Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:04 UTC

HMDB ID

HMDB0015679

Secondary Accession Numbers

HMDB15679

Metabolite Identification

Common Name

Niclosamide

Description

Niclosamide, also known as niclocide or fenasal, belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene. They are an even greater problem in domestic animals. Niclosamide is a drug which is used for the treatment of tapeworm and intestinal fluke infections: taenia saginata (beef tapeworm), taenia solium (pork tapeworm), diphyllobothrium latum (fish tapeworm), fasciolopsis buski (large intestinal fluke). niclosamide is also used as a molluscicide in the control of schistosomiasis. Niclosamide is an extremely weak basic (essentially neutral) compound (based on its pKa). Niclosamide works by killing tapeworms on contact. Niclosamide is a potentially toxic compound. Helminths (worms) are multicellular organisms that infect very large numbers of humans and cause a broad range of diseases. Adult worms (but not ova) are rapidly killed, presumably due to uncoupling of oxidative phosphorylation or stimulation of ATPase activity. Over 1 billion people are infected with intestinal nematodes, and many millions are infected with filarial nematodes, flukes, and tapeworms.

Structure

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

HMDB0015679
     RDKit          3D
Niclosamide
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.6230    1.1194    1.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089    0.3889    0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885   -0.2502   -0.3195 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962   -0.1548   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.5798    0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4711    0.5900    0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2928   -0.1061    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6886   -0.0652    0.2523 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.2112    0.6162    1.1685 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5259   -0.7435   -0.5795 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.6841   -0.8346   -0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3212   -0.8536   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6435   -1.8353   -2.2873 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    0.2048    0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.5973   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0671   -0.8008   -1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4479   -1.8299   -2.6396 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0468   -0.1866   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6701    0.6026    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306    0.8254    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0839    1.6330    1.9378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1883   -0.8671   -1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069    1.1452    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007    1.1933    1.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3120   -1.3924   -1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9594   -1.0847   -1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1084   -0.3109   -0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518    1.0968    1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    1.9173    2.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
  2 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 12  4  1  0
 20 14  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
 11 25  1  0
 15 26  1  0
 18 27  1  0
 19 28  1  0
 21 29  1  0
M  CHG  2   8   1  10  -1
M  END


  Mrv0541 02241214202D          

 21 22  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   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
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 21  1  0  0  0  0
M  CHG  2   7   1   9  -1
M  END
> <DATABASE_ID>
HMDB0015679

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(C=C(Cl)C=C1)C(=O)NC1=C(Cl)C=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H8Cl2N2O4/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15/h1-6,18H,(H,16,19)

> <INCHI_KEY>
RJMUSRYZPJIFPJ-UHFFFAOYSA-N

> <FORMULA>
C13H8Cl2N2O4

> <MOLECULAR_WEIGHT>
327.12

> <EXACT_MASS>
325.986112168

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.472141785819964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide

> <ALOGPS_LOGP>
4.49

> <JCHEM_LOGP>
3.9096388419999997

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.64694026799149

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.8869995484430495

> <JCHEM_PKA_STRONGEST_BASIC>
-4.411725750858949

> <JCHEM_POLAR_SURFACE_AREA>
95.15

> <JCHEM_REFRACTIVITY>
80.50670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.99e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
niclosamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015679
     RDKit          3D
Niclosamide
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.6230    1.1194    1.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089    0.3889    0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885   -0.2502   -0.3195 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962   -0.1548   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.5798    0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4711    0.5900    0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2928   -0.1061    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6886   -0.0652    0.2523 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.2112    0.6162    1.1685 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5259   -0.7435   -0.5795 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.6841   -0.8346   -0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3212   -0.8536   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6435   -1.8353   -2.2873 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    0.2048    0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.5973   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0671   -0.8008   -1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4479   -1.8299   -2.6396 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0468   -0.1866   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6701    0.6026    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306    0.8254    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0839    1.6330    1.9378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1883   -0.8671   -1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069    1.1452    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007    1.1933    1.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3120   -1.3924   -1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9594   -1.0847   -1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1084   -0.3109   -0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518    1.0968    1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    1.9173    2.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
  2 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 12  4  1  0
 20 14  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
 11 25  1  0
 15 26  1  0
 18 27  1  0
 19 28  1  0
 21 29  1  0
M  CHG  2   8   1  10  -1
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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+1
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O-1
HETATM   10 Cl   UNK     0       0.000  -7.700   0.000  0.00  0.00          Cl+0
HETATM   11  N   UNK     0       2.667  -9.240   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       1.334 -14.630   0.000  0.00  0.00          Cl+0
HETATM   21  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4                                                            
CONECT   11    3   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18                                                            
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0015679
HETATM    1  O1  UNL     1      -0.623   1.119   1.417  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.909   0.389   0.451  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.088  -0.250  -0.319  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.496  -0.155  -0.112  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.093   0.580   0.878  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.471   0.590   0.972  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.293  -0.106   0.117  1.00  0.00           C  
HETATM    8  N2  UNL     1       5.689  -0.065   0.252  1.00  0.00           N1+
HETATM    9  O2  UNL     1       6.211   0.616   1.168  1.00  0.00           O  
HETATM   10  O3  UNL     1       6.526  -0.744  -0.579  1.00  0.00           O1-
HETATM   11  C6  UNL     1       3.684  -0.835  -0.866  1.00  0.00           C  
HETATM   12  C7  UNL     1       2.321  -0.854  -0.971  1.00  0.00           C  
HETATM   13 CL1  UNL     1       1.643  -1.835  -2.287  1.00  0.00          CL  
HETATM   14  C8  UNL     1      -2.330   0.205   0.128  1.00  0.00           C  
HETATM   15  C9  UNL     1      -2.740  -0.597  -0.938  1.00  0.00           C  
HETATM   16  C10 UNL     1      -4.067  -0.801  -1.281  1.00  0.00           C  
HETATM   17 CL2  UNL     1      -4.448  -1.830  -2.640  1.00  0.00          CL  
HETATM   18  C11 UNL     1      -5.047  -0.187  -0.541  1.00  0.00           C  
HETATM   19  C12 UNL     1      -4.670   0.603   0.506  1.00  0.00           C  
HETATM   20  C13 UNL     1      -3.331   0.825   0.875  1.00  0.00           C  
HETATM   21  O4  UNL     1      -3.084   1.633   1.938  1.00  0.00           O  
HETATM   22  H1  UNL     1      -0.188  -0.867  -1.137  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.507   1.145   1.578  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.901   1.193   1.782  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.312  -1.392  -1.554  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.959  -1.085  -1.524  1.00  0.00           H  
HETATM   27  H6  UNL     1      -6.108  -0.311  -0.766  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.452   1.097   1.101  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.279   1.917   2.355  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   14
CONECT    3    4   22
CONECT    4    5    5   12
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   11   12   12   25
CONECT   12   13
CONECT   14   15   15   20
CONECT   15   16   26
CONECT   16   17   18   18
CONECT   18   19   27
CONECT   19   20   20   28
CONECT   20   21
CONECT   21   29
END

HMDB0015679
     RDKit          3D
Niclosamide
 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.6230    1.1194    1.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9089    0.3889    0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885   -0.2502   -0.3195 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962   -0.1548   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.5798    0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4711    0.5900    0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2928   -0.1061    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6886   -0.0652    0.2523 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.2112    0.6162    1.1685 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5259   -0.7435   -0.5795 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.6841   -0.8346   -0.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3212   -0.8536   -0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6435   -1.8353   -2.2873 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    0.2048    0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.5973   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0671   -0.8008   -1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4479   -1.8299   -2.6396 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0468   -0.1866   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6701    0.6026    0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3306    0.8254    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0839    1.6330    1.9378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1883   -0.8671   -1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069    1.1452    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007    1.1933    1.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3120   -1.3924   -1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9594   -1.0847   -1.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1084   -0.3109   -0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4518    1.0968    1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    1.9173    2.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
  2 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 12  4  1  0
 20 14  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
 11 25  1  0
 15 26  1  0
 18 27  1  0
 19 28  1  0
 21 29  1  0
M  CHG  2   8   1  10  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Niclocide	Kegg
Aventis brand OF niclosamide	HMDB
Bayer brand OF niclosamide	HMDB
Fenasal	HMDB
Bayer 73	HMDB
Bayluscide	HMDB
Clonitralide	HMDB
Yomesan	HMDB
Bayer 2353	HMDB
Niclosamide, 2-aminoethanol (1:1)	HMDB
Phenasal	HMDB
Radewerm	HMDB
Trédémine	HMDB

Chemical Formula

C₁₃H₈Cl₂N₂O₄

Average Molecular Weight

327.12

Monoisotopic Molecular Weight

325.986112168

IUPAC Name

5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide

Traditional Name

niclosamide

CAS Registry Number

50-65-7

SMILES

OC1=C(C=C(Cl)C=C1)C(=O)NC1=C(Cl)C=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C13H8Cl2N2O4/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15/h1-6,18H,(H,16,19)

InChI Key

RJMUSRYZPJIFPJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Benzanilides

Alternative Parents

Substituents

Benzanilide
Salicylamide
Salicylic acid or derivatives
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Nitrobenzene
Nitroaromatic compound
Benzoyl
4-halophenol
4-chlorophenol
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Phenol
Aryl chloride
Aryl halide
Vinylogous acid
Secondary carboxylic acid amide
Organic nitro compound
Carboxamide group
C-nitro compound
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboxylic acid derivative
Organic oxoazanium
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organohalogen compound
Organochloride
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic zwitterion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015679)
Membrane (HMDB: HMDB0015679)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.008 g/L	ALOGPS
logP	4.49	ALOGPS
logP	3.91	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	6.89	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.51 m³·mol⁻¹	ChemAxon
Polarizability	28.47 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]+	167.336	30932474
DeepCCS	[M-H]-	164.978	30932474
DeepCCS	[M-2H]-	198.578	30932474
DeepCCS	[M+Na]+	174.743	30932474
AllCCS	[M+H]+	165.7	32859911
AllCCS	[M+H-H2O]+	162.4	32859911
AllCCS	[M+NH4]+	168.7	32859911
AllCCS	[M+Na]+	169.6	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	157.8	32859911
AllCCS	[M+HCOO]-	156.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Niclosamide	OC1=C(C=C(Cl)C=C1)C(=O)NC1=C(Cl)C=C(C=C1)[N+]([O-])=O	4312.3	Standard polar	33892256
Niclosamide	OC1=C(C=C(Cl)C=C1)C(=O)NC1=C(Cl)C=C(C=C1)[N+]([O-])=O	2761.0	Standard non polar	33892256
Niclosamide	OC1=C(C=C(Cl)C=C1)C(=O)NC1=C(Cl)C=C(C=C1)[N+]([O-])=O	2820.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Niclosamide,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+](=O)[O-])C=C1Cl	2892.3	Semi standard non polar	33892256
Niclosamide,1TMS,isomer #2	C[Si](C)(C)N(C(=O)C1=CC(Cl)=CC=C1O)C1=CC=C([N+](=O)[O-])C=C1Cl	2622.7	Semi standard non polar	33892256
Niclosamide,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C	2615.5	Semi standard non polar	33892256
Niclosamide,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C	2683.0	Standard non polar	33892256
Niclosamide,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C	3175.4	Standard polar	33892256
Niclosamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+](=O)[O-])C=C1Cl	3149.5	Semi standard non polar	33892256
Niclosamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC(Cl)=CC=C1O)C1=CC=C([N+](=O)[O-])C=C1Cl	2886.7	Semi standard non polar	33892256
Niclosamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C(C)(C)C	3157.2	Semi standard non polar	33892256
Niclosamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C(C)(C)C	3128.2	Standard non polar	33892256
Niclosamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C(C)(C)C	3315.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Niclosamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-6901000000-2b365b023e021b160f32	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Niclosamide GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-8930000000-69bd67a318e9efd73dde	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Niclosamide 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 - Niclosamide LC-ESI-qTof , Positive-QTOF	splash10-0006-2920000000-abe97627fbae89daa0db	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOF	splash10-00di-0029000000-07d09d3c05d206cf1709	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOF	splash10-00dr-0982000000-be44b0c8755c752ba0f3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOF	splash10-00di-0910000000-4aa0326731fc70d171de	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOF	splash10-00di-0900000000-d166a8246615e944705a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOF	splash10-00di-0900000000-8da8fb85b28f330b445d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOF	splash10-0abi-0900000000-10c251c2f1c5006a7f25	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOF	splash10-0fka-5952000000-25e2c37ca8eb59d1db22	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOF	splash10-0002-9200000000-57c28b8b2b3dc926256d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOF	splash10-0002-9100000000-2b567071c6cfa78ecf55	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOF	splash10-0002-9100000000-33d3827b1d5b1d8b0dd1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOF	splash10-0002-9000000000-9cee7be3f0ec47a2cf6e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOF	splash10-0002-9000000000-cf3d1288bd0150e477be	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide , positive-QTOF	splash10-004i-0519000000-8dd141b868e2002a2bfa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide , positive-QTOF	splash10-0udi-4900000000-d83bc5ee9b78c460078c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide 60V, Negative-QTOF	splash10-00di-0900000000-1c2167607d05b47594fb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide 75V, Negative-QTOF	splash10-00di-0900000000-25ef559cdcba657ec7bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide 45V, Negative-QTOF	splash10-00di-0910000000-137a6a40379842639b2a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Niclosamide 30V, Negative-QTOF	splash10-00dr-0982000000-c63ef31f0e3de2dbbbd1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niclosamide 10V, Positive-QTOF	splash10-004i-0009000000-19d348ccf2b61b75bf34	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niclosamide 20V, Positive-QTOF	splash10-004i-0009000000-7d6ea94b8683b59260b8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niclosamide 40V, Positive-QTOF	splash10-056r-0639000000-2cc47cc1fb3e56e9be10	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niclosamide 10V, Negative-QTOF	splash10-00di-0009000000-720f5eedf2a446e4de88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niclosamide 20V, Negative-QTOF	splash10-00di-0009000000-9146e1b30ee98c36f42b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niclosamide 40V, Negative-QTOF	splash10-05bf-6629000000-77e8ecb80b64e657ec0f	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06803	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06803	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06803

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4322

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Niclosamide

METLIN ID

Not Available

PubChem Compound

4477

PDB ID

Not Available

ChEBI ID

478218

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

(). 2010. Detailed Drug Information for the ConsumerÃ¢â€žÂ¢. Greenwood Village, CO. Thomson Reuters. ISBN-10: 1-56363-575-5. ISSN: 0740-4174. STAT!Ref Online Electronic Medical Library.. .
Clinical Pharmacology of the Antihelminthic Drugs Chapter 53). Katzung BG: Basic & Clinical Pharmacology, 12th edition [Link]

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Bapiro TE, Egnell AC, Hasler JA, Masimirembwa CM: Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5. [PubMed:11124226 ]

Enzyme Details

2. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Bapiro TE, Egnell AC, Hasler JA, Masimirembwa CM: Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5. [PubMed:11124226 ]

Showing metabocard for Niclosamide (HMDB0015679)

MOL for HMDB0015679 (Niclosamide)

3D MOL for HMDB0015679 (Niclosamide)

3D SDF for HMDB0015679 (Niclosamide)

3D-SDF for HMDB0015679 (Niclosamide)

PDB for HMDB0015679 (Niclosamide)

3D PDB for HMDB0015679 (Niclosamide)

SMILES for HMDB0015679 (Niclosamide)

INCHI for HMDB0015679 (Niclosamide)

Structure for HMDB0015679 (Niclosamide)

3D Structure for HMDB0015679 (Niclosamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References