   10  C6  UNL     1      -3.685  -0.748   1.052  1.00  0.00           C  
HETATM   11  C7  UNL     1      -4.052   0.427   1.621  1.00  0.00           C  
HETATM   12 CL1  UNL     1      -5.278   0.473   2.892  1.00  0.00          CL  
HETATM   13  C8  UNL     1      -3.450   1.581   1.189  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.486   1.546   0.187  1.00  0.00           C  
HETATM   15 CL2  UNL     1      -1.691   2.996  -0.401  1.00  0.00          CL  
HETATM   16  C10 UNL     1       1.053  -0.694  -0.729  1.00  0.00           C  
HETATM   17  C11 UNL     1       0.868  -2.069  -0.577  1.00  0.00           C  
HETATM   18  C12 UNL     1       1.895  -2.912  -0.174  1.00  0.00           C  
HETATM   19  C13 UNL     1       3.147  -2.405   0.093  1.00  0.00           C  
HETATM   20  C14 UNL     1       3.344  -1.030  -0.055  1.00  0.00           C  
HETATM   21  C15 UNL     1       2.322  -0.201  -0.455  1.00  0.00           C  
HETATM   22  H1  UNL     1       2.504   3.948  -0.219  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.337  -0.721  -2.025  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.374   1.021  -2.236  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.489  -1.760  -0.349  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.151  -1.682   1.381  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.710   2.541   1.613  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.096  -2.516  -0.775  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.766  -3.974  -0.053  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.934  -3.054   0.402  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.358  -0.668   0.168  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   22
CONECT    4    5    5   21
CONECT    5    6
CONECT    6    7   16
CONECT    7    8   23   24
CONECT    8    9    9   14
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12   13
CONECT   13   14   14   27
CONECT   14   15
CONECT   16   17   17   21
CONECT   17   18   28
CONECT   18   19   19   29
CONECT   19   20   30
CONECT   20   21   21   31
END

HMDB0254158
     RDKit          3D
Lonidamine
 31 33  0  0  0  0  0  0  0  0999 V2000
    4.4750    1.6610   -0.1437 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3636    2.0728   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1885    3.4461   -0.7573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566    1.1495   -0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9856    1.4265   -1.0587 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    0.3259   -1.0942 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1022    0.2325   -1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0976    0.3648   -0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249   -0.7776    0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6854   -0.7475    1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0515    0.4269    1.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2783    0.4729    2.8918 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4499    1.5812    1.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4857    1.5463    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    2.9959   -0.4009 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0529   -0.6941   -0.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -2.0694   -0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952   -2.9119   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469   -2.4055    0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3435   -1.0296   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3218   -0.2011   -0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    3.9480   -0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -0.7206   -2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3738    1.0210   -2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4889   -1.7600   -0.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1507   -1.6823    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7099    2.5407    1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963   -2.5160   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7656   -3.9743   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9338   -3.0540    0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3578   -0.6681    0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  4  1  0
 14  8  1  0
 21 16  1  0
  3 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 13 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2,4-Dichlorbenzyl)-indazole-3-carboxylic acid	ChEBI
DICA	ChEBI
Diclondazolic acid	ChEBI
Doridamina	ChEBI
Lonidamin	ChEBI
Lonidamina	ChEBI
Lonidaminum	ChEBI
1-(2,4-Dichlorbenzyl)-indazole-3-carboxylate	Generator
Diclondazolate	Generator
1-(2,4-Dichlorobenzyl)indazole-3-carboxylic acid	MeSH

Chemical Formula

C₁₅H₁₀Cl₂N₂O₂

Average Molecular Weight

321.158

Monoisotopic Molecular Weight

320.011932988

IUPAC Name

1-[(2,4-dichlorophenyl)methyl]-1H-indazole-3-carboxylic acid

Traditional Name

DICA

CAS Registry Number

Not Available

SMILES

OC(=O)C1=NN(CC2=C(Cl)C=C(Cl)C=C2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C15H10Cl2N2O2/c16-10-6-5-9(12(17)7-10)8-19-13-4-2-1-3-11(13)14(18-19)15(20)21/h1-7H,8H2,(H,20,21)

InChI Key

WDRYRZXSPDWGEB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indazoles. Indazoles are compounds containing an indazole, which is structurally characterized by a pyrazole fused to a benzene.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrazoles

Sub Class

Indazoles

Direct Parent

Indazoles

Alternative Parents

Substituents

Benzopyrazole
Indazole
Pyrazole-3-carboxylic acid or derivatives
Pyrazole-5-carboxylic acid or derivatives
1,3-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Azole
Heteroaromatic compound
Pyrazole
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organochloride
Organopnictogen compound
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:50138 )
dichlorobenzene (CHEBI:50138 )
indazoles (CHEBI:50138 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.9	ALOGPS
logP	4.4	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.12	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.4 m³·mol⁻¹	ChemAxon
Polarizability	30.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	197.779	30932474
DeepCCS	[M+Na]+	173.344	30932474
AllCCS	[M+H]+	166.7	32859911
AllCCS	[M+H-H2O]+	163.4	32859911
AllCCS	[M+NH4]+	169.8	32859911
AllCCS	[M+Na]+	170.7	32859911
AllCCS	[M-H]-	162.0	32859911
AllCCS	[M+Na-2H]-	160.9	32859911
AllCCS	[M+HCOO]-	159.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lonidamine	OC(=O)C1=NN(CC2=C(Cl)C=C(Cl)C=C2)C2=CC=CC=C12	3806.4	Standard polar	33892256
Lonidamine	OC(=O)C1=NN(CC2=C(Cl)C=C(Cl)C=C2)C2=CC=CC=C12	2618.3	Standard non polar	33892256
Lonidamine	OC(=O)C1=NN(CC2=C(Cl)C=C(Cl)C=C2)C2=CC=CC=C12	2807.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lonidamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bt9-0950000000-b2196a9235102d3b34cc	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lonidamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lonidamine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lonidamine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lonidamine LC-ESI-qTof , Positive-QTOF	splash10-0pb9-0907000000-8c1504c16c85b7a25213	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lonidamine LC-ESI-qTof , Positive-QTOF	splash10-0udi-3900000000-5f778f763f3c6e93fd1e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lonidamine , positive-QTOF	splash10-0pb9-0907000000-8c1504c16c85b7a25213	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lonidamine , positive-QTOF	splash10-0bt9-2900000000-7658029adb35b1dd05c8	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 10V, Positive-QTOF	splash10-00di-0009000000-4b4d5c1e39496460102d	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 20V, Positive-QTOF	splash10-00di-0029000000-6abac0d87d6e823362f1	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 40V, Positive-QTOF	splash10-0ik9-2962000000-cdf78c210fd94e39ad55	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 10V, Negative-QTOF	splash10-014i-0049000000-ef1c26e4c22b2a6b368b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 20V, Negative-QTOF	splash10-016s-0096000000-b28f1de9a4c61b26219b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 40V, Negative-QTOF	splash10-0002-2690000000-87377fd8e418393bd132	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 10V, Positive-QTOF	splash10-0fk9-0009000000-f9ef8857dfe55a3852ec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 20V, Positive-QTOF	splash10-0fb9-0295000000-4660807fa4afd9793c44	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 40V, Positive-QTOF	splash10-0a4i-1970000000-91c1fb97619cf2096b8e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 10V, Negative-QTOF	splash10-004i-0093000000-7d14e0cb1612dba9209c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 20V, Negative-QTOF	splash10-004i-0092000000-f2c972e33623558b4ed0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonidamine 40V, Negative-QTOF	splash10-00b9-0190000000-53c1d3f1aadb8896b98f	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

DB06266

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

36170

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lonidamine

METLIN ID

Not Available

PubChem Compound

39562

PDB ID

Not Available

ChEBI ID

50138

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 Lonidamine (HMDB0254158)

MOL for HMDB0254158 (Lonidamine)

3D MOL for HMDB0254158 (Lonidamine)

3D SDF for HMDB0254158 (Lonidamine)

3D-SDF for HMDB0254158 (Lonidamine)

PDB for HMDB0254158 (Lonidamine)

3D PDB for HMDB0254158 (Lonidamine)

SMILES for HMDB0254158 (Lonidamine)

INCHI for HMDB0254158 (Lonidamine)

Structure for HMDB0254158 (Lonidamine)

3D Structure for HMDB0254158 (Lonidamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra