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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:22 UTC

Update Date

2022-03-07 02:52:16 UTC

HMDB ID

HMDB0029745

Secondary Accession Numbers

HMDB29745

Metabolite Identification

Common Name

Fenbendazole

Description

Veterinary anthelmintic. Fenbendazole is a fda approved for use in cattle, pigs and goats Fenbendazole (Hoechst brand names Panacur and Safe-Guard, Intervet Panacur and Panacur Rabbit) is a broad spectrum benzimidazole anthelmintic used against gastrointestinal parasites including roundworms, hookworms, whipworms, the taenia species of tapeworms, pinworms, aelurostrongylus, paragonimiasis, strongyles and strongyloides and can be administered to sheep, cattle, horses, fish, dogs, cats, rabbits and seals. Drug interactions may occur if using bromsalan flukicides (Dibromsalan, Tribromsalan). Abortions in cattle and death in sheep have been reported after using these medications together. (Plumb's Veterinary Drug Handbook, Fifth Edition. 2005

Structure

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

HMDB0029745
     RDKit          3D
Fenbendazole
 34 36  0  0  0  0  0  0  0  0999 V2000
    7.3422    1.5633    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0980    2.0437   -0.2531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9767    1.1964   -0.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919    0.0307    0.1334 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7476    1.7267   -0.6823 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5779    0.9331   -0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401    1.3789   -1.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4570    0.3785   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    0.2593   -1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5811   -0.9290   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3309   -1.1085   -1.4256 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -0.7233   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645    0.5678    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5322    0.8523    1.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963   -0.0990    2.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4519   -1.3863    2.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6821   -1.6843    0.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8547   -2.0009   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -1.8811   -0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806   -0.6880   -0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4836   -0.3508   -0.3563 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3214    0.4976    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7184    2.1752    1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0873    1.6398   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6910    2.7223   -0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436    1.1140   -1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4802    1.3275   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8820    1.8722    1.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5019    0.1247    3.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7169   -2.1662    2.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3241   -2.6999    0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3498   -2.9428   -0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862   -2.7162    0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228   -1.0276    0.0053 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  6  1  0
 20  8  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  9 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
M  END

  Mrv0541 02241214542D          

 21 23  0  0  0  0            999 V2000
    0.0003   -2.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1615   -3.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041   -3.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138   -3.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3758   -2.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086   -2.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9706   -1.3354    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3235   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4854   -1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519   -0.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900    0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810    0.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810    1.3354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900    1.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333    2.3878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5668    2.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2422    2.7923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7281    3.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4847   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900    3.7640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3758    0.9303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 19  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 21  1  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029745

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H13N3O2S/c1-20-15(19)18-14-16-12-8-7-11(9-13(12)17-14)21-10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19)

> <INCHI_KEY>
HDDSHPAODJUKPD-UHFFFAOYSA-N

> <FORMULA>
C15H13N3O2S

> <MOLECULAR_WEIGHT>
299.348

> <EXACT_MASS>
299.072847365

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.756402899475134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl N-[5-(phenylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
3.9895049709999997

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.94348238381934

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.585539982696433

> <JCHEM_PKA_STRONGEST_BASIC>
4.05804040004986

> <JCHEM_POLAR_SURFACE_AREA>
67.01

> <JCHEM_REFRACTIVITY>
83.61250000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.09e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fenbendazole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029745
     RDKit          3D
Fenbendazole
 34 36  0  0  0  0  0  0  0  0999 V2000
    7.3422    1.5633    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0980    2.0437   -0.2531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9767    1.1964   -0.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919    0.0307    0.1334 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7476    1.7267   -0.6823 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5779    0.9331   -0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401    1.3789   -1.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4570    0.3785   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    0.2593   -1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5811   -0.9290   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3309   -1.1085   -1.4256 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -0.7233   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645    0.5678    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5322    0.8523    1.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963   -0.0990    2.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4519   -1.3863    2.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6821   -1.6843    0.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8547   -2.0009   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -1.8811   -0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806   -0.6880   -0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4836   -0.3508   -0.3563 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3214    0.4976    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7184    2.1752    1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0873    1.6398   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6910    2.7223   -0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436    1.1140   -1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4802    1.3275   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8820    1.8722    1.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5019    0.1247    3.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7169   -2.1662    2.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3241   -2.6999    0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3498   -2.9428   -0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862   -2.7162    0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228   -1.0276    0.0053 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  6  1  0
 20  8  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  9 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.001  -4.457   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.301  -5.967   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.754  -7.026   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.266  -6.572   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.568  -5.062   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.509  -4.003   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      -1.812  -2.493   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0      -0.604  -1.436   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.906  -1.888   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.963  -0.981   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.661   0.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.151   0.981   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.151   2.493   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.661   2.946   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.115   4.457   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.058   5.515   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.452   5.212   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.359   6.421   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.905  -0.076   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.661   7.026   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       2.568   1.736   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    8   12                                                       
CONECT   20   16                                                            
CONECT   21   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0029745
HETATM    1  C1  UNL     1       7.342   1.563   0.163  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.098   2.044  -0.253  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.977   1.196  -0.255  1.00  0.00           C  
HETATM    4  O2  UNL     1       5.192   0.031   0.133  1.00  0.00           O  
HETATM    5  N1  UNL     1       3.748   1.727  -0.682  1.00  0.00           N  
HETATM    6  C3  UNL     1       2.578   0.933  -0.710  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.340   1.379  -1.115  1.00  0.00           N  
HETATM    8  C4  UNL     1       0.457   0.378  -1.019  1.00  0.00           C  
HETATM    9  C5  UNL     1      -0.911   0.259  -1.288  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.581  -0.929  -1.090  1.00  0.00           C  
HETATM   11  S1  UNL     1      -3.331  -1.109  -1.426  1.00  0.00           S  
HETATM   12  C7  UNL     1      -4.323  -0.723  -0.003  1.00  0.00           C  
HETATM   13  C8  UNL     1      -4.765   0.568   0.213  1.00  0.00           C  
HETATM   14  C9  UNL     1      -5.532   0.852   1.319  1.00  0.00           C  
HETATM   15  C10 UNL     1      -5.896  -0.099   2.248  1.00  0.00           C  
HETATM   16  C11 UNL     1      -5.452  -1.386   2.025  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.682  -1.684   0.921  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.855  -2.001  -0.616  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.504  -1.881  -0.349  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.181  -0.688  -0.547  1.00  0.00           C  
HETATM   21  N3  UNL     1       2.484  -0.351  -0.356  1.00  0.00           N  
HETATM   22  H1  UNL     1       7.321   0.498   0.473  1.00  0.00           H  
HETATM   23  H2  UNL     1       7.718   2.175   1.007  1.00  0.00           H  
HETATM   24  H3  UNL     1       8.087   1.640  -0.645  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.691   2.722  -0.985  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.444   1.114  -1.656  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.480   1.327  -0.519  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.882   1.872   1.491  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.502   0.125   3.120  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.717  -2.166   2.734  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.324  -2.700   0.734  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.350  -2.943  -0.450  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.086  -2.716   0.024  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.223  -1.028   0.005  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   25
CONECT    6    7    7   21
CONECT    7    8
CONECT    8    9    9   20
CONECT    9   10   26
CONECT   10   11   18   18
CONECT   11   12
CONECT   12   13   13   17
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   16   29
CONECT   16   17   17   30
CONECT   17   31
CONECT   18   19   32
CONECT   19   20   20   33
CONECT   20   21
CONECT   21   34
END

HMDB0029745
     RDKit          3D
Fenbendazole
 34 36  0  0  0  0  0  0  0  0999 V2000
    7.3422    1.5633    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0980    2.0437   -0.2531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9767    1.1964   -0.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919    0.0307    0.1334 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7476    1.7267   -0.6823 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5779    0.9331   -0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401    1.3789   -1.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4570    0.3785   -1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115    0.2593   -1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5811   -0.9290   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3309   -1.1085   -1.4256 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -0.7233   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645    0.5678    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5322    0.8523    1.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963   -0.0990    2.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4519   -1.3863    2.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6821   -1.6843    0.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8547   -2.0009   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -1.8811   -0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1806   -0.6880   -0.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4836   -0.3508   -0.3563 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3214    0.4976    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7184    2.1752    1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0873    1.6398   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6910    2.7223   -0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436    1.1140   -1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4802    1.3275   -0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8820    1.8722    1.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5019    0.1247    3.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7169   -2.1662    2.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3241   -2.6999    0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3498   -2.9428   -0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862   -2.7162    0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228   -1.0276    0.0053 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  6  1  0
 20  8  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  9 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(Methoxycarbonylamino)-5-(phenylthio)benzimidazole	ChEBI
5-(Phenylthio)-2-benzimidazolecarbamic acid methyl ester	ChEBI
[5-(Phenylthio)-1H-benzimidazol-2-yl]carbamic acid methyl ester	ChEBI
Fenbendazol	ChEBI
Fenbendazolum	ChEBI
Hoe 881V	ChEBI
Methyl 5-(phenylthio)-2-benzimidazolecarbamate	ChEBI
Methyl [5-(phenylthio)-1H-benzimidazol-2-yl]carbamate	ChEBI
Panacur	ChEBI
Safe-quard	ChEBI
5-(Phenylthio)-2-benzimidazolecarbamate methyl ester	Generator
[5-(Phenylthio)-1H-benzimidazol-2-yl]carbamate methyl ester	Generator
Methyl 5-(phenylthio)-2-benzimidazolecarbamic acid	Generator
Methyl [5-(phenylthio)-1H-benzimidazol-2-yl]carbamic acid	Generator
2-Benzimidazolecarbamic acid, 5-(phenylthio)-, methyl ester	HMDB
Axilur	HMDB
Hoe 881	HMDB
Methyl (5-(phenylthio)-1H-benzimidazol-2-yl)carbamate	HMDB
Methyl 5-phenylthio-1H-benzimidazol-2-ylcarbamate	HMDB
Methyl [5-(phenylsulfanyl)-1H-benzimidazol-2-yl]carbamate	HMDB
Pancacur	HMDB
Phenbendasol	HMDB
Safe-guard	HMDB
Worm-a-rest	HMDB

Chemical Formula

C₁₅H₁₃N₃O₂S

Average Molecular Weight

299.348

Monoisotopic Molecular Weight

299.072847365

IUPAC Name

methyl N-[5-(phenylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate

Traditional Name

fenbendazole

CAS Registry Number

43210-67-9

SMILES

COC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C2

InChI Identifier

InChI=1S/C15H13N3O2S/c1-20-15(19)18-14-16-12-8-7-11(9-13(12)17-14)21-10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19)

InChI Key

HDDSHPAODJUKPD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

2-benzimidazolylcarbamic acid esters

Direct Parent

2-benzimidazolylcarbamic acid esters

Alternative Parents

Substituents

2-benzimidazolylcarbamic acid ester
Diarylthioether
Aryl thioether
Thiophenol ether
Monocyclic benzene moiety
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Carbamic acid ester
Carbonic acid derivative
Thioether
Azacycle
Sulfenyl compound
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:77092 )
organic sulfide (CHEBI:77092 )
benzimidazoles (CHEBI:77092 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029745)
Cell membrane (HMDB: HMDB0029745)

Source

Exogenous

Exogenous (HMDB: HMDB0029745)

Food

Food (HMDB: HMDB0029745)

Endogenous

Endogenous (HMDB: HMDB0029745)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0029745)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	233 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	170.835	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000954

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0061 g/L	ALOGPS
logP	3.33	ALOGPS
logP	3.99	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.59	ChemAxon
pKa (Strongest Basic)	4.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.01 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.61 m³·mol⁻¹	ChemAxon
Polarizability	31.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	172.073	31661259
DarkChem	[M-H]-	171.746	31661259
DeepCCS	[M+H]+	169.328	30932474
DeepCCS	[M-H]-	166.97	30932474
DeepCCS	[M-2H]-	199.857	30932474
DeepCCS	[M+Na]+	175.422	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.7	32859911
AllCCS	[M+NH4]+	170.0	32859911
AllCCS	[M+Na]+	170.9	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	166.0	32859911
AllCCS	[M+HCOO]-	164.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fenbendazole	COC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C2	3774.7	Standard polar	33892256
Fenbendazole	COC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C2	2523.5	Standard non polar	33892256
Fenbendazole	COC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C2	3067.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fenbendazole,1TMS,isomer #1	COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2[NH]1)[Si](C)(C)C	2747.9	Semi standard non polar	33892256
Fenbendazole,1TMS,isomer #1	COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2[NH]1)[Si](C)(C)C	2630.0	Standard non polar	33892256
Fenbendazole,1TMS,isomer #2	COC(=O)NC1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C	2795.1	Semi standard non polar	33892256
Fenbendazole,1TMS,isomer #2	COC(=O)NC1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C	2542.7	Standard non polar	33892256
Fenbendazole,2TMS,isomer #1	COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C)[Si](C)(C)C	2773.1	Semi standard non polar	33892256
Fenbendazole,2TMS,isomer #1	COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C)[Si](C)(C)C	2640.0	Standard non polar	33892256
Fenbendazole,1TBDMS,isomer #1	COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2[NH]1)[Si](C)(C)C(C)(C)C	2930.3	Semi standard non polar	33892256
Fenbendazole,1TBDMS,isomer #1	COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2[NH]1)[Si](C)(C)C(C)(C)C	2835.0	Standard non polar	33892256
Fenbendazole,1TBDMS,isomer #2	COC(=O)NC1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C(C)(C)C	2994.4	Semi standard non polar	33892256
Fenbendazole,1TBDMS,isomer #2	COC(=O)NC1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C(C)(C)C	2773.9	Standard non polar	33892256
Fenbendazole,2TBDMS,isomer #1	COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3106.3	Semi standard non polar	33892256
Fenbendazole,2TBDMS,isomer #1	COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3032.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fenbendazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-1590000000-b1bdde740346b5e86169	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenbendazole 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 - Fenbendazole LC-ESI-QTOF , positive-QTOF	splash10-0udi-0009000000-c52f281023614ea62183	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOF	splash10-0gb9-0095000000-aaa3ee589638ab95694b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOF	splash10-014i-0190000000-542ec3d7c28deadb2a86	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOF	splash10-0aor-0950000000-ca845f292ef10ba06084	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0900000000-1a2be36ab88deab8ea4b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOF	splash10-0udi-0009000000-74437145eda13588d093	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOF	splash10-014i-0091000000-372a453c1125eba23231	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOF	splash10-066r-0790000000-d29f6f0177872af1decf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0900000000-772531394a7b47426d88	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOF	splash10-0a59-0900000000-14444c086a0cdeba7497	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole , positive-QTOF	splash10-066r-2950000000-c7869e27c483ff82b599	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole 50V, Positive-QTOF	splash10-0a4i-0900000000-399f6be99867d442c079	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole 50V, Positive-QTOF	splash10-0a59-0900000000-5907f0139e02ca29f43a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole 40V, Positive-QTOF	splash10-0a4i-0900000000-772531394a7b47426d88	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole 10V, Positive-QTOF	splash10-0udi-0009000000-c52f281023614ea62183	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole 20V, Positive-QTOF	splash10-0gb9-0095000000-aaa3ee589638ab95694b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole 40V, Positive-QTOF	splash10-0aor-0950000000-9c6037ec83f1156a6e89	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole 30V, Positive-QTOF	splash10-014i-0190000000-542ec3d7c28deadb2a86	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbendazole 20V, Positive-QTOF	splash10-014i-0091000000-372a453c1125eba23231	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbendazole 10V, Positive-QTOF	splash10-0udi-0269000000-1dbacf97c14ccb6e6d2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbendazole 20V, Positive-QTOF	splash10-00kf-0191000000-073f08323851b13a48c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbendazole 40V, Positive-QTOF	splash10-0a4i-2920000000-260a80378a37148914a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbendazole 10V, Negative-QTOF	splash10-066s-2090000000-eb8b842b3c805178f94e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbendazole 20V, Negative-QTOF	splash10-014i-2290000000-388e3fb832b0ad04f98d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbendazole 40V, Negative-QTOF	splash10-0a4i-1930000000-f2170079121987663840	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

DB11410

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000946

KNApSAcK ID

Not Available

Chemspider ID

3217

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fenbendazole

METLIN ID

Not Available

PubChem Compound

3334

PDB ID

Not Available

ChEBI ID

77092

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

Harcourt-Brown FM, Holloway HK: Encephalitozoon cuniculi in pet rabbits. Vet Rec. 2003 Apr 5;152(14):427-31. [PubMed:12708591 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Fenbendazole (HMDB0029745)

MOL for HMDB0029745 (Fenbendazole)

3D MOL for HMDB0029745 (Fenbendazole)

3D SDF for HMDB0029745 (Fenbendazole)

3D-SDF for HMDB0029745 (Fenbendazole)

PDB for HMDB0029745 (Fenbendazole)

3D PDB for HMDB0029745 (Fenbendazole)

SMILES for HMDB0029745 (Fenbendazole)

INCHI for HMDB0029745 (Fenbendazole)

Structure for HMDB0029745 (Fenbendazole)

3D Structure for HMDB0029745 (Fenbendazole)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra