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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:27 UTC

Update Date

2022-03-07 02:53:07 UTC

HMDB ID

HMDB0031785

Secondary Accession Numbers

HMDB31785

Metabolite Identification

Common Name

Robenidine

Description

Robenidine, also known as robenz or khimkoktsid, belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. Based on a literature review very few articles have been published on Robenidine.

Structure

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

HMDB0031785
     RDKit          3D
Robenidine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.3315   -2.5068    0.0768 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155   -1.8551    0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7951   -0.6556    1.3733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529   -0.7255    2.3102 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9574   -0.4020    2.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650    0.1274    1.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9406    0.4250    1.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6702    0.9388    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0822    1.1872   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0674    1.8422   -2.3967 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7451    0.9039   -1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0028    0.3808   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9056   -2.3291    0.6725 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0351   -1.5350    0.5210 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3134   -0.8348   -0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5111   -0.0220   -0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7374    0.6992   -1.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8800    1.4929   -1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8108    1.5672   -0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2208    2.5760   -1.0862 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5779    0.8390    0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4502    0.0589    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1688   -3.3891   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443    0.2109    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6150   -0.5363    3.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4586    0.2513    2.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7255    1.1559    0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673    1.0919   -2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9725    0.1857   -0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0839   -3.3686    0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248   -0.8498   -1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097    0.6505   -2.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0649    2.0673   -2.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2828    0.8701    1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2695   -0.5125    1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 12  6  1  0
 22 16  1  0
  1 23  1  0
  3 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
 21 34  1  0
 22 35  1  0
M  END

  Mrv0541 05061306082D          

 22 23  0  0  0  0            999 V2000
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
 11  1  2  0  0  0  0
 11  2  1  0  0  0  0
 11  9  1  0  0  0  0
 12  3  2  0  0  0  0
 12  4  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  2  0  0  0  0
 19  9  2  0  0  0  0
 20 10  2  0  0  0  0
 21 15  1  0  0  0  0
 21 19  1  0  0  0  0
 22 15  1  0  0  0  0
 22 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031785

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=C(\C=N\NC(=N)N\N=C/C2=CC=C(Cl)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H13Cl2N5/c16-13-5-1-11(2-6-13)9-19-21-15(18)22-20-10-12-3-7-14(17)8-4-12/h1-10H,(H3,18,21,22)/b19-9-,20-10+

> <INCHI_KEY>
MOOFYEJFXBSZGE-KFSYKRRRSA-N

> <FORMULA>
C15H13Cl2N5

> <MOLECULAR_WEIGHT>
334.203

> <EXACT_MASS>
333.054800855

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.800869407873982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(E)-[(4-chlorophenyl)methylidene]amino]-3-[(Z)-[(4-chlorophenyl)methylidene]amino]guanidine

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
4.379414271

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.391619565489506

> <JCHEM_PKA_STRONGEST_BASIC>
4.985132028145159

> <JCHEM_POLAR_SURFACE_AREA>
72.63

> <JCHEM_REFRACTIVITY>
122.65220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(E)-[(4-chlorophenyl)methylidene]amino]-3-[(Z)-[(4-chlorophenyl)methylidene]amino]guanidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031785
     RDKit          3D
Robenidine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.3315   -2.5068    0.0768 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155   -1.8551    0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7951   -0.6556    1.3733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529   -0.7255    2.3102 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9574   -0.4020    2.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650    0.1274    1.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9406    0.4250    1.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6702    0.9388    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0822    1.1872   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0674    1.8422   -2.3967 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7451    0.9039   -1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0028    0.3808   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9056   -2.3291    0.6725 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0351   -1.5350    0.5210 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3134   -0.8348   -0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5111   -0.0220   -0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7374    0.6992   -1.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8800    1.4929   -1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8108    1.5672   -0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2208    2.5760   -1.0862 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5779    0.8390    0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4502    0.0589    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1688   -3.3891   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443    0.2109    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6150   -0.5363    3.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4586    0.2513    2.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7255    1.1559    0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673    1.0919   -2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9725    0.1857   -0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0839   -3.3686    0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248   -0.8498   -1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097    0.6505   -2.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0649    2.0673   -2.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2828    0.8701    1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2695   -0.5125    1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 12  6  1  0
 22 16  1  0
  1 23  1  0
  3 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
 21 34  1  0
 22 35  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -18.672   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -17.338   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -20.005   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -18.672   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -16.004   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -17.338   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -20.005   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.003   3.850   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      -8.002  10.780   0.000  0.00  0.00          Cl+0
HETATM   17 Cl   UNK     0     -21.339   1.540   0.000  0.00  0.00          Cl+0
HETATM   18  N   UNK     0     -12.003   2.310   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -9.336   3.850   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0     -14.671   3.850   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0     -10.669   4.620   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0     -13.337   4.620   0.000  0.00  0.00           N+0
CONECT    1    5   11                                                       
CONECT    2    6   11                                                       
CONECT    3    7   12                                                       
CONECT    4    8   12                                                       
CONECT    5    1   13                                                       
CONECT    6    2   13                                                       
CONECT    7    3   14                                                       
CONECT    8    4   14                                                       
CONECT    9   11   19                                                       
CONECT   10   12   20                                                       
CONECT   11    1    2    9                                                  
CONECT   12    3    4   10                                                  
CONECT   13    5    6   16                                                  
CONECT   14    7    8   17                                                  
CONECT   15   18   21   22                                                  
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19    9   21                                                       
CONECT   20   10   22                                                       
CONECT   21   15   19                                                       
CONECT   22   15   20                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0031785
HETATM    1  N1  UNL     1      -1.331  -2.507   0.077  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.416  -1.855   0.690  1.00  0.00           C  
HETATM    3  N2  UNL     1      -0.795  -0.656   1.373  1.00  0.00           N  
HETATM    4  N3  UNL     1      -1.753  -0.725   2.310  1.00  0.00           N  
HETATM    5  C2  UNL     1      -2.957  -0.402   2.214  1.00  0.00           C  
HETATM    6  C3  UNL     1      -3.565   0.127   1.032  1.00  0.00           C  
HETATM    7  C4  UNL     1      -4.941   0.425   1.145  1.00  0.00           C  
HETATM    8  C5  UNL     1      -5.670   0.939   0.103  1.00  0.00           C  
HETATM    9  C6  UNL     1      -5.082   1.187  -1.109  1.00  0.00           C  
HETATM   10 CL1  UNL     1      -6.067   1.842  -2.397  1.00  0.00          CL  
HETATM   11  C7  UNL     1      -3.745   0.904  -1.237  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.003   0.381  -0.176  1.00  0.00           C  
HETATM   13  N4  UNL     1       0.906  -2.329   0.673  1.00  0.00           N  
HETATM   14  N5  UNL     1       2.035  -1.535   0.521  1.00  0.00           N  
HETATM   15  C9  UNL     1       2.313  -0.835  -0.505  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.511  -0.022  -0.608  1.00  0.00           C  
HETATM   17  C11 UNL     1       3.737   0.699  -1.740  1.00  0.00           C  
HETATM   18  C12 UNL     1       4.880   1.493  -1.875  1.00  0.00           C  
HETATM   19  C13 UNL     1       5.811   1.567  -0.863  1.00  0.00           C  
HETATM   20 CL2  UNL     1       7.221   2.576  -1.086  1.00  0.00          CL  
HETATM   21  C14 UNL     1       5.578   0.839   0.275  1.00  0.00           C  
HETATM   22  C15 UNL     1       4.450   0.059   0.401  1.00  0.00           C  
HETATM   23  H1  UNL     1      -1.169  -3.389  -0.451  1.00  0.00           H  
HETATM   24  H2  UNL     1      -0.244   0.211   1.084  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.615  -0.536   3.125  1.00  0.00           H  
HETATM   26  H4  UNL     1      -5.459   0.251   2.073  1.00  0.00           H  
HETATM   27  H5  UNL     1      -6.726   1.156   0.224  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.267   1.092  -2.179  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.973   0.186  -0.347  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.084  -3.369   0.781  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.625  -0.850  -1.332  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.010   0.651  -2.550  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.065   2.067  -2.770  1.00  0.00           H  
HETATM   34  H12 UNL     1       6.283   0.870   1.091  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.270  -0.512   1.296  1.00  0.00           H  
CONECT    1    2    2   23
CONECT    2    3   13
CONECT    3    4   24
CONECT    4    5    5
CONECT    5    6   25
CONECT    6    7    7   12
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10   11
CONECT   11   12   12   28
CONECT   12   29
CONECT   13   14   30
CONECT   14   15   15
CONECT   15   16   31
CONECT   16   17   17   22
CONECT   17   18   32
CONECT   18   19   19   33
CONECT   19   20   21
CONECT   21   22   22   34
CONECT   22   35
END

HMDB0031785
     RDKit          3D
Robenidine
 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.3315   -2.5068    0.0768 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155   -1.8551    0.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7951   -0.6556    1.3733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529   -0.7255    2.3102 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9574   -0.4020    2.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650    0.1274    1.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9406    0.4250    1.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6702    0.9388    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0822    1.1872   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0674    1.8422   -2.3967 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7451    0.9039   -1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0028    0.3808   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9056   -2.3291    0.6725 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0351   -1.5350    0.5210 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3134   -0.8348   -0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5111   -0.0220   -0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7374    0.6992   -1.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8800    1.4929   -1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8108    1.5672   -0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2208    2.5760   -1.0862 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5779    0.8390    0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4502    0.0589    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1688   -3.3891   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443    0.2109    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6150   -0.5363    3.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4586    0.2513    2.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7255    1.1559    0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673    1.0919   -2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9725    0.1857   -0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0839   -3.3686    0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248   -0.8498   -1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097    0.6505   -2.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0649    2.0673   -2.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2828    0.8701    1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2695   -0.5125    1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 12  6  1  0
 22 16  1  0
  1 23  1  0
  3 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
 21 34  1  0
 22 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3-Bis((p-chlorobenzylidene)amino)-guanidine	HMDB
1,3-Bis((p-chlorobenzylidene)amino)guanidine	HMDB
1,3-Bis[(p-chlorobenzylidene)amino]guanidine, 8ci	HMDB
Bis((4-chlorophenyl)methylene)-carbonimidic dihydrazide	HMDB
Bis[(4-chlorophenyl)methylene]-carbonimidic dihydrazide	HMDB
Bis[(4-chlorophenyl)methylene]carbonimidic dihydrazide, 9ci	HMDB
Chimcoccide	HMDB
Khimcoccid	HMDB
Khimkoktsid	HMDB
Khimkoktside	HMDB
Robenidina	HMDB
Robenidine hydrochloride	HMDB
Robenidinum	HMDB
Robenz	HMDB
Robenzidene	HMDB
Robenzidine	HMDB
Alpharma brand OF robenidine hydrochloride	HMDB
Cytostat	HMDB
Hydrochloride, robenidine	HMDB
Robenidine	MeSH

Chemical Formula

C₁₅H₁₃Cl₂N₅

Average Molecular Weight

334.203

Monoisotopic Molecular Weight

333.054800855

IUPAC Name

1-[(E)-[(4-chlorophenyl)methylidene]amino]-3-[(Z)-[(4-chlorophenyl)methylidene]amino]guanidine

Traditional Name

1-[(E)-[(4-chlorophenyl)methylidene]amino]-3-[(Z)-[(4-chlorophenyl)methylidene]amino]guanidine

CAS Registry Number

25875-51-8

SMILES

ClC1=CC=C(\C=N\NC(=N)N\N=C/C2=CC=C(Cl)C=C2)C=C1

InChI Identifier

InChI=1S/C15H13Cl2N5/c16-13-5-1-11(2-6-13)9-19-21-15(18)22-20-10-12-3-7-14(17)8-4-12/h1-10H,(H3,18,21,22)/b19-9-,20-10+

InChI Key

MOOFYEJFXBSZGE-KFSYKRRRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Chlorobenzenes

Alternative Parents

Substituents

Chlorobenzene
Aryl halide
Aryl chloride
Hydrazidine
Guanidine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031785)
Cytoplasm (HMDB: HMDB0031785)

Source

Exogenous

Exogenous (HMDB: HMDB0031785)

Food

Food (HMDB: HMDB0031785)

Endogenous

Endogenous (HMDB: HMDB0031785)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0086 g/L	ALOGPS
logP	1.98	ALOGPS
logP	4.38	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	19.39	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	72.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.65 m³·mol⁻¹	ChemAxon
Polarizability	31.8 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	178.28	30932474
DeepCCS	[M-H]-	175.922	30932474
DeepCCS	[M-2H]-	209.656	30932474
DeepCCS	[M+Na]+	184.883	30932474
AllCCS	[M+H]+	173.8	32859911
AllCCS	[M+H-H2O]+	170.6	32859911
AllCCS	[M+NH4]+	176.7	32859911
AllCCS	[M+Na]+	177.6	32859911
AllCCS	[M-H]-	171.6	32859911
AllCCS	[M+Na-2H]-	171.0	32859911
AllCCS	[M+HCOO]-	170.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Robenidine	ClC1=CC=C(\C=N\NC(=N)N\N=C/C2=CC=C(Cl)C=C2)C=C1	3725.2	Standard polar	33892256
Robenidine	ClC1=CC=C(\C=N\NC(=N)N\N=C/C2=CC=C(Cl)C=C2)C=C1	2061.3	Standard non polar	33892256
Robenidine	ClC1=CC=C(\C=N\NC(=N)N\N=C/C2=CC=C(Cl)C=C2)C=C1	3426.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Robenidine,1TMS,isomer #1	C[Si](C)(C)N(/N=C/C1=CC=C(Cl)C=C1)C(=N)N/N=C\C1=CC=C(Cl)C=C1	3205.5	Semi standard non polar	33892256
Robenidine,1TMS,isomer #1	C[Si](C)(C)N(/N=C/C1=CC=C(Cl)C=C1)C(=N)N/N=C\C1=CC=C(Cl)C=C1	3296.8	Standard non polar	33892256
Robenidine,1TMS,isomer #2	C[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N/N=C/C1=CC=C(Cl)C=C1	3213.2	Semi standard non polar	33892256
Robenidine,1TMS,isomer #2	C[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N/N=C/C1=CC=C(Cl)C=C1	3108.9	Standard non polar	33892256
Robenidine,1TMS,isomer #3	C[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N/N=C/C1=CC=C(Cl)C=C1	3205.5	Semi standard non polar	33892256
Robenidine,1TMS,isomer #3	C[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N/N=C/C1=CC=C(Cl)C=C1	3296.8	Standard non polar	33892256
Robenidine,2TMS,isomer #1	C[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C	3113.1	Semi standard non polar	33892256
Robenidine,2TMS,isomer #1	C[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C	3178.9	Standard non polar	33892256
Robenidine,2TMS,isomer #2	C[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C	3085.1	Semi standard non polar	33892256
Robenidine,2TMS,isomer #2	C[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C	3286.9	Standard non polar	33892256
Robenidine,2TMS,isomer #3	C[Si](C)(C)N=C(N/N=C/C1=CC=C(Cl)C=C1)N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C	3113.1	Semi standard non polar	33892256
Robenidine,2TMS,isomer #3	C[Si](C)(C)N=C(N/N=C/C1=CC=C(Cl)C=C1)N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C	3178.9	Standard non polar	33892256
Robenidine,3TMS,isomer #1	C[Si](C)(C)N=C(N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C	3158.4	Semi standard non polar	33892256
Robenidine,3TMS,isomer #1	C[Si](C)(C)N=C(N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C	3054.1	Standard non polar	33892256
Robenidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(/N=C/C1=CC=C(Cl)C=C1)C(=N)N/N=C\C1=CC=C(Cl)C=C1	3386.9	Semi standard non polar	33892256
Robenidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(/N=C/C1=CC=C(Cl)C=C1)C(=N)N/N=C\C1=CC=C(Cl)C=C1	3419.6	Standard non polar	33892256
Robenidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N/N=C/C1=CC=C(Cl)C=C1	3412.8	Semi standard non polar	33892256
Robenidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N/N=C/C1=CC=C(Cl)C=C1	3286.6	Standard non polar	33892256
Robenidine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N/N=C/C1=CC=C(Cl)C=C1	3386.9	Semi standard non polar	33892256
Robenidine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N/N=C/C1=CC=C(Cl)C=C1	3419.6	Standard non polar	33892256
Robenidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3491.5	Semi standard non polar	33892256
Robenidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3481.6	Standard non polar	33892256
Robenidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3511.0	Semi standard non polar	33892256
Robenidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3569.7	Standard non polar	33892256
Robenidine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(N/N=C/C1=CC=C(Cl)C=C1)N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3491.5	Semi standard non polar	33892256
Robenidine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(N/N=C/C1=CC=C(Cl)C=C1)N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3481.6	Standard non polar	33892256
Robenidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3754.4	Semi standard non polar	33892256
Robenidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3566.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Robenidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-0901000000-bd3c64c75f0b6bd6835f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Robenidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Robenidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 10V, Positive-QTOF	splash10-001i-0509000000-1340b46a98b339692f08	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 20V, Positive-QTOF	splash10-0040-0902000000-b8ecacc20a50391b5c94	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 40V, Positive-QTOF	splash10-000i-1900000000-ab4e9201f85a37fc505b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 10V, Negative-QTOF	splash10-001i-0609000000-36085c7522e6c99f1457	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 20V, Negative-QTOF	splash10-0udi-0901000000-600675618f3b0670cb14	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 40V, Negative-QTOF	splash10-0ikl-2900000000-48681aecdbfff61982f0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 10V, Negative-QTOF	splash10-001i-0209000000-c91fff2e7cc4e42fe9e9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 20V, Negative-QTOF	splash10-0f89-9803000000-c66e0d086dd888852953	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 40V, Negative-QTOF	splash10-001i-9000000000-0c585b3615c9542786b2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 10V, Positive-QTOF	splash10-001i-0309000000-c043134b850721f887e1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 20V, Positive-QTOF	splash10-003r-0900000000-b6505f3eb5f43ed1fac1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Robenidine 40V, Positive-QTOF	splash10-002r-0900000000-fcc19c5c36922ed2bd4f	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008458

KNApSAcK ID

Not Available

Chemspider ID

17946882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Robenidine

METLIN ID

Not Available

PubChem Compound

18527351

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Robenidine (HMDB0031785)

MOL for HMDB0031785 (Robenidine)

3D MOL for HMDB0031785 (Robenidine)

3D SDF for HMDB0031785 (Robenidine)

3D-SDF for HMDB0031785 (Robenidine)

PDB for HMDB0031785 (Robenidine)

3D PDB for HMDB0031785 (Robenidine)

SMILES for HMDB0031785 (Robenidine)

INCHI for HMDB0031785 (Robenidine)

Structure for HMDB0031785 (Robenidine)

3D Structure for HMDB0031785 (Robenidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra