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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 19:25:17 UTC

Update Date

2021-09-26 23:14:56 UTC

HMDB ID

HMDB0258188

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide

Description

N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide, also known as 3',5'-dichloro-2,4'-dihydroxybenzanilide or N-salicylo-(2,6-dichloro-4-aminophenol), 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. Based on a literature review a small amount of articles have been published on N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-(3,5-dichloro-4-hydroxyphenyl)-2-hydroxybenzamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0258188
     RDKit          3D
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide
 28 29  0  0  0  0  0  0  0  0999 V2000
   -0.0798    1.5951   -1.0856 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4411    0.7126   -0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287   -0.2853    0.2686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209   -0.4601    0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798    0.2067   -0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8553    0.0172   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419    0.8778   -1.9700 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4622   -0.8402    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8338   -1.0662    0.1029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132   -1.5177    1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4583   -2.6290    2.1831 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3536   -1.3401    1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125    0.7801   -0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6147    1.8952   -0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9763    2.0196   -0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6455    0.9382    0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9776   -0.1995    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6630   -1.2633    1.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5904   -0.2798    0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1961   -0.9977    0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744    0.8788   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4849   -0.6395   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7200   -1.8478    1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387    2.7170   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750    2.9317   -0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086    0.9954    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0278   -2.0036    0.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -1.1955    0.6641 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  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 12  4  1  0
 19 13  1  0
  3 20  1  0
  5 21  1  0
  9 22  1  0
 12 23  1  0
 14 24  1  0
 15 25  1  0
 16 26  1  0
 18 27  1  0
 19 28  1  0
M  END


  Mrv1652309112121252D          

 19 20  0  0  0  0            999 V2000
    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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    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
   -2.1434   -6.1875    0.0000 C   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
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 13 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258188

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=CC(=C1)C(=O)NC1=CC(Cl)=C(O)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H9Cl2NO3/c14-10-5-8(6-11(15)12(10)18)16-13(19)7-2-1-3-9(17)4-7/h1-6,17-18H,(H,16,19)

> <INCHI_KEY>
ZYIZNUYMGIICGZ-UHFFFAOYSA-N

> <FORMULA>
C13H9Cl2NO3

> <MOLECULAR_WEIGHT>
298.12

> <EXACT_MASS>
296.9959486

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
28.113816414076542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(3,5-dichloro-4-hydroxyphenyl)-3-hydroxybenzamide

> <ALOGPS_LOGP>
4.55

> <JCHEM_LOGP>
3.6660893309999993

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.769976512455038

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.448163751990665

> <JCHEM_PKA_STRONGEST_BASIC>
-3.969759307371406

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
75.1629

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(3,5-dichloro-4-hydroxyphenyl)-3-hydroxybenzamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258188
     RDKit          3D
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide
 28 29  0  0  0  0  0  0  0  0999 V2000
   -0.0798    1.5951   -1.0856 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4411    0.7126   -0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287   -0.2853    0.2686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209   -0.4601    0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798    0.2067   -0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8553    0.0172   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419    0.8778   -1.9700 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4622   -0.8402    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8338   -1.0662    0.1029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132   -1.5177    1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4583   -2.6290    2.1831 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3536   -1.3401    1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125    0.7801   -0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6147    1.8952   -0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9763    2.0196   -0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6455    0.9382    0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9776   -0.1995    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6630   -1.2633    1.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5904   -0.2798    0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1961   -0.9977    0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744    0.8788   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4849   -0.6395   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7200   -1.8478    1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387    2.7170   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750    2.9317   -0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086    0.9954    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0278   -2.0036    0.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -1.1955    0.6641 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  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 12  4  1  0
 19 13  1  0
  3 20  1  0
  5 21  1  0
  9 22  1  0
 12 23  1  0
 14 24  1  0
 15 25  1  0
 16 26  1  0
 18 27  1  0
 19 28  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       0.000  -9.240   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      -5.335  -9.240   0.000  0.00  0.00          Cl+0
HETATM   18  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   19 Cl   UNK     0      -2.667 -13.860   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    3    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15                                                            
CONECT   18   14                                                            
CONECT   19   13                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0258188
HETATM    1  O1  UNL     1      -0.080   1.595  -1.086  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.441   0.713  -0.355  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.329  -0.285   0.269  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.721  -0.460   0.182  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.480   0.207  -0.739  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.855   0.017  -0.781  1.00  0.00           C  
HETATM    7 CL1  UNL     1      -4.842   0.878  -1.970  1.00  0.00          CL  
HETATM    8  C5  UNL     1      -4.462  -0.840   0.101  1.00  0.00           C  
HETATM    9  O2  UNL     1      -5.834  -1.066   0.103  1.00  0.00           O  
HETATM   10  C6  UNL     1      -3.713  -1.518   1.032  1.00  0.00           C  
HETATM   11 CL2  UNL     1      -4.458  -2.629   2.183  1.00  0.00          CL  
HETATM   12  C7  UNL     1      -2.354  -1.340   1.085  1.00  0.00           C  
HETATM   13  C8  UNL     1       1.913   0.780  -0.185  1.00  0.00           C  
HETATM   14  C9  UNL     1       2.615   1.895  -0.560  1.00  0.00           C  
HETATM   15  C10 UNL     1       3.976   2.020  -0.435  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.646   0.938   0.103  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.978  -0.199   0.491  1.00  0.00           C  
HETATM   18  O3  UNL     1       4.663  -1.263   1.024  1.00  0.00           O  
HETATM   19  C13 UNL     1       2.590  -0.280   0.345  1.00  0.00           C  
HETATM   20  H1  UNL     1       0.196  -0.998   0.882  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.074   0.879  -1.458  1.00  0.00           H  
HETATM   22  H3  UNL     1      -6.485  -0.640  -0.518  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.720  -1.848   1.798  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.039   2.717  -0.978  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.475   2.932  -0.752  1.00  0.00           H  
HETATM   26  H7  UNL     1       5.709   0.995   0.216  1.00  0.00           H  
HETATM   27  H8  UNL     1       5.028  -2.004   0.422  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.139  -1.196   0.664  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4   20
CONECT    4    5    5   12
CONECT    5    6   21
CONECT    6    7    8    8
CONECT    8    9   10
CONECT    9   22
CONECT   10   11   12   12
CONECT   12   23
CONECT   13   14   14   19
CONECT   14   15   24
CONECT   15   16   16   25
CONECT   16   17   26
CONECT   17   18   19   19
CONECT   18   27
CONECT   19   28
END

HMDB0258188
     RDKit          3D
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide
 28 29  0  0  0  0  0  0  0  0999 V2000
   -0.0798    1.5951   -1.0856 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4411    0.7126   -0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287   -0.2853    0.2686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209   -0.4601    0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798    0.2067   -0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8553    0.0172   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419    0.8778   -1.9700 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4622   -0.8402    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8338   -1.0662    0.1029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132   -1.5177    1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4583   -2.6290    2.1831 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3536   -1.3401    1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125    0.7801   -0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6147    1.8952   -0.5599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9763    2.0196   -0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6455    0.9382    0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9776   -0.1995    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6630   -1.2633    1.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5904   -0.2798    0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1961   -0.9977    0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0744    0.8788   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4849   -0.6395   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7200   -1.8478    1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387    2.7170   -0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750    2.9317   -0.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086    0.9954    0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0278   -2.0036    0.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -1.1955    0.6641 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  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 12  4  1  0
 19 13  1  0
  3 20  1  0
  5 21  1  0
  9 22  1  0
 12 23  1  0
 14 24  1  0
 15 25  1  0
 16 26  1  0
 18 27  1  0
 19 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(3,5-Dichloro-4-hydroxyphenyl)-3-hydroxybenzene-1-carboximidate	HMDB
3',5'-Dichloro-2,4'-dihydroxybenzanilide	HMDB
N-Salicylo-(2,6-dichloro-4-aminophenol)	HMDB

Chemical Formula

C₁₃H₉Cl₂NO₃

Average Molecular Weight

298.12

Monoisotopic Molecular Weight

296.9959486

IUPAC Name

N-(3,5-dichloro-4-hydroxyphenyl)-3-hydroxybenzamide

Traditional Name

N-(3,5-dichloro-4-hydroxyphenyl)-3-hydroxybenzamide

CAS Registry Number

Not Available

SMILES

OC1=CC=CC(=C1)C(=O)NC1=CC(Cl)=C(O)C(Cl)=C1

InChI Identifier

InChI=1S/C13H9Cl2NO3/c14-10-5-8(6-11(15)12(10)18)16-13(19)7-2-1-3-9(17)4-7/h1-6,17-18H,(H,16,19)

InChI Key

ZYIZNUYMGIICGZ-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
Benzoic acid or derivatives
Benzamide
2-chlorophenol
2-halophenol
1,3-dichlorobenzene
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Halobenzene
Chlorobenzene
Aryl halide
Aryl chloride
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.55	ALOGPS
logP	3.67	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	6.45	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.16 m³·mol⁻¹	ChemAxon
Polarizability	28.11 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]+	166.92	30932474
DeepCCS	[M-H]-	164.562	30932474
DeepCCS	[M-2H]-	197.448	30932474
DeepCCS	[M+Na]+	173.013	30932474
AllCCS	[M+H]+	160.7	32859911
AllCCS	[M+H-H2O]+	157.1	32859911
AllCCS	[M+NH4]+	164.0	32859911
AllCCS	[M+Na]+	164.9	32859911
AllCCS	[M-H]-	154.9	32859911
AllCCS	[M+Na-2H]-	154.2	32859911
AllCCS	[M+HCOO]-	153.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.25 minutes	32390414
Predicted by Siyang on May 30, 2022	14.732 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.19 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2273.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	430.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	269.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	334.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	675.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	687.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	153.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1274.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	475.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1555.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	476.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	427.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	519.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	233.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	138.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide	OC1=CC=CC(=C1)C(=O)NC1=CC(Cl)=C(O)C(Cl)=C1	4477.9	Standard polar	33892256
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide	OC1=CC=CC(=C1)C(=O)NC1=CC(Cl)=C(O)C(Cl)=C1	2813.1	Standard non polar	33892256
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide	OC1=CC=CC(=C1)C(=O)NC1=CC(Cl)=C(O)C(Cl)=C1	2821.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C(=O)N(C2=CC(Cl)=C(O[Si](C)(C)C)C(Cl)=C2)[Si](C)(C)C)=C1	2645.3	Semi standard non polar	33892256
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C(=O)N(C2=CC(Cl)=C(O[Si](C)(C)C)C(Cl)=C2)[Si](C)(C)C)=C1	2579.6	Standard non polar	33892256
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C(=O)N(C2=CC(Cl)=C(O[Si](C)(C)C)C(Cl)=C2)[Si](C)(C)C)=C1	2706.0	Standard polar	33892256
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)N(C2=CC(Cl)=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C2)[Si](C)(C)C(C)(C)C)=C1	3440.3	Semi standard non polar	33892256
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)N(C2=CC(Cl)=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C2)[Si](C)(C)C(C)(C)C)=C1	3186.5	Standard non polar	33892256
N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(=O)N(C2=CC(Cl)=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C2)[Si](C)(C)C(C)(C)C)=C1	3009.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-7920000000-159eada60b5a92a58031	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

110672

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124217

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide (HMDB0258188)

MOL for HMDB0258188 (N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide)

3D MOL for HMDB0258188 (N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide)

3D SDF for HMDB0258188 (N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide)

3D-SDF for HMDB0258188 (N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide)

PDB for HMDB0258188 (N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide)

3D PDB for HMDB0258188 (N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide)

SMILES for HMDB0258188 (N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide)

INCHI for HMDB0258188 (N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide)

Structure for HMDB0258188 (N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide)

3D Structure for HMDB0258188 (N-(3,5-Dichloro-4-hydroxyphenyl)-2-hydroxybenzamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra