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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-04-09 21:19:23 UTC

Update Date

2019-07-23 07:13:24 UTC

HMDB ID

HMDB0060008

Secondary Accession Numbers

HMDB60008

Metabolite Identification

Common Name

N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid

Description

N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid, also known as N-3-CL-2-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-hydroxymethyl-3-chlorophenyl)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

HMDB0060008
     RDKit          3D
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6519    0.2473   -2.6884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5440    0.2493   -2.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4038    0.7155   -2.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5638   -0.2595   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7960   -0.6203   -0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9045   -1.0466    1.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802   -1.1147    1.9379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458   -0.7596    1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.3328    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1574   -0.0875   -0.3936 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9909    0.3285    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9820    0.9533    1.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1673    1.4120    2.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3804    1.2434    1.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4059    0.6196    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9448    0.3996   -0.5723 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2392    0.1772   -0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2876   -0.4854   -1.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6045   -0.5436   -2.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0940    1.6755   -2.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6920   -0.5694   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8952   -1.3271    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8832   -1.4584    2.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6775   -0.8728    2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -0.2738   -1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0650    1.1645    2.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416    1.9045    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2797    1.6064    1.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -1.5196   -1.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7155    0.0472   -2.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9799   -1.4726   -2.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
  9  4  1  0
 17 11  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 18 29  1  0
 18 30  1  0
 19 31  1  0
M  END


  Mrv0541 04091314192D          

 19 20  0  0  0  0            999 V2000
    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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
  5  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
 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
 13 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060008

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=C(NC2=CC=CC=C2C(O)=O)C=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C14H12ClNO3/c15-11-5-3-7-13(10(11)8-17)16-12-6-2-1-4-9(12)14(18)19/h1-7,16-17H,8H2,(H,18,19)

> <INCHI_KEY>
BMLZYLYIEWXTCM-UHFFFAOYSA-N

> <FORMULA>
C14H12ClNO3

> <MOLECULAR_WEIGHT>
277.703

> <EXACT_MASS>
277.050570962

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.20712664605991

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[3-chloro-2-(hydroxymethyl)phenyl]amino}benzoic acid

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
4.207449408333333

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.656036031410352

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8596356917149675

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9500696328137117

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
73.42110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[3-chloro-2-(hydroxymethyl)phenyl]amino}benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060008
     RDKit          3D
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6519    0.2473   -2.6884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5440    0.2493   -2.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4038    0.7155   -2.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5638   -0.2595   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7960   -0.6203   -0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9045   -1.0466    1.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802   -1.1147    1.9379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458   -0.7596    1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.3328    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1574   -0.0875   -0.3936 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9909    0.3285    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9820    0.9533    1.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1673    1.4120    2.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3804    1.2434    1.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4059    0.6196    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9448    0.3996   -0.5723 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2392    0.1772   -0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2876   -0.4854   -1.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6045   -0.5436   -2.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0940    1.6755   -2.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6920   -0.5694   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8952   -1.3271    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8832   -1.4584    2.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6775   -0.8728    2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -0.2738   -1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0650    1.1645    2.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416    1.9045    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2797    1.6064    1.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -1.5196   -1.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7155    0.0472   -2.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9799   -1.4726   -2.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
  9  4  1  0
 17 11  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 18 29  1  0
 18 30  1  0
 19 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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      12.003  -2.310   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   13                                                            
CONECT   18   12   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0060008
HETATM    1  O1  UNL     1      -3.652   0.247  -2.688  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.544   0.249  -2.054  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.404   0.716  -2.674  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.564  -0.259  -0.660  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.796  -0.620  -0.149  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.904  -1.047   1.147  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.780  -1.115   1.938  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.546  -0.760   1.439  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.452  -0.333   0.136  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.157  -0.087  -0.394  1.00  0.00           N  
HETATM   11  C8  UNL     1       0.991   0.328   0.275  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.982   0.953   1.498  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.167   1.412   2.103  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.380   1.243   1.472  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.406   0.620   0.243  1.00  0.00           C  
HETATM   16 CL1  UNL     1       4.945   0.400  -0.572  1.00  0.00          CL  
HETATM   17  C13 UNL     1       2.239   0.177  -0.333  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.288  -0.485  -1.639  1.00  0.00           C  
HETATM   19  O3  UNL     1       3.604  -0.544  -2.082  1.00  0.00           O  
HETATM   20  H1  UNL     1      -1.094   1.676  -2.478  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.692  -0.569  -0.771  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.895  -1.327   1.531  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.883  -1.458   2.978  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.677  -0.873   2.110  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.037  -0.274  -1.436  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.065   1.165   2.050  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.142   1.905   3.074  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.280   1.606   1.960  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.894  -1.520  -1.586  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.715   0.047  -2.427  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.980  -1.473  -2.011  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5    5    9
CONECT    5    6   21
CONECT    6    7    7   22
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10
CONECT   10   11   25
CONECT   11   12   12   17
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   14   15   28
CONECT   15   16   17   17
CONECT   17   18
CONECT   18   19   29   30
CONECT   19   31
END

HMDB0060008
     RDKit          3D
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6519    0.2473   -2.6884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5440    0.2493   -2.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4038    0.7155   -2.6738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5638   -0.2595   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7960   -0.6203   -0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9045   -1.0466    1.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802   -1.1147    1.9379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458   -0.7596    1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.3328    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1574   -0.0875   -0.3936 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9909    0.3285    0.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9820    0.9533    1.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1673    1.4120    2.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3804    1.2434    1.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4059    0.6196    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9448    0.3996   -0.5723 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2392    0.1772   -0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2876   -0.4854   -1.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6045   -0.5436   -2.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0940    1.6755   -2.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6920   -0.5694   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8952   -1.3271    1.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8832   -1.4584    2.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6775   -0.8728    2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -0.2738   -1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0650    1.1645    2.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1416    1.9045    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2797    1.6064    1.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -1.5196   -1.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7155    0.0472   -2.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9799   -1.4726   -2.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
  9  4  1  0
 17 11  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 18 29  1  0
 18 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(2-Hydroxymethyl-3-chlorophenyl)anthranilate	Generator
N-3-CL-2-HMPA	HMDB
2-{[3-chloro-2-(hydroxymethyl)phenyl]amino}benzoate	Generator
N-(3-Chloro-2-hydroxymethylphenyl)anthranilic acid	MeSH

Chemical Formula

C₁₄H₁₂ClNO₃

Average Molecular Weight

277.703

Monoisotopic Molecular Weight

277.050570962

IUPAC Name

2-{[3-chloro-2-(hydroxymethyl)phenyl]amino}benzoic acid

Traditional Name

2-{[3-chloro-2-(hydroxymethyl)phenyl]amino}benzoic acid

CAS Registry Number

Not Available

SMILES

OCC1=C(NC2=CC=CC=C2C(O)=O)C=CC=C1Cl

InChI Identifier

InChI=1S/C14H12ClNO3/c15-11-5-3-7-13(10(11)8-17)16-12-6-2-1-4-9(12)14(18)19/h1-7,16-17H,8H2,(H,18,19)

InChI Key

BMLZYLYIEWXTCM-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
Benzoyl
Benzyl alcohol
Aniline or substituted anilines
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Vinylogous amide
Amino acid or derivatives
Amino acid
Secondary amine
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Primary alcohol
Aromatic alcohol
Alcohol
Organohalogen compound
Organochloride
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060008)

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	0.04 g/L	ALOGPS
logP	3.54	ALOGPS
logP	4.21	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	-3	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	4	ChemAxon
Refractivity	73.42 m³·mol⁻¹	ChemAxon
Polarizability	27.21 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]+	154.146	30932474
DeepCCS	[M-H]-	151.751	30932474
DeepCCS	[M-2H]-	184.716	30932474
DeepCCS	[M+Na]+	160.2	30932474
AllCCS	[M+H]+	159.9	32859911
AllCCS	[M+H-H2O]+	156.3	32859911
AllCCS	[M+NH4]+	163.2	32859911
AllCCS	[M+Na]+	164.2	32859911
AllCCS	[M-H]-	158.5	32859911
AllCCS	[M+Na-2H]-	158.0	32859911
AllCCS	[M+HCOO]-	157.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid	OCC1=C(NC2=CC=CC=C2C(O)=O)C=CC=C1Cl	4024.0	Standard polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid	OCC1=C(NC2=CC=CC=C2C(O)=O)C=CC=C1Cl	2453.2	Standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid	OCC1=C(NC2=CC=CC=C2C(O)=O)C=CC=C1Cl	2498.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,1TMS,isomer #1	C[Si](C)(C)OCC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(=O)O	2450.8	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=CC=C1NC1=CC=CC(Cl)=C1CO	2380.4	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,1TMS,isomer #3	C[Si](C)(C)N(C1=CC=CC=C1C(=O)O)C1=CC=CC(Cl)=C1CO	2345.5	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,2TMS,isomer #1	C[Si](C)(C)OCC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(=O)O[Si](C)(C)C	2447.8	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,2TMS,isomer #2	C[Si](C)(C)OCC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C	2386.5	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C1=CC=CC(Cl)=C1CO)[Si](C)(C)C	2330.2	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,3TMS,isomer #1	C[Si](C)(C)OCC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O[Si](C)(C)C)[Si](C)(C)C	2411.4	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,3TMS,isomer #1	C[Si](C)(C)OCC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O[Si](C)(C)C)[Si](C)(C)C	2434.5	Standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,3TMS,isomer #1	C[Si](C)(C)OCC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O[Si](C)(C)C)[Si](C)(C)C	2697.7	Standard polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(=O)O	2688.7	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC1=CC=CC(Cl)=C1CO	2635.0	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)O)C1=CC=CC(Cl)=C1CO	2574.5	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2899.1	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C(C)(C)C	2829.9	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C1=CC=CC(Cl)=C1CO)[Si](C)(C)C(C)(C)C	2789.3	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3038.1	Semi standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2980.5	Standard non polar	33892256
N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3000.7	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-hydroxymethyl-3-chlorophenyl)anthranilic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-08gi-0290000000-cc588905ec5192faa1a8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid GC-MS (2 TMS) - 70eV, Positive	splash10-05ai-7229400000-fa228ab68ec839dc7ae6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)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-hydroxymethyl-3-chlorophenyl)anthranilic acid 10V, Positive-QTOF	splash10-03fr-0090000000-acd1f2578ce43700c276	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid 20V, Positive-QTOF	splash10-03dl-0190000000-c2d9cc0580041a0da09d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid 40V, Positive-QTOF	splash10-03dl-2590000000-eb176434c756196392ed	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid 10V, Negative-QTOF	splash10-0059-0090000000-9506db197eee11f0fce6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid 20V, Negative-QTOF	splash10-0udi-0090000000-77589c2d901fecc93c1a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid 40V, Negative-QTOF	splash10-0udi-2390000000-a2327fcf6cbc42222769	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid 10V, Positive-QTOF	splash10-03fu-0190000000-7f06686a22076fbb66db	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid 20V, Positive-QTOF	splash10-03dl-0090000000-3899d1d7ba9128a986c2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid 40V, Positive-QTOF	splash10-02fx-0290000000-c3605ccc102f17faf9af	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid 10V, Negative-QTOF	splash10-003r-1090000000-19f71420793653b10db5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid 20V, Negative-QTOF	splash10-001i-9010000000-8b0fb0a222c7abe9a750	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid 40V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	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

53703

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-hydroxymethyl-3-chlorophenyl)anthranilic acid (HMDB0060008)

MOL for HMDB0060008 (N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid)

3D MOL for HMDB0060008 (N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid)

3D SDF for HMDB0060008 (N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid)

3D-SDF for HMDB0060008 (N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid)

PDB for HMDB0060008 (N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid)

3D PDB for HMDB0060008 (N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid)

SMILES for HMDB0060008 (N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid)

INCHI for HMDB0060008 (N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid)

Structure for HMDB0060008 (N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid)

3D Structure for HMDB0060008 (N-(2-hydroxymethyl-3-chlorophenyl)anthranilic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra