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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:39:38 UTC

Update Date

2021-09-26 23:16:34 UTC

HMDB ID

HMDB0259181

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Triclabendazole

Description

Triclabendazole, also known as egaten or fasinex, belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. Based on a literature review a significant number of articles have been published on Triclabendazole. This compound has been identified in human blood as reported by (PMID: 31557052 ). Triclabendazole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Triclabendazole 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

HMDB0259181
     RDKit          3D
Triclabendazole
 30 32  0  0  0  0  0  0  0  0999 V2000
    6.4441   -0.2706   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4492    1.2172   -1.1752 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7774    0.9100   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7416    1.7687   -0.6047 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515    1.1986   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    1.5915    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5829    0.7653    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717    1.1906    0.9694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993    0.6095    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9505    0.1326    1.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1241   -0.4712    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3682   -0.6097   -0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234   -0.1362   -1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7241   -0.3072   -3.0496 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2542    0.4655   -0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0574    1.0655   -2.0042 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2289   -0.5022    1.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3957   -1.5835    1.9308 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0707   -0.8956    0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -0.0713    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3088   -0.2025    0.0117 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3190   -0.9348   -1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9857   -0.8169   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5102   -0.0224   -0.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0789    2.5939   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7851    0.2280    2.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8682   -0.8443    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2913   -1.0843   -0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787   -1.8890    1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -1.0707    0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
  7 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21  3  1  0
 20  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 19 29  1  0
 21 30  1  0
M  END


  Mrv1572004221604192D          

 21 23  0  0  0  0            999 V2000
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    4.8229    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  2  0  0  0  0
 12  6  2  0  0  0  0
 12  8  1  0  0  0  0
 13  7  2  0  0  0  0
 13 11  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17 13  1  0  0  0  0
 18  9  1  0  0  0  0
 18 14  1  0  0  0  0
 19 10  1  0  0  0  0
 19 14  2  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21  1  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259181

> <DATABASE_NAME>
hmdb

> <SMILES>
CSC1=NC2=C(N1)C=C(Cl)C(OC1=CC=CC(Cl)=C1Cl)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H9Cl3N2OS/c1-21-14-18-9-5-8(16)12(6-10(9)19-14)20-11-4-2-3-7(15)13(11)17/h2-6H,1H3,(H,18,19)

> <INCHI_KEY>
NQPDXQQQCQDHHW-UHFFFAOYSA-N

> <FORMULA>
C14H9Cl3N2OS

> <MOLECULAR_WEIGHT>
359.65

> <EXACT_MASS>
357.9501172

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
34.01811180668874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-chloro-5-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1H-1,3-benzodiazole

> <ALOGPS_LOGP>
5.50

> <JCHEM_LOGP>
5.8843923543333325

> <ALOGPS_LOGS>
-5.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.456478383138528

> <JCHEM_PKA_STRONGEST_BASIC>
4.54357029345663

> <JCHEM_POLAR_SURFACE_AREA>
37.91

> <JCHEM_REFRACTIVITY>
87.85589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
triclabendazole

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0259181
     RDKit          3D
Triclabendazole
 30 32  0  0  0  0  0  0  0  0999 V2000
    6.4441   -0.2706   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4492    1.2172   -1.1752 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7774    0.9100   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7416    1.7687   -0.6047 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515    1.1986   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    1.5915    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5829    0.7653    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717    1.1906    0.9694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993    0.6095    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9505    0.1326    1.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1241   -0.4712    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3682   -0.6097   -0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234   -0.1362   -1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7241   -0.3072   -3.0496 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2542    0.4655   -0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0574    1.0655   -2.0042 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2289   -0.5022    1.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3957   -1.5835    1.9308 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0707   -0.8956    0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -0.0713    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3088   -0.2025    0.0117 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3190   -0.9348   -1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9857   -0.8169   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5102   -0.0224   -0.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0789    2.5939   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7851    0.2280    2.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8682   -0.8443    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2913   -1.0843   -0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787   -1.8890    1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -1.0707    0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
  7 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21  3  1  0
 20  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 19 29  1  0
 21 30  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.531   8.233   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.198   9.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.531   6.693   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.864   8.233   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       2.530   9.003   0.000  0.00  0.00          Cl+0
HETATM   16 Cl   UNK     0       5.198   1.303   0.000  0.00  0.00          Cl+0
HETATM   17 Cl   UNK     0       2.530   5.923   0.000  0.00  0.00          Cl+0
HETATM   18  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   21  S   UNK     0      -2.713   2.843   0.000  0.00  0.00           S+0
CONECT    1   21                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2   11                                                       
CONECT    5    8    9                                                       
CONECT    6   10   12                                                       
CONECT    7    3   13   15                                                  
CONECT    8    5   12   16                                                  
CONECT    9    5   10   18                                                  
CONECT   10    6    9   19                                                  
CONECT   11    4   13   20                                                  
CONECT   12    6    8   20                                                  
CONECT   13    7   11   17                                                  
CONECT   14   18   19   21                                                  
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17   13                                                            
CONECT   18    9   14                                                       
CONECT   19   10   14                                                       
CONECT   20   11   12                                                       
CONECT   21    1   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0259181
HETATM    1  C1  UNL     1       6.444  -0.271  -0.875  1.00  0.00           C  
HETATM    2  S1  UNL     1       5.449   1.217  -1.175  1.00  0.00           S  
HETATM    3  C2  UNL     1       3.777   0.910  -0.566  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.742   1.769  -0.605  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.651   1.199  -0.061  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.340   1.592   0.166  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.583   0.765   0.762  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.872   1.191   0.969  1.00  0.00           O  
HETATM    9  C6  UNL     1      -2.999   0.610   0.460  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.950   0.133   1.337  1.00  0.00           C  
HETATM   11  C8  UNL     1      -5.124  -0.471   0.917  1.00  0.00           C  
HETATM   12  C9  UNL     1      -5.368  -0.610  -0.443  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.423  -0.136  -1.335  1.00  0.00           C  
HETATM   14 CL1  UNL     1      -4.724  -0.307  -3.050  1.00  0.00          CL  
HETATM   15  C11 UNL     1      -3.254   0.465  -0.899  1.00  0.00           C  
HETATM   16 CL2  UNL     1      -2.057   1.066  -2.004  1.00  0.00          CL  
HETATM   17  C12 UNL     1      -0.229  -0.502   1.162  1.00  0.00           C  
HETATM   18 CL3  UNL     1      -1.396  -1.583   1.931  1.00  0.00          CL  
HETATM   19  C13 UNL     1       1.071  -0.896   0.939  1.00  0.00           C  
HETATM   20  C14 UNL     1       2.004  -0.071   0.340  1.00  0.00           C  
HETATM   21  N2  UNL     1       3.309  -0.202   0.012  1.00  0.00           N  
HETATM   22  H1  UNL     1       6.319  -0.935  -1.775  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.986  -0.817  -0.039  1.00  0.00           H  
HETATM   24  H3  UNL     1       7.510  -0.022  -0.717  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.079   2.594  -0.156  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.785   0.228   2.413  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.868  -0.844   1.603  1.00  0.00           H  
HETATM   28  H7  UNL     1      -6.291  -1.084  -0.748  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.379  -1.889   1.243  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.866  -1.071   0.194  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5
CONECT    5    6    6   20
CONECT    6    7   25
CONECT    7    8   17   17
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   28
CONECT   13   14   15   15
CONECT   15   16
CONECT   17   18   19
CONECT   19   20   20   29
CONECT   20   21
CONECT   21   30
END

HMDB0259181
     RDKit          3D
Triclabendazole
 30 32  0  0  0  0  0  0  0  0999 V2000
    6.4441   -0.2706   -0.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4492    1.2172   -1.1752 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7774    0.9100   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7416    1.7687   -0.6047 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515    1.1986   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    1.5915    0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5829    0.7653    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8717    1.1906    0.9694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993    0.6095    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9505    0.1326    1.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1241   -0.4712    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3682   -0.6097   -0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234   -0.1362   -1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7241   -0.3072   -3.0496 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2542    0.4655   -0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0574    1.0655   -2.0042 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2289   -0.5022    1.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3957   -1.5835    1.9308 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0707   -0.8956    0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -0.0713    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3088   -0.2025    0.0117 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3190   -0.9348   -1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9857   -0.8169   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5102   -0.0224   -0.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0789    2.5939   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7851    0.2280    2.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8682   -0.8443    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2913   -1.0843   -0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787   -1.8890    1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -1.0707    0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
  7 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21  3  1  0
 20  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 19 29  1  0
 21 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Egaten	Kegg
Fasinex	Kegg
6-Chloro-5-(2,3-dichlorophenoxy)-2-methylthiobenzimidazole	MeSH
Fasicare	MeSH
Flukare	MeSH
Tremacide	MeSH
6-chloro-5-(2,3-Dichlorophenoxy)-2-methylsulphanyl-1H-benzimidazole	Generator
Virbac brand OF triclabendazole	MeSH
Triclabendazole	MeSH
Jurox brand OF triclabendazole	MeSH
Novartis brand OF triclabendazole	MeSH
6-Chloro-5-(2,3-dichlorophenoxy)-2-(methylsulphanyl)-1H-1,3-benzodiazole	Generator

Chemical Formula

C₁₄H₉Cl₃N₂OS

Average Molecular Weight

359.65

Monoisotopic Molecular Weight

357.9501172

IUPAC Name

6-chloro-5-(2,3-dichlorophenoxy)-2-(methylsulfanyl)-1H-1,3-benzodiazole

Traditional Name

triclabendazole

CAS Registry Number

Not Available

SMILES

CSC1=NC2=C(N1)C=C(Cl)C(OC1=CC=CC(Cl)=C1Cl)=C2

InChI Identifier

InChI=1S/C14H9Cl3N2OS/c1-21-14-18-9-5-8(16)12(6-10(9)19-14)20-11-4-2-3-7(15)13(11)17/h2-6H,1H3,(H,18,19)

InChI Key

NQPDXQQQCQDHHW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Diarylethers

Alternative Parents

Substituents

Diaryl ether
Benzimidazole
Phenoxy compound
Aryl thioether
Phenol ether
1,2-dichlorobenzene
Alkylarylthioether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Azole
Heteroaromatic compound
Imidazole
Azacycle
Organoheterocyclic compound
Sulfenyl compound
Thioether
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organosulfur compound
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	5.5	ALOGPS
logP	5.88	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	10.46	ChemAxon
pKa (Strongest Basic)	4.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.86 m³·mol⁻¹	ChemAxon
Polarizability	34.02 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	171.262	30932474
DeepCCS	[M-H]-	168.904	30932474
DeepCCS	[M-2H]-	202.048	30932474
DeepCCS	[M+Na]+	177.355	30932474
AllCCS	[M+H]+	171.4	32859911
AllCCS	[M+H-H2O]+	168.4	32859911
AllCCS	[M+NH4]+	174.2	32859911
AllCCS	[M+Na]+	175.0	32859911
AllCCS	[M-H]-	151.9	32859911
AllCCS	[M+Na-2H]-	150.6	32859911
AllCCS	[M+HCOO]-	149.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Triclabendazole	CSC1=NC2=C(N1)C=C(Cl)C(OC1=CC=CC(Cl)=C1Cl)=C2	3923.6	Standard polar	33892256
Triclabendazole	CSC1=NC2=C(N1)C=C(Cl)C(OC1=CC=CC(Cl)=C1Cl)=C2	2940.6	Standard non polar	33892256
Triclabendazole	CSC1=NC2=C(N1)C=C(Cl)C(OC1=CC=CC(Cl)=C1Cl)=C2	3024.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Triclabendazole,1TMS,isomer #1	CSC1=NC2=CC(OC3=CC=CC(Cl)=C3Cl)=C(Cl)C=C2N1[Si](C)(C)C	3071.1	Semi standard non polar	33892256
Triclabendazole,1TMS,isomer #1	CSC1=NC2=CC(OC3=CC=CC(Cl)=C3Cl)=C(Cl)C=C2N1[Si](C)(C)C	2688.4	Standard non polar	33892256
Triclabendazole,1TMS,isomer #1	CSC1=NC2=CC(OC3=CC=CC(Cl)=C3Cl)=C(Cl)C=C2N1[Si](C)(C)C	3673.9	Standard polar	33892256
Triclabendazole,1TBDMS,isomer #1	CSC1=NC2=CC(OC3=CC=CC(Cl)=C3Cl)=C(Cl)C=C2N1[Si](C)(C)C(C)(C)C	3260.5	Semi standard non polar	33892256
Triclabendazole,1TBDMS,isomer #1	CSC1=NC2=CC(OC3=CC=CC(Cl)=C3Cl)=C(Cl)C=C2N1[Si](C)(C)C(C)(C)C	2921.9	Standard non polar	33892256
Triclabendazole,1TBDMS,isomer #1	CSC1=NC2=CC(OC3=CC=CC(Cl)=C3Cl)=C(Cl)C=C2N1[Si](C)(C)C(C)(C)C	3661.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Triclabendazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0230-1944000000-0558457f41742a7d656b	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triclabendazole 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 - Triclabendazole LC-ESI-qTof , Positive-QTOF	splash10-004i-0209000000-8ccc98a85688a2a0d3da	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QTOF , negative-QTOF	splash10-0002-0900000000-3fbd7829350b3af433e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QTOF , negative-QTOF	splash10-0002-0900000000-2fb79bfda8b99fe8585c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QTOF , negative-QTOF	splash10-0002-0900000000-94c576ac00ee61093edc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QTOF , negative-QTOF	splash10-0002-0900000000-d7b2f78bf0528ede0828	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QTOF , negative-QTOF	splash10-0002-0900000000-4e1a783d7691ad4bd8e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QFT , negative-QTOF	splash10-0a4i-0009000000-7f1cc56aaa6613e8fe57	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QFT , negative-QTOF	splash10-0a4i-0009000000-e6fec3ad89cc5d90283b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QFT , negative-QTOF	splash10-0005-0936000000-920cfafffb0d59c0929a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QFT , negative-QTOF	splash10-0002-0900000000-7c1864f299cbfbfaf0d4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QFT , negative-QTOF	splash10-0002-1900000000-e79f0dad86cbb7cb4483	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QFT , negative-QTOF	splash10-0002-3900000000-79b4e72d8d6c11ae38cd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QFT , negative-QTOF	splash10-066r-9000000000-6ef46d3a6eaad77f377a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QFT , negative-QTOF	splash10-066r-9000000000-0143c04bcc788d3bacc1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QFT , negative-QTOF	splash10-066r-9000000000-ec03c59296086f67e89a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QTOF , positive-QTOF	splash10-0bt9-0019000000-8d8f52e04ea79bdcc664	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QTOF , positive-QTOF	splash10-00dl-0396000000-bbdca10dffc2975f73b5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QTOF , positive-QTOF	splash10-00di-0390000000-19e15a4b196227bf4cd1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Triclabendazole LC-ESI-QFT , positive-QTOF	splash10-0a4i-0009000000-1c6e57328ce0ce9875db	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclabendazole 10V, Positive-QTOF	splash10-0a4i-0009000000-fa35ea94dbfe52339d64	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclabendazole 20V, Positive-QTOF	splash10-0a4i-1009000000-f1c2fd4280791a245c9f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclabendazole 40V, Positive-QTOF	splash10-0002-9412000000-3f049c0a597d3add7509	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclabendazole 10V, Negative-QTOF	splash10-0a4i-0009000000-a021a50522b671d8a3a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclabendazole 20V, Negative-QTOF	splash10-0a4l-1009000000-9e98e0b7ca624d2c1716	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triclabendazole 40V, Negative-QTOF	splash10-03dl-5595000000-a17da5226a34443eca47	2016-08-03	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

DB12245

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

45565

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triclabendazole

METLIN ID

Not Available

PubChem Compound

50248

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

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 Triclabendazole (HMDB0259181)

MOL for HMDB0259181 (Triclabendazole)

3D MOL for HMDB0259181 (Triclabendazole)

3D SDF for HMDB0259181 (Triclabendazole)

3D-SDF for HMDB0259181 (Triclabendazole)

PDB for HMDB0259181 (Triclabendazole)

3D PDB for HMDB0259181 (Triclabendazole)

SMILES for HMDB0259181 (Triclabendazole)

INCHI for HMDB0259181 (Triclabendazole)

Structure for HMDB0259181 (Triclabendazole)

3D Structure for HMDB0259181 (Triclabendazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra