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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-04-09 21:19:27 UTC

Update Date

2019-07-23 07:13:24 UTC

HMDB ID

HMDB0060009

Secondary Accession Numbers

HMDB60009

Metabolite Identification

Common Name

N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid

Description

N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid, also known as N-3-CL-4-hmpa, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060009
     RDKit          3D
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid
 31 32  0  0  0  0  0  0  0  0999 V2000
    1.9418   -2.2968   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186   -0.8530   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -0.0198    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842   -0.5899    0.0103 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253    0.0155   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6196    1.2045   -0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8450    1.8068   -1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0123    1.2348   -0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9380    0.0789   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7052   -0.5393    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536   -1.7233    1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8697   -2.2118    1.4416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -2.4040    1.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181    1.3051    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290    1.7458    0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294    0.9388    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9259    1.4298    0.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4148   -0.3912   -0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924   -1.4387   -0.3279 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -2.4028   -1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8554   -2.6843   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278   -2.8908    0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693   -1.6566    0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.6203   -1.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8673    2.7391   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9680    1.7261   -0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8606   -0.3643    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153   -2.1843    2.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237    2.0335    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7103    2.7845    0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7057    0.8180    0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18  2  1  0
 10  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
M  END

  Mrv0541 04091314192D          

 19 20  0  0  0  0            999 V2000
    1.5321   -0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8177   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8177   -1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5321   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5321    0.1179    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9611   -0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9611   -2.3571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9611   -3.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -3.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -4.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9611   -4.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756   -4.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756   -3.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900   -3.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900   -2.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1045   -3.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1032   -0.7071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  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  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060009

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(Cl)C(O)=CC=C1NC1=C(C=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H12ClNO3/c1-8-10(6-7-12(17)13(8)15)16-11-5-3-2-4-9(11)14(18)19/h2-7,16-17H,1H3,(H,18,19)

> <INCHI_KEY>
VRNDVGVAHVCCCU-UHFFFAOYSA-N

> <FORMULA>
C14H12ClNO3

> <MOLECULAR_WEIGHT>
277.703

> <EXACT_MASS>
277.050570962

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.560244079530094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3-chloro-4-hydroxy-2-methylphenyl)amino]benzoic acid

> <ALOGPS_LOGP>
4.01

> <JCHEM_LOGP>
5.184655243333333

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.545091013075034

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.893117557961205

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6302730996263374

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
73.6273

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3-chloro-4-hydroxy-2-methylphenyl)amino]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060009
     RDKit          3D
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid
 31 32  0  0  0  0  0  0  0  0999 V2000
    1.9418   -2.2968   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186   -0.8530   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -0.0198    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842   -0.5899    0.0103 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253    0.0155   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6196    1.2045   -0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8450    1.8068   -1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0123    1.2348   -0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9380    0.0789   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7052   -0.5393    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536   -1.7233    1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8697   -2.2118    1.4416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -2.4040    1.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181    1.3051    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290    1.7458    0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294    0.9388    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9259    1.4298    0.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4148   -0.3912   -0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924   -1.4387   -0.3279 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -2.4028   -1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8554   -2.6843   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278   -2.8908    0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693   -1.6566    0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.6203   -1.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8673    2.7391   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9680    1.7261   -0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8606   -0.3643    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153   -2.1843    2.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237    2.0335    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7103    2.7845    0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7057    0.8180    0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18  2  1  0
 10  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 09-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-APR-13         0                                  
HETATM    1  C   UNK     0       2.860  -1.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.526  -2.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.526  -3.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.860  -4.400   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.194  -3.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.194  -2.090   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       2.860   0.220   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0       5.527  -1.320   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.527  -4.400   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.527  -5.940   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.194  -6.710   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.194  -8.250   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.527  -9.020   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.861  -8.250   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.861  -6.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.195  -5.940   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.195  -4.400   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.528  -6.710   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.193  -1.320   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    1    8                                                  
CONECT    7    1                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0060009
HETATM    1  C1  UNL     1       1.942  -2.297  -0.466  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.119  -0.853  -0.154  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.007  -0.020   0.046  1.00  0.00           C  
HETATM    4  N1  UNL     1      -0.284  -0.590   0.010  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.525   0.016  -0.148  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.620   1.204  -0.879  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.845   1.807  -1.166  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.012   1.235  -0.730  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.938   0.079  -0.019  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.705  -0.539   0.279  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.754  -1.723   1.077  1.00  0.00           C  
HETATM   12  O1  UNL     1      -3.870  -2.212   1.442  1.00  0.00           O  
HETATM   13  O2  UNL     1      -1.649  -2.404   1.503  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.218   1.305   0.332  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.529   1.746   0.404  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.629   0.939   0.209  1.00  0.00           C  
HETATM   17  O3  UNL     1       4.926   1.430   0.292  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.415  -0.391  -0.076  1.00  0.00           C  
HETATM   19 CL1  UNL     1       4.792  -1.439  -0.328  1.00  0.00          CL  
HETATM   20  H1  UNL     1       1.097  -2.403  -1.210  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.855  -2.684  -0.931  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.628  -2.891   0.410  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.269  -1.657   0.097  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.714   1.620  -1.248  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.867   2.739  -1.741  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.968   1.726  -0.968  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.861  -0.364   0.319  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.115  -2.184   2.328  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.424   2.033   0.543  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.710   2.785   0.627  1.00  0.00           H  
HETATM   31  H12 UNL     1       5.706   0.818   0.145  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   18
CONECT    3    4   14
CONECT    4    5   23
CONECT    5    6    6   10
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   26
CONECT    9   10   10   27
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   28
CONECT   14   15   15   29
CONECT   15   16   30
CONECT   16   17   18   18
CONECT   17   31
CONECT   18   19
END

HMDB0060009
     RDKit          3D
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid
 31 32  0  0  0  0  0  0  0  0999 V2000
    1.9418   -2.2968   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186   -0.8530   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -0.0198    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842   -0.5899    0.0103 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253    0.0155   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6196    1.2045   -0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8450    1.8068   -1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0123    1.2348   -0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9380    0.0789   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7052   -0.5393    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536   -1.7233    1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8697   -2.2118    1.4416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -2.4040    1.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181    1.3051    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290    1.7458    0.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294    0.9388    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9259    1.4298    0.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4148   -0.3912   -0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924   -1.4387   -0.3279 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0971   -2.4028   -1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8554   -2.6843   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6278   -2.8908    0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693   -1.6566    0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.6203   -1.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8673    2.7391   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9680    1.7261   -0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8606   -0.3643    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1153   -2.1843    2.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237    2.0335    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7103    2.7845    0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7057    0.8180    0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18  2  1  0
 10  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(2-Methyl-3-chloro-4-hydroxyphenyl)anthranilate	Generator
N-3-CL-4-HMPA	HMDB
2-[(3-Chloro-4-hydroxy-2-methylphenyl)amino]benzoate	Generator
N-(3-Chloro-4-hydroxy-2-methylphenyl)anthranilic acid	MeSH

Chemical Formula

C₁₄H₁₂ClNO₃

Average Molecular Weight

277.703

Monoisotopic Molecular Weight

277.050570962

IUPAC Name

2-[(3-chloro-4-hydroxy-2-methylphenyl)amino]benzoic acid

Traditional Name

2-[(3-chloro-4-hydroxy-2-methylphenyl)amino]benzoic acid

CAS Registry Number

Not Available

SMILES

CC1=C(Cl)C(O)=CC=C1NC1=C(C=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C14H12ClNO3/c1-8-10(6-7-12(17)13(8)15)16-11-5-3-2-4-9(11)14(18)19/h2-7,16-17H,1H3,(H,18,19)

InChI Key

VRNDVGVAHVCCCU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzoic acids

Alternative Parents

Substituents

Aminobenzoic acid
Benzoic acid
Aminophenol
P-aminophenol
Benzoyl
2-halophenol
M-cresol
2-chlorophenol
Aniline or substituted anilines
Aminotoluene
Toluene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Chlorobenzene
Halobenzene
Aryl halide
Aryl chloride
Vinylogous amide
Amino acid
Amino acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Secondary amine
Monocarboxylic acid or derivatives
Amine
Organochloride
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060009)

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
Water Solubility	0.035 g/L	ALOGPS
logP	4.01	ALOGPS
logP	5.18	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	-0.63	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.63 m³·mol⁻¹	ChemAxon
Polarizability	27.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	158.639	30932474
DeepCCS	[M-H]-	156.281	30932474
DeepCCS	[M-2H]-	189.167	30932474
DeepCCS	[M+Na]+	164.732	30932474
AllCCS	[M+H]+	159.5	32859911
AllCCS	[M+H-H2O]+	155.9	32859911
AllCCS	[M+NH4]+	162.9	32859911
AllCCS	[M+Na]+	163.9	32859911
AllCCS	[M-H]-	158.2	32859911
AllCCS	[M+Na-2H]-	157.6	32859911
AllCCS	[M+HCOO]-	157.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid	CC1=C(Cl)C(O)=CC=C1NC1=C(C=CC=C1)C(O)=O	4167.7	Standard polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid	CC1=C(Cl)C(O)=CC=C1NC1=C(C=CC=C1)C(O)=O	2516.4	Standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid	CC1=C(Cl)C(O)=CC=C1NC1=C(C=CC=C1)C(O)=O	2477.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,1TMS,isomer #1	CC1=C(NC2=CC=CC=C2C(=O)O)C=CC(O[Si](C)(C)C)=C1Cl	2489.6	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,1TMS,isomer #2	CC1=C(NC2=CC=CC=C2C(=O)O[Si](C)(C)C)C=CC(O)=C1Cl	2446.7	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,1TMS,isomer #3	CC1=C(N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)C=CC(O)=C1Cl	2426.0	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,2TMS,isomer #1	CC1=C(NC2=CC=CC=C2C(=O)O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C1Cl	2481.7	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,2TMS,isomer #2	CC1=C(N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C1Cl	2400.1	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,2TMS,isomer #3	CC1=C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)C=CC(O)=C1Cl	2387.6	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,3TMS,isomer #1	CC1=C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C1Cl	2416.6	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,3TMS,isomer #1	CC1=C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C1Cl	2475.5	Standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,3TMS,isomer #1	CC1=C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C1Cl	2617.7	Standard polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,1TBDMS,isomer #1	CC1=C(NC2=CC=CC=C2C(=O)O)C=CC(O[Si](C)(C)C(C)(C)C)=C1Cl	2765.0	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,1TBDMS,isomer #2	CC1=C(NC2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)C=CC(O)=C1Cl	2701.3	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,1TBDMS,isomer #3	CC1=C(N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)C=CC(O)=C1Cl	2667.8	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,2TBDMS,isomer #1	CC1=C(NC2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C1Cl	2958.6	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,2TBDMS,isomer #2	CC1=C(N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C1Cl	2902.6	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,2TBDMS,isomer #3	CC1=C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC(O)=C1Cl	2853.8	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,3TBDMS,isomer #1	CC1=C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C1Cl	3098.6	Semi standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,3TBDMS,isomer #1	CC1=C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C1Cl	3030.9	Standard non polar	33892256
N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid,3TBDMS,isomer #1	CC1=C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C1Cl	2955.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-06ur-0190000000-3211de4a2dbc31b845c0	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-9007500000-8fd41c1e4bf8ad21b46a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 10V, Positive-QTOF	splash10-01t9-0090000000-5d393a4f316a2c3fb387	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 20V, Positive-QTOF	splash10-01qc-0290000000-59f80e9d9b8c38fc3d42	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 40V, Positive-QTOF	splash10-0gwf-3980000000-b0e30bd4eaef0dcd4030	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 10V, Negative-QTOF	splash10-003r-0090000000-d9da8c8c36b29e840a37	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 20V, Negative-QTOF	splash10-001i-0090000000-2be334637395377315e1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 40V, Negative-QTOF	splash10-000t-1790000000-84c621abf898995511dc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 10V, Positive-QTOF	splash10-03fr-0090000000-d7dd00b9727345a96c84	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 20V, Positive-QTOF	splash10-03di-0090000000-136bc2d3572b6cc89047	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 40V, Positive-QTOF	splash10-001i-0590000000-054183cbf87ab4c80435	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 10V, Negative-QTOF	splash10-0059-0090000000-0f94f63873bedf4f5770	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 20V, Negative-QTOF	splash10-001i-1090000000-3b5744e9bc153a26c09c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid 40V, Negative-QTOF	splash10-001i-3690000000-2eeec1883b2dbfa2ba7d	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53704

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

Not Available

Showing metabocard for N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid (HMDB0060009)

MOL for HMDB0060009 (N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid)

3D MOL for HMDB0060009 (N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid)

3D SDF for HMDB0060009 (N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid)

3D-SDF for HMDB0060009 (N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid)

PDB for HMDB0060009 (N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid)

3D PDB for HMDB0060009 (N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid)

SMILES for HMDB0060009 (N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid)

INCHI for HMDB0060009 (N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid)

Structure for HMDB0060009 (N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid)

3D Structure for HMDB0060009 (N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra