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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

HMDB0015684

Secondary Accession Numbers

HMDB15684

Metabolite Identification

Common Name

Diloxanide

Description

Diloxanide, also known as furamide or entamide furoate, belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Diloxanide is a drug. Based on a literature review a significant number of articles have been published on Diloxanide.

Structure

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

HMDB0015684
     RDKit          3D
Diloxanide
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.9477   -0.4510    0.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2830   -0.0055   -0.3356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394    0.4462   -1.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4238    0.7994   -2.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5185    0.5334   -1.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1032    1.6942   -0.2229 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.2958   -1.0525   -1.2380 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -0.0560   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953    0.9177   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    0.8351   -0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261   -0.2269   -0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217   -0.3519   -0.2820 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0190    0.1935    0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3769    0.7750    1.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4698    0.1022    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3011   -0.5085   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5668   -0.3540    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4814    0.3389    1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2155    0.5812    1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1653   -1.2135    0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1920   -1.1094    0.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5953    0.1118    1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0430   -0.3363    0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7960   -1.5638    1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8548    0.9228   -2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5405    1.7514   -1.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930    1.6180   -1.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9459   -0.9980   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4456   -0.7297   -0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2942    0.6292    2.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387   -2.0469    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7649   -1.8955    0.7373 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
  5  7  1  0
  2  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 11 20  1  0
 20 21  2  0
 21  8  1  0
 19 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
 21 32  1  0
M  END

19529
  Mrv0541 02241214192D          

 21 22  0  0  0  0            999 V2000
    4.5079    3.7285    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    3.7285    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6970   -2.9439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.0785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    2.0785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319   -2.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -3.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2 16  1  0  0  0  0
  3 11  1  0  0  0  0
  3 18  1  0  0  0  0
  4 17  1  0  0  0  0
  4 21  1  0  0  0  0
  5 15  2  0  0  0  0
  6 18  2  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015684

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C(=O)C(Cl)Cl)C1=CC=C(OC(=O)C2=CC=CO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H11Cl2NO4/c1-17(13(18)12(15)16)9-4-6-10(7-5-9)21-14(19)11-3-2-8-20-11/h2-8,12H,1H3

> <INCHI_KEY>
BDYYDXJSHYEDGB-UHFFFAOYSA-N

> <FORMULA>
C14H11Cl2NO4

> <MOLECULAR_WEIGHT>
328.147

> <EXACT_MASS>
327.006513259

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.283715991093146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
3.0782326363333326

> <ALOGPS_LOGS>
-3.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.090932097864336

> <JCHEM_PKA_STRONGEST_BASIC>
-4.662713485474679

> <JCHEM_POLAR_SURFACE_AREA>
59.75

> <JCHEM_REFRACTIVITY>
78.2065

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diloxanide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015684
     RDKit          3D
Diloxanide
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.9477   -0.4510    0.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2830   -0.0055   -0.3356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394    0.4462   -1.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4238    0.7994   -2.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5185    0.5334   -1.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1032    1.6942   -0.2229 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.2958   -1.0525   -1.2380 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -0.0560   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953    0.9177   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    0.8351   -0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261   -0.2269   -0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217   -0.3519   -0.2820 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0190    0.1935    0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3769    0.7750    1.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4698    0.1022    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3011   -0.5085   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5668   -0.3540    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4814    0.3389    1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2155    0.5812    1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1653   -1.2135    0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1920   -1.1094    0.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5953    0.1118    1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0430   -0.3363    0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7960   -1.5638    1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8548    0.9228   -2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5405    1.7514   -1.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930    1.6180   -1.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9459   -0.9980   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4456   -0.7297   -0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2942    0.6292    2.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387   -2.0469    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7649   -1.8955    0.7373 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
  5  7  1  0
  2  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 11 20  1  0
 20 21  2  0
 21  8  1  0
 19 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
 21 32  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 19529                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Cl   UNK     0       8.415   6.960   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       5.747   6.960   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       5.747  -2.280   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.168  -5.495   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.415   3.880   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.080  -2.280   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       5.747   3.880   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.747   2.340   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   1.570   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   1.570   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747  -0.740   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   0.030   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   0.030   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   4.650   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   4.650   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   6.190   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -4.590   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -3.050   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.660  -5.495   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.184  -6.960   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.644  -6.960   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   11   18                                                       
CONECT    4   17   21                                                       
CONECT    5   15                                                            
CONECT    6   18                                                            
CONECT    7    8   14   15                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   12                                                       
CONECT   10    8   13                                                       
CONECT   11    3   12   13                                                  
CONECT   12    9   11                                                       
CONECT   13   10   11                                                       
CONECT   14    7                                                            
CONECT   15    5    7   16                                                  
CONECT   16    1    2   15                                                  
CONECT   17    4   18   19                                                  
CONECT   18    3    6   17                                                  
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21    4   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0015684
HETATM    1  C1  UNL     1      -3.948  -0.451   0.891  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.283  -0.005  -0.336  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.039   0.446  -1.437  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.424   0.799  -2.479  1.00  0.00           O  
HETATM    5  C3  UNL     1      -5.518   0.533  -1.447  1.00  0.00           C  
HETATM    6 CL1  UNL     1      -6.103   1.694  -0.223  1.00  0.00          CL  
HETATM    7 CL2  UNL     1      -6.296  -1.052  -1.238  1.00  0.00          CL  
HETATM    8  C4  UNL     1      -1.860  -0.056  -0.349  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.095   0.918  -0.951  1.00  0.00           C  
HETATM   10  C6  UNL     1       0.292   0.835  -0.939  1.00  0.00           C  
HETATM   11  C7  UNL     1       0.926  -0.227  -0.320  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.322  -0.352  -0.282  1.00  0.00           O  
HETATM   13  C8  UNL     1       3.019   0.193   0.792  1.00  0.00           C  
HETATM   14  O3  UNL     1       2.377   0.775   1.690  1.00  0.00           O  
HETATM   15  C9  UNL     1       4.470   0.102   0.891  1.00  0.00           C  
HETATM   16  C10 UNL     1       5.301  -0.509  -0.019  1.00  0.00           C  
HETATM   17  C11 UNL     1       6.567  -0.354   0.471  1.00  0.00           C  
HETATM   18  C12 UNL     1       6.481   0.339   1.653  1.00  0.00           C  
HETATM   19  O4  UNL     1       5.216   0.581   1.852  1.00  0.00           O  
HETATM   20  C13 UNL     1       0.165  -1.214   0.289  1.00  0.00           C  
HETATM   21  C14 UNL     1      -1.192  -1.109   0.263  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.595   0.112   1.782  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.043  -0.336   0.851  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.796  -1.564   1.028  1.00  0.00           H  
HETATM   25  H4  UNL     1      -5.855   0.923  -2.422  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.540   1.751  -1.441  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.893   1.618  -1.423  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.946  -0.998  -0.924  1.00  0.00           H  
HETATM   29  H8  UNL     1       7.446  -0.730  -0.031  1.00  0.00           H  
HETATM   30  H9  UNL     1       7.294   0.629   2.296  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.639  -2.047   0.774  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.765  -1.896   0.737  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    8
CONECT    3    4    4    5
CONECT    5    6    7   25
CONECT    8    9    9   21
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   12   20
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   16   19
CONECT   16   17   28
CONECT   17   18   18   29
CONECT   18   19   30
CONECT   20   21   21   31
CONECT   21   32
END

HMDB0015684
     RDKit          3D
Diloxanide
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.9477   -0.4510    0.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2830   -0.0055   -0.3356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394    0.4462   -1.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4238    0.7994   -2.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5185    0.5334   -1.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1032    1.6942   -0.2229 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.2958   -1.0525   -1.2380 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -0.0560   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953    0.9177   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    0.8351   -0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261   -0.2269   -0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217   -0.3519   -0.2820 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0190    0.1935    0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3769    0.7750    1.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4698    0.1022    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3011   -0.5085   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5668   -0.3540    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4814    0.3389    1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2155    0.5812    1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1653   -1.2135    0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1920   -1.1094    0.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5953    0.1118    1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0430   -0.3363    0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7960   -1.5638    1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8548    0.9228   -2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5405    1.7514   -1.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930    1.6180   -1.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9459   -0.9980   -0.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4456   -0.7297   -0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2942    0.6292    2.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387   -2.0469    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7649   -1.8955    0.7373 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
  5  7  1  0
  2  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 11 20  1  0
 20 21  2  0
 21  8  1  0
 19 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 20 31  1  0
 21 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8073 CB	ChEBI
Amebiazol	ChEBI
CB 8073	ChEBI
Dichlofurazol	ChEBI
Diclofurazol	ChEBI
Diloxanid furoate	ChEBI
Entamide furoate	ChEBI
Furamide	ChEBI
Furentomin	ChEBI
Histomibal	ChEBI
Miforon	ChEBI
Diloxanid furoic acid	Generator
Entamide furoic acid	Generator
Diloxanide furoate	HMDB
2-Furamide	HMDB
2,2-Dichloro-4'-hydroxy-N-methylacetanilide 2-furoate	HMDB
Diloxanide furoic acid	HMDB
4-(2,2-Dichloro-N-methylacetamido)phenyl furan-2-carboxylic acid	HMDB
Diloxanide	MeSH

Chemical Formula

C₁₄H₁₁Cl₂NO₄

Average Molecular Weight

328.147

Monoisotopic Molecular Weight

327.006513259

IUPAC Name

4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate

Traditional Name

diloxanide

CAS Registry Number

3736-81-0

SMILES

CN(C(=O)C(Cl)Cl)C1=CC=C(OC(=O)C2=CC=CO2)C=C1

InChI Identifier

InChI=1S/C14H11Cl2NO4/c1-17(13(18)12(15)16)9-4-6-10(7-5-9)21-14(19)11-3-2-8-20-11/h2-8,12H,1H3

InChI Key

BDYYDXJSHYEDGB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Furoic acid ester
Anilide
Furoic acid or derivatives
Phenoxy compound
Monocyclic benzene moiety
Furan
Tertiary carboxylic acid amide
Heteroaromatic compound
Carboxamide group
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Organochloride
Organohalogen compound
Organooxygen compound
Organic oxygen compound
Alkyl halide
Organopnictogen compound
Alkyl chloride
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

phenols (CHEBI:4601 )
benzoate ester (CHEBI:4601 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015684)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	171.726	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000848

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.038 g/L	ALOGPS
logP	3.33	ALOGPS
logP	3.08	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.09	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	59.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	78.21 m³·mol⁻¹	ChemAxon
Polarizability	30.28 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]+	172.362	30932474
DeepCCS	[M-H]-	170.004	30932474
DeepCCS	[M-2H]-	203.012	30932474
DeepCCS	[M+Na]+	178.455	30932474
AllCCS	[M+H]+	169.5	32859911
AllCCS	[M+H-H2O]+	166.3	32859911
AllCCS	[M+NH4]+	172.5	32859911
AllCCS	[M+Na]+	173.3	32859911
AllCCS	[M-H]-	168.1	32859911
AllCCS	[M+Na-2H]-	167.8	32859911
AllCCS	[M+HCOO]-	167.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diloxanide	CN(C(=O)C(Cl)Cl)C1=CC=C(OC(=O)C2=CC=CO2)C=C1	3545.7	Standard polar	33892256
Diloxanide	CN(C(=O)C(Cl)Cl)C1=CC=C(OC(=O)C2=CC=CO2)C=C1	2756.8	Standard non polar	33892256
Diloxanide	CN(C(=O)C(Cl)Cl)C1=CC=C(OC(=O)C2=CC=CO2)C=C1	2338.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Diloxanide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9210000000-155781bb2d496f2f73d6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diloxanide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diloxanide 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 - Diloxanide , positive-QTOF	splash10-0002-9321100000-2db11dd84428f82ca90e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 10V, Positive-QTOF	splash10-004i-0329000000-1262050a3c668ecb16dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 20V, Positive-QTOF	splash10-00or-0759000000-713dc68946d3510d857a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 40V, Positive-QTOF	splash10-0229-0900000000-e8be416029e730eec9b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 10V, Negative-QTOF	splash10-004i-0019000000-cebc6857c99a38b12002	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 20V, Negative-QTOF	splash10-00or-0479000000-1fd0103d81f6101d6ccf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 40V, Negative-QTOF	splash10-00dl-4910000000-8e2db9b32afa86e51d0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 10V, Positive-QTOF	splash10-004i-0009000000-b367b5d264a721a31829	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 20V, Positive-QTOF	splash10-004i-1029000000-970964c4b48692161e11	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 40V, Positive-QTOF	splash10-006t-6921000000-06fe5bc95cea9426f994	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 10V, Negative-QTOF	splash10-004i-0009000000-341d0e7a1b163c73a23a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 20V, Negative-QTOF	splash10-01ea-5496000000-ab18fdf2aed6acb29d76	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diloxanide 40V, Negative-QTOF	splash10-00e9-5930000000-9c89cb45f3d811d650fc	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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 DB08792	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08792	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DBSALT001813

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

18400

KEGG Compound ID

C07637

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diloxanide

METLIN ID

Not Available

PubChem Compound

19529

PDB ID

Not Available

ChEBI ID

4601

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

McAuley JB, Herwaldt BL, Stokes SL, Becher JA, Roberts JM, Michelson MK, Juranek DD: Diloxanide furoate for treating asymptomatic Entamoeba histolytica cyst passers: 14 years' experience in the United States. Clin Infect Dis. 1992 Sep;15(3):464-8. [PubMed:1520794 ]

Showing metabocard for Diloxanide (HMDB0015684)

MOL for HMDB0015684 (Diloxanide)

3D MOL for HMDB0015684 (Diloxanide)

3D SDF for HMDB0015684 (Diloxanide)

3D-SDF for HMDB0015684 (Diloxanide)

PDB for HMDB0015684 (Diloxanide)

3D PDB for HMDB0015684 (Diloxanide)

SMILES for HMDB0015684 (Diloxanide)

INCHI for HMDB0015684 (Diloxanide)

Structure for HMDB0015684 (Diloxanide)

3D Structure for HMDB0015684 (Diloxanide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra