Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:51:30 UTC

Update Date

2021-09-26 22:54:30 UTC

HMDB ID

HMDB0245807

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Amino-4-methoxybenzanilide

Description

3-Amino-4-methoxybenzanilide, also known as amantadine or amanta-sulfate-azu, 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 very few articles have been published on 3-Amino-4-methoxybenzanilide. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-amino-4-methoxybenzanilide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-Amino-4-methoxybenzanilide 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

HMDB0245807
     RDKit          3D
3-Amino-4-methoxybenzanilide
 32 33  0  0  0  0  0  0  0  0999 V2000
    2.1495   -2.4784   -4.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477   -1.8882   -3.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121   -1.3358   -2.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6487   -1.3174   -2.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0461   -0.7533   -1.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6238   -0.1944   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1439    0.3906    0.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5084    0.9623    1.8446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    0.4009    0.7434 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    0.9715    1.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250    1.8358    1.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9671    2.3954    2.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6920    2.1067    3.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6496    1.2390    4.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146    0.6847    3.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -0.2233   -0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7144   -0.7869   -1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286   -0.8086   -1.3963 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488   -3.5312   -4.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8497   -2.4600   -5.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520   -1.9171   -4.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -1.7426   -3.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242   -0.7591   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574    1.9285    1.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4605    2.0777    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7731    3.0666    2.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2725    2.5440    4.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314    1.0101    5.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874   -0.0038    3.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524    0.2064    0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6661   -1.3816   -2.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6449   -0.2385   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 18 31  1  0
 18 32  1  0
M  END


  Mrv1572004251606142D          

 18 19  0  0  0  0            999 V2000
   -4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    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
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 10  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  4  0  0  0
 16 14  2  0  0  0  0
 17 14  1  0  0  0  0
 18  1  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245807

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(N)C=C(C=C1)C(O)=NC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14N2O2/c1-18-13-8-7-10(9-12(13)15)14(17)16-11-5-3-2-4-6-11/h2-9H,15H2,1H3,(H,16,17)

> <INCHI_KEY>
LHMQDVIHBXWNII-UHFFFAOYSA-N

> <FORMULA>
C14H14N2O2

> <MOLECULAR_WEIGHT>
242.278

> <EXACT_MASS>
242.105527699

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.235304548246535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-amino-4-methoxy-N-phenylbenzene-1-carboximidic acid

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.8059900723333326

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.558176450118377

> <JCHEM_PKA_STRONGEST_BASIC>
3.3366287439201336

> <JCHEM_POLAR_SURFACE_AREA>
67.84

> <JCHEM_REFRACTIVITY>
73.51020000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-amino-4-methoxy-N-phenylbenzenecarboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245807
     RDKit          3D
3-Amino-4-methoxybenzanilide
 32 33  0  0  0  0  0  0  0  0999 V2000
    2.1495   -2.4784   -4.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477   -1.8882   -3.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121   -1.3358   -2.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6487   -1.3174   -2.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0461   -0.7533   -1.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6238   -0.1944   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1439    0.3906    0.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5084    0.9623    1.8446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    0.4009    0.7434 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    0.9715    1.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250    1.8358    1.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9671    2.3954    2.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6920    2.1067    3.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6496    1.2390    4.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146    0.6847    3.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -0.2233   -0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7144   -0.7869   -1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286   -0.8086   -1.3963 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488   -3.5312   -4.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8497   -2.4600   -5.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520   -1.9171   -4.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -1.7426   -3.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242   -0.7591   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574    1.9285    1.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4605    2.0777    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7731    3.0666    2.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2725    2.5440    4.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314    1.0101    5.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874   -0.0038    3.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524    0.2064    0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6661   -1.3816   -2.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6449   -0.2385   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 18 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 25-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-16         0                                  
HETATM    1  C   UNK     0      -8.002  13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -9.336  11.550   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -5.335   6.160   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      -8.002   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.668  13.090   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   10                                                       
CONECT    8    7   13                                                       
CONECT    9   10   12                                                       
CONECT   10    7    9   14                                                  
CONECT   11    5    6   16                                                  
CONECT   12    9   13   15                                                  
CONECT   13    8   12   18                                                  
CONECT   14   10   16   17                                                  
CONECT   15   12                                                            
CONECT   16   11   14                                                       
CONECT   17   14                                                            
CONECT   18    1   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0245807
HETATM    1  C1  UNL     1       2.149  -2.478  -4.614  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.748  -1.888  -3.480  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.012  -1.336  -2.455  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.649  -1.317  -2.458  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.046  -0.753  -1.411  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.624  -0.194  -0.335  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.144   0.391   0.752  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.508   0.962   1.845  1.00  0.00           O  
HETATM    9  N1  UNL     1      -1.431   0.401   0.743  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.188   0.971   1.803  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.225   1.836   1.536  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.967   2.395   2.578  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.692   2.107   3.900  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.650   1.239   4.151  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.915   0.685   3.121  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.001  -0.223  -0.351  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.714  -0.787  -1.397  1.00  0.00           C  
HETATM   18  N2  UNL     1       4.129  -0.809  -1.396  1.00  0.00           N  
HETATM   19  H1  UNL     1       1.949  -3.531  -4.397  1.00  0.00           H  
HETATM   20  H2  UNL     1       2.850  -2.460  -5.489  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.252  -1.917  -4.946  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.100  -1.743  -3.278  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.124  -0.759  -1.452  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.857   1.929   1.740  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.461   2.078   0.519  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.773   3.067   2.382  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.273   2.544   4.716  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.431   1.010   5.183  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.087  -0.004   3.312  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.552   0.206   0.478  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.666  -1.382  -2.070  1.00  0.00           H  
HETATM   32  H14 UNL     1       4.645  -0.238  -0.707  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   22
CONECT    5    6    6   23
CONECT    6    7   16
CONECT    7    8    9    9
CONECT    8   24
CONECT    9   10
CONECT   10   11   11   15
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   29
CONECT   16   17   17   30
CONECT   17   18
CONECT   18   31   32
END

HMDB0245807
     RDKit          3D
3-Amino-4-methoxybenzanilide
 32 33  0  0  0  0  0  0  0  0999 V2000
    2.1495   -2.4784   -4.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477   -1.8882   -3.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121   -1.3358   -2.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6487   -1.3174   -2.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0461   -0.7533   -1.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6238   -0.1944   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1439    0.3906    0.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5084    0.9623    1.8446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    0.4009    0.7434 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    0.9715    1.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250    1.8358    1.5357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9671    2.3954    2.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6920    2.1067    3.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6496    1.2390    4.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146    0.6847    3.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -0.2233   -0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7144   -0.7869   -1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286   -0.8086   -1.3963 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488   -3.5312   -4.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8497   -2.4600   -5.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520   -1.9171   -4.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -1.7426   -3.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242   -0.7591   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574    1.9285    1.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4605    2.0777    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7731    3.0666    2.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2725    2.5440    4.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314    1.0101    5.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874   -0.0038    3.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524    0.2064    0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6661   -1.3816   -2.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6449   -0.2385   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 18 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Amanta-sulfate-azu	HMDB
Amantadin stada	HMDB
Amanta	HMDB
Amantadine	HMDB
Viregyt	HMDB
Infecto-flu	HMDB
Hydrochloride, amantadine	HMDB
Infecto flu	HMDB
PMS-Amantadine	HMDB
Cerebramed	HMDB
Amantasulfateazu	HMDB
AZU, amantadin	HMDB
Amantadin-neuraxpharm	HMDB
Mantadix	HMDB
Amantadin azu	HMDB
Amantadin-ratiopharm	HMDB
Amantadina juventus	HMDB
Amantadin ratiopharm	HMDB
Sulfate, amantadine	HMDB
1 Aminoadamantane	HMDB
1-Aminoadamantane	HMDB
Amanta sulfate azu	HMDB
Stada, amantadin	HMDB
Gen amantadine	HMDB
GenAmantadine	HMDB
Llorente, amantadina	HMDB
Symadine	HMDB
PMSAmantadine	HMDB
Amantadine hydrochloride	HMDB
PMS Amantadine	HMDB
Amanta-hci-azu	HMDB
Adekin	HMDB
Amixx	HMDB
Gen-amantadine	HMDB
Adamantylamine	HMDB
AmantaHCIAZU	HMDB
Amantadina llorente	HMDB
Endantadine	HMDB
AL, amantadin	HMDB
Infex	HMDB
Tregor	HMDB
Symmetrel	HMDB
Amantadin neuraxpharm	HMDB
Amantadine sulfate	HMDB
Midantan	HMDB
Amanta hci azu	HMDB
Amantadinneuraxpharm	HMDB
Aman	HMDB
Wiregyt	HMDB
InfectoFlu	HMDB
Juventus, amantadina	HMDB
Amantadin al	HMDB
Amantadinratiopharm	HMDB

Chemical Formula

C₁₄H₁₄N₂O₂

Average Molecular Weight

242.278

Monoisotopic Molecular Weight

242.105527699

IUPAC Name

3-amino-4-methoxy-N-phenylbenzene-1-carboximidic acid

Traditional Name

3-amino-4-methoxy-N-phenylbenzenecarboximidic acid

CAS Registry Number

Not Available

SMILES

COC1=C(N)C=C(C=C1)C(O)=NC1=CC=CC=C1

InChI Identifier

InChI=1S/C14H14N2O2/c1-18-13-8-7-10(9-12(13)15)14(17)16-11-5-3-2-4-6-11/h2-9H,15H2,1H3,(H,16,17)

InChI Key

LHMQDVIHBXWNII-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
Aminobenzoic acid or derivatives
Benzamide
Aminophenyl ether
Benzoic acid or derivatives
Methoxyaniline
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Aniline or substituted anilines
Methoxybenzene
Alkyl aryl ether
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Ether
Carboxylic acid derivative
Primary amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
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)

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	2.25	ALOGPS
logP	2.81	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.56	ChemAxon
pKa (Strongest Basic)	3.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.84 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.51 m³·mol⁻¹	ChemAxon
Polarizability	26.24 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]+	160.28	30932474
DeepCCS	[M-H]-	157.922	30932474
DeepCCS	[M-2H]-	190.808	30932474
DeepCCS	[M+Na]+	166.373	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	152.9	32859911
AllCCS	[M+NH4]+	160.4	32859911
AllCCS	[M+Na]+	161.4	32859911
AllCCS	[M-H]-	159.4	32859911
AllCCS	[M+Na-2H]-	159.2	32859911
AllCCS	[M+HCOO]-	159.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Amino-4-methoxybenzanilide	COC1=C(N)C=C(C=C1)C(O)=NC1=CC=CC=C1	3480.5	Standard polar	33892256
3-Amino-4-methoxybenzanilide	COC1=C(N)C=C(C=C1)C(O)=NC1=CC=CC=C1	2562.3	Standard non polar	33892256
3-Amino-4-methoxybenzanilide	COC1=C(N)C=C(C=C1)C(O)=NC1=CC=CC=C1	2388.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Amino-4-methoxybenzanilide,2TMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C)C=C1N[Si](C)(C)C	2467.5	Semi standard non polar	33892256
3-Amino-4-methoxybenzanilide,2TMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C)C=C1N[Si](C)(C)C	2436.5	Standard non polar	33892256
3-Amino-4-methoxybenzanilide,2TMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C)C=C1N[Si](C)(C)C	2997.8	Standard polar	33892256
3-Amino-4-methoxybenzanilide,2TMS,isomer #2	COC1=CC=C(C(O)=NC2=CC=CC=C2)C=C1N([Si](C)(C)C)[Si](C)(C)C	2496.5	Semi standard non polar	33892256
3-Amino-4-methoxybenzanilide,2TMS,isomer #2	COC1=CC=C(C(O)=NC2=CC=CC=C2)C=C1N([Si](C)(C)C)[Si](C)(C)C	2465.8	Standard non polar	33892256
3-Amino-4-methoxybenzanilide,2TMS,isomer #2	COC1=CC=C(C(O)=NC2=CC=CC=C2)C=C1N([Si](C)(C)C)[Si](C)(C)C	3011.2	Standard polar	33892256
3-Amino-4-methoxybenzanilide,3TMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C)C=C1N([Si](C)(C)C)[Si](C)(C)C	2367.5	Semi standard non polar	33892256
3-Amino-4-methoxybenzanilide,3TMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C)C=C1N([Si](C)(C)C)[Si](C)(C)C	2396.9	Standard non polar	33892256
3-Amino-4-methoxybenzanilide,3TMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C)C=C1N([Si](C)(C)C)[Si](C)(C)C	2856.8	Standard polar	33892256
3-Amino-4-methoxybenzanilide,2TBDMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C1N[Si](C)(C)C(C)(C)C	2859.3	Semi standard non polar	33892256
3-Amino-4-methoxybenzanilide,2TBDMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C1N[Si](C)(C)C(C)(C)C	2856.5	Standard non polar	33892256
3-Amino-4-methoxybenzanilide,2TBDMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C1N[Si](C)(C)C(C)(C)C	3176.2	Standard polar	33892256
3-Amino-4-methoxybenzanilide,2TBDMS,isomer #2	COC1=CC=C(C(O)=NC2=CC=CC=C2)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2922.8	Semi standard non polar	33892256
3-Amino-4-methoxybenzanilide,2TBDMS,isomer #2	COC1=CC=C(C(O)=NC2=CC=CC=C2)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2903.1	Standard non polar	33892256
3-Amino-4-methoxybenzanilide,2TBDMS,isomer #2	COC1=CC=C(C(O)=NC2=CC=CC=C2)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3138.2	Standard polar	33892256
3-Amino-4-methoxybenzanilide,3TBDMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2989.5	Semi standard non polar	33892256
3-Amino-4-methoxybenzanilide,3TBDMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3063.7	Standard non polar	33892256
3-Amino-4-methoxybenzanilide,3TBDMS,isomer #1	COC1=CC=C(C(=NC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3123.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Amino-4-methoxybenzanilide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fdp-5930000000-43ef40724f10fa14d938	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Amino-4-methoxybenzanilide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Amino-4-methoxybenzanilide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Amino-4-methoxybenzanilide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Amino-4-methoxybenzanilide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Amino-4-methoxybenzanilide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 3-Amino-4-methoxybenzanilide 10V, Positive-QTOF	splash10-0006-1090000000-20db7b852a68746ea4c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-4-methoxybenzanilide 20V, Positive-QTOF	splash10-0006-4490000000-00c5dddf7675fcd8db4a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-4-methoxybenzanilide 40V, Positive-QTOF	splash10-00r6-9300000000-7a25ac86f618b8f5471b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-4-methoxybenzanilide 10V, Negative-QTOF	splash10-0006-0090000000-7a3d6599fa386570ce63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-4-methoxybenzanilide 20V, Negative-QTOF	splash10-0006-0490000000-da5a7bc83077ff4d3f4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-4-methoxybenzanilide 40V, Negative-QTOF	splash10-0006-7910000000-4ef2f06b531be909148a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-4-methoxybenzanilide 10V, Positive-QTOF	splash10-0006-0090000000-b95f1c2b8c6e4595777e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-4-methoxybenzanilide 20V, Positive-QTOF	splash10-006x-0980000000-14486d9dee0b32bed37f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-4-methoxybenzanilide 40V, Positive-QTOF	splash10-00di-6900000000-79613f6c264c5fbf43a7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-4-methoxybenzanilide 10V, Negative-QTOF	splash10-0006-0090000000-89e0cbe5eca3165b8904	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-4-methoxybenzanilide 20V, Negative-QTOF	splash10-0a4l-1930000000-6abfd0f77831f2469b45	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Amino-4-methoxybenzanilide 40V, Negative-QTOF	splash10-052f-8920000000-ebd317e81b5efaa16382	2021-10-12	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

8119

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8426

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 3-Amino-4-methoxybenzanilide (HMDB0245807)

MOL for HMDB0245807 (3-Amino-4-methoxybenzanilide)

3D MOL for HMDB0245807 (3-Amino-4-methoxybenzanilide)

3D SDF for HMDB0245807 (3-Amino-4-methoxybenzanilide)

3D-SDF for HMDB0245807 (3-Amino-4-methoxybenzanilide)

PDB for HMDB0245807 (3-Amino-4-methoxybenzanilide)

3D PDB for HMDB0245807 (3-Amino-4-methoxybenzanilide)

SMILES for HMDB0245807 (3-Amino-4-methoxybenzanilide)

INCHI for HMDB0245807 (3-Amino-4-methoxybenzanilide)

Structure for HMDB0245807 (3-Amino-4-methoxybenzanilide)

3D Structure for HMDB0245807 (3-Amino-4-methoxybenzanilide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra