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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:20:04 UTC

Update Date

2021-09-26 23:01:44 UTC

HMDB ID

HMDB0250329

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Clobenpropit

Description

clobenpropit belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. clobenpropit is a very strong basic compound (based on its pKa). Also displays partial agonist activity at H4 receptors; induces eosinophil shape change with an EC50 of 3 nM. An extremely potent histamine H3 antagonist/inverse agonist (pA2 = 9.93). An imidothiocarbamic ester that consists of isothiourea bearing S-3-(imidazol-4-yl)propyl and N-4-chlorobenzyl substituents. This compound has been identified in human blood as reported by (PMID: 31557052 ). Clobenpropit is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Clobenpropit 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

HMDB0250329
     RDKit          3D
Clobenpropit
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.2205    0.7200    1.5858 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -0.0054    0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7218    0.3989    0.2752 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4675   -0.3563   -0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9037   -0.1630   -0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5815   -1.0079    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9177   -0.8185    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6228    0.2118    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3421    0.4451    0.5047 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9634    1.0731   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6101    0.8676   -0.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0910   -1.4870   -0.1329 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7485   -1.7921    0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6454   -0.6935    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0643   -0.8337    0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8339    0.3167    0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1744    0.5385    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5293    1.6650   -0.3892 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4361    2.1397   -1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4194    1.3195   -0.7608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4759    1.7136    1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5436    0.2089    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827   -1.4245   -0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614    0.0404   -1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0093   -1.8309    0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4147   -1.4916    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5221    1.8830   -1.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1330    1.5577   -1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0668   -2.7875    0.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204   -1.8832    1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643    0.2635    0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5927   -0.6684   -1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5349   -1.7884    0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0941   -0.7432    1.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8360   -0.0764    0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    3.0458   -1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496    1.4427   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 20 16  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
M  END

  Mrv1533004261514382D          

 20 21  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2309    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0379    0.9920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4504    0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8984   -0.3356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250329

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(SCCCC1=CN=CN1)=NCC1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H17ClN4S/c15-12-5-3-11(4-6-12)8-18-14(16)20-7-1-2-13-9-17-10-19-13/h3-6,9-10H,1-2,7-8H2,(H2,16,18)(H,17,19)

> <INCHI_KEY>
UCAIEVHKDLMIFL-UHFFFAOYSA-N

> <FORMULA>
C14H17ClN4S

> <MOLECULAR_WEIGHT>
308.83

> <EXACT_MASS>
308.0862454

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
33.10309128325491

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N'-[(4-chlorophenyl)methyl]{[3-(1H-imidazol-5-yl)propyl]sulfanyl}methanimidamide

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
2.9652030179999995

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.61421865373633

> <JCHEM_PKA_STRONGEST_BASIC>
8.89651949630503

> <JCHEM_POLAR_SURFACE_AREA>
67.06

> <JCHEM_REFRACTIVITY>
85.8826

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clobenpropit

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250329
     RDKit          3D
Clobenpropit
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.2205    0.7200    1.5858 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -0.0054    0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7218    0.3989    0.2752 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4675   -0.3563   -0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9037   -0.1630   -0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5815   -1.0079    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9177   -0.8185    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6228    0.2118    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3421    0.4451    0.5047 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9634    1.0731   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6101    0.8676   -0.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0910   -1.4870   -0.1329 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7485   -1.7921    0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6454   -0.6935    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0643   -0.8337    0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8339    0.3167    0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1744    0.5385    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5293    1.6650   -0.3892 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4361    2.1397   -1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4194    1.3195   -0.7608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4759    1.7136    1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5436    0.2089    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827   -1.4245   -0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614    0.0404   -1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0093   -1.8309    0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4147   -1.4916    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5221    1.8830   -1.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1330    1.5577   -1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0668   -2.7875    0.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204   -1.8832    1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643    0.2635    0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5927   -0.6684   -1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5349   -1.7884    0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0941   -0.7432    1.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8360   -0.0764    0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    3.0458   -1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496    1.4427   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 20 16  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   11  S   UNK     0       8.002   0.000   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.498   1.532   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      15.004   1.852   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      15.774   0.518   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      14.744  -0.626   0.000  0.00  0.00           N+0
HETATM   20 Cl   UNK     0      -1.334   2.310   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20    3                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0250329
HETATM    1  N1  UNL     1      -0.220   0.720   1.586  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.551  -0.005   0.619  1.00  0.00           C  
HETATM    3  N2  UNL     1       1.722   0.399   0.275  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.468  -0.356  -0.700  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.904  -0.163  -0.404  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.582  -1.008   0.450  1.00  0.00           C  
HETATM    7  C5  UNL     1       5.918  -0.819   0.718  1.00  0.00           C  
HETATM    8  C6  UNL     1       6.623   0.212   0.150  1.00  0.00           C  
HETATM    9 CL1  UNL     1       8.342   0.445   0.505  1.00  0.00          CL  
HETATM   10  C7  UNL     1       5.963   1.073  -0.710  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.610   0.868  -0.972  1.00  0.00           C  
HETATM   12  S1  UNL     1      -0.091  -1.487  -0.133  1.00  0.00           S  
HETATM   13  C9  UNL     1      -1.748  -1.792   0.537  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.645  -0.694   0.066  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.064  -0.834   0.560  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.834   0.317   0.019  1.00  0.00           C  
HETATM   17  C13 UNL     1      -6.174   0.539   0.254  1.00  0.00           C  
HETATM   18  N3  UNL     1      -6.529   1.665  -0.389  1.00  0.00           N  
HETATM   19  C14 UNL     1      -5.436   2.140  -1.013  1.00  0.00           C  
HETATM   20  N4  UNL     1      -4.419   1.319  -0.761  1.00  0.00           N  
HETATM   21  H1  UNL     1      -0.476   1.714   1.495  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.544   0.209   2.435  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.183  -1.425  -0.740  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.261   0.040  -1.734  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.009  -1.831   0.900  1.00  0.00           H  
HETATM   26  H6  UNL     1       6.415  -1.492   1.385  1.00  0.00           H  
HETATM   27  H7  UNL     1       6.522   1.883  -1.155  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.133   1.558  -1.646  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.067  -2.787   0.142  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.720  -1.883   1.648  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.264   0.264   0.477  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.593  -0.668  -1.039  1.00  0.00           H  
HETATM   33  H13 UNL     1      -4.535  -1.788   0.297  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.094  -0.743   1.665  1.00  0.00           H  
HETATM   35  H15 UNL     1      -6.836  -0.076   0.848  1.00  0.00           H  
HETATM   36  H16 UNL     1      -5.464   3.046  -1.604  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.450   1.443  -1.118  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3    3   12
CONECT    3    4
CONECT    4    5   23   24
CONECT    5    6    6   11
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   10
CONECT   10   11   11   27
CONECT   11   28
CONECT   12   13
CONECT   13   14   29   30
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   17   20
CONECT   17   18   35
CONECT   18   19   19
CONECT   19   20   36
CONECT   20   37
END

HMDB0250329
     RDKit          3D
Clobenpropit
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.2205    0.7200    1.5858 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -0.0054    0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7218    0.3989    0.2752 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4675   -0.3563   -0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9037   -0.1630   -0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5815   -1.0079    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9177   -0.8185    0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6228    0.2118    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3421    0.4451    0.5047 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9634    1.0731   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6101    0.8676   -0.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0910   -1.4870   -0.1329 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7485   -1.7921    0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6454   -0.6935    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0643   -0.8337    0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8339    0.3167    0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1744    0.5385    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5293    1.6650   -0.3892 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4361    2.1397   -1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4194    1.3195   -0.7608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4759    1.7136    1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5436    0.2089    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827   -1.4245   -0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614    0.0404   -1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0093   -1.8309    0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4147   -1.4916    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5221    1.8830   -1.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1330    1.5577   -1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0668   -2.7875    0.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204   -1.8832    1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643    0.2635    0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5927   -0.6684   -1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5349   -1.7884    0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0941   -0.7432    1.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8360   -0.0764    0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    3.0458   -1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496    1.4427   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 20 16  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 19 36  1  0
 20 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
S-(3-(4(5)-Imidazolyl))propyl-N-(4-chlorobenzyl)isothiourea	ChEBI

Chemical Formula

C₁₄H₁₇ClN₄S

Average Molecular Weight

308.83

Monoisotopic Molecular Weight

308.0862454

IUPAC Name

N'-[(4-chlorophenyl)methyl]{[3-(1H-imidazol-5-yl)propyl]sulfanyl}methanimidamide

Traditional Name

clobenpropit

CAS Registry Number

Not Available

SMILES

NC(SCCCC1=CN=CN1)=NCC1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C14H17ClN4S/c15-12-5-3-11(4-6-12)8-18-14(16)20-7-1-2-13-9-17-10-19-13/h3-6,9-10H,1-2,7-8H2,(H2,16,18)(H,17,19)

InChI Key

UCAIEVHKDLMIFL-UHFFFAOYSA-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 chloride
Aryl halide
Azole
Heteroaromatic compound
Imidazole
Isothiourea
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Carboximidamide
Organohalogen compound
Organopnictogen compound
Imine
Organic nitrogen compound
Organochloride
Organonitrogen compound
Organosulfur compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:64177 )
organochlorine compound (CHEBI:64177 )
imidothiocarbamic ester (CHEBI:64177 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	3.19	ALOGPS
logP	2.97	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	8.9	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	85.88 m³·mol⁻¹	ChemAxon
Polarizability	33.1 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]+	168.875	30932474
DeepCCS	[M-H]-	166.517	30932474
DeepCCS	[M-2H]-	199.403	30932474
DeepCCS	[M+Na]+	174.969	30932474
AllCCS	[M+H]+	169.5	32859911
AllCCS	[M+H-H2O]+	166.3	32859911
AllCCS	[M+NH4]+	172.5	32859911
AllCCS	[M+Na]+	173.4	32859911
AllCCS	[M-H]-	170.1	32859911
AllCCS	[M+Na-2H]-	170.2	32859911
AllCCS	[M+HCOO]-	170.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clobenpropit	NC(SCCCC1=CN=CN1)=NCC1=CC=C(Cl)C=C1	3732.1	Standard polar	33892256
Clobenpropit	NC(SCCCC1=CN=CN1)=NCC1=CC=C(Cl)C=C1	2800.3	Standard non polar	33892256
Clobenpropit	NC(SCCCC1=CN=CN1)=NCC1=CC=C(Cl)C=C1	3203.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Clobenpropit,1TMS,isomer #1	C[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1	2939.8	Semi standard non polar	33892256
Clobenpropit,1TMS,isomer #1	C[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1	2580.1	Standard non polar	33892256
Clobenpropit,1TMS,isomer #1	C[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1	4085.8	Standard polar	33892256
Clobenpropit,1TMS,isomer #2	C[Si](C)(C)N1C=NC=C1CCCSC(N)=NCC1=CC=C(Cl)C=C1	2950.8	Semi standard non polar	33892256
Clobenpropit,1TMS,isomer #2	C[Si](C)(C)N1C=NC=C1CCCSC(N)=NCC1=CC=C(Cl)C=C1	2638.5	Standard non polar	33892256
Clobenpropit,1TMS,isomer #2	C[Si](C)(C)N1C=NC=C1CCCSC(N)=NCC1=CC=C(Cl)C=C1	4548.5	Standard polar	33892256
Clobenpropit,2TMS,isomer #1	C[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1)[Si](C)(C)C	2991.7	Semi standard non polar	33892256
Clobenpropit,2TMS,isomer #1	C[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1)[Si](C)(C)C	2726.9	Standard non polar	33892256
Clobenpropit,2TMS,isomer #1	C[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1)[Si](C)(C)C	3792.5	Standard polar	33892256
Clobenpropit,2TMS,isomer #2	C[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C	3055.8	Semi standard non polar	33892256
Clobenpropit,2TMS,isomer #2	C[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C	2631.9	Standard non polar	33892256
Clobenpropit,2TMS,isomer #2	C[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C	3870.2	Standard polar	33892256
Clobenpropit,3TMS,isomer #1	C[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C	3082.9	Semi standard non polar	33892256
Clobenpropit,3TMS,isomer #1	C[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C	2754.2	Standard non polar	33892256
Clobenpropit,3TMS,isomer #1	C[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C)[Si](C)(C)C	3541.8	Standard polar	33892256
Clobenpropit,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1	3135.3	Semi standard non polar	33892256
Clobenpropit,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1	2817.2	Standard non polar	33892256
Clobenpropit,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1	4055.9	Standard polar	33892256
Clobenpropit,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC=C1CCCSC(N)=NCC1=CC=C(Cl)C=C1	3150.2	Semi standard non polar	33892256
Clobenpropit,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC=C1CCCSC(N)=NCC1=CC=C(Cl)C=C1	2849.3	Standard non polar	33892256
Clobenpropit,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC=C1CCCSC(N)=NCC1=CC=C(Cl)C=C1	4586.3	Standard polar	33892256
Clobenpropit,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C	3340.6	Semi standard non polar	33892256
Clobenpropit,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C	3090.7	Standard non polar	33892256
Clobenpropit,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=C[NH]1)[Si](C)(C)C(C)(C)C	3738.8	Standard polar	33892256
Clobenpropit,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C(C)(C)C	3439.8	Semi standard non polar	33892256
Clobenpropit,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C(C)(C)C	3041.1	Standard non polar	33892256
Clobenpropit,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C(C)(C)C	3831.0	Standard polar	33892256
Clobenpropit,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3673.0	Semi standard non polar	33892256
Clobenpropit,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3267.3	Standard non polar	33892256
Clobenpropit,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NCC1=CC=C(Cl)C=C1)SCCCC1=CN=CN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3607.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Clobenpropit GC-MS (Non-derivatized) - 70eV, Positive	splash10-0059-6900000000-1df6ca840aa08c44504e	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clobenpropit 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobenpropit 35V, Negative-QTOF	splash10-014i-0900000000-2dd5c1dfca5021d8e32b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobenpropit 35V, Positive-QTOF	splash10-0a4i-0900000000-67cde69dea0a1bd21043	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenpropit 10V, Positive-QTOF	splash10-0a4i-0309000000-7e93f3bfe07767956691	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenpropit 20V, Positive-QTOF	splash10-0a4i-0915000000-7f6251d5e8211057f86b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenpropit 40V, Positive-QTOF	splash10-0a6r-2900000000-9888628351ba22284b5c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenpropit 10V, Negative-QTOF	splash10-0a4i-0019000000-57c7f879cc9239b427bd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenpropit 20V, Negative-QTOF	splash10-0avl-2901000000-d529044fdd21c91cf27b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobenpropit 40V, Negative-QTOF	splash10-053u-9300000000-e13a567eb78a798e090c	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C17934

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clobenpropit

METLIN ID

Not Available

PubChem Compound

2790

PDB ID

Not Available

ChEBI ID

64177

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 Clobenpropit (HMDB0250329)

MOL for HMDB0250329 (Clobenpropit)

3D MOL for HMDB0250329 (Clobenpropit)

3D SDF for HMDB0250329 (Clobenpropit)

3D-SDF for HMDB0250329 (Clobenpropit)

PDB for HMDB0250329 (Clobenpropit)

3D PDB for HMDB0250329 (Clobenpropit)

SMILES for HMDB0250329 (Clobenpropit)

INCHI for HMDB0250329 (Clobenpropit)

Structure for HMDB0250329 (Clobenpropit)

3D Structure for HMDB0250329 (Clobenpropit)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra