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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:44:40 UTC

Update Date

2021-09-26 22:52:26 UTC

HMDB ID

HMDB0244596

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester

Description

Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester, also known as tyrphostin AG957 or methyl 4-{[(2,5-dihydroxyphenyl)methyl]amino}benzoic acid, belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine. Based on a literature review very few articles have been published on Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester 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

HMDB0244596
     RDKit          3D
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester
 35 36  0  0  0  0  0  0  0  0999 V2000
    6.1325    1.8166   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9825    1.1116   -0.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574   -0.2516   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6681   -1.0459   -0.1500 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3195   -0.6361    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4831    0.3657    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1322    0.1411    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5986   -1.0822    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617   -1.1442    0.0027 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383   -1.3526    0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9119   -0.3813    0.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    0.9564    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856    1.8521    0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753    3.2030    0.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9692    1.2914   -0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0856   -0.0790   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0427   -0.8951   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0851   -2.2275   -0.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675   -2.0822   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215   -1.8263   -0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0259    1.3699   -0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3452    1.9257   -1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0433    2.8710   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8669    1.2966    0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3984    0.9099    0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1008   -1.0148   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788   -2.3437    1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5430   -0.9221    1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9872    1.3931    1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3810    3.9408    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8217    1.8838   -0.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585   -0.4667   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4024   -2.9379   -0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -3.0137   -0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5113   -2.6261   -0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  8 19  1  0
 19 20  2  0
 20  5  1  0
 17 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

  Mrv1652309102123442D          

 20 21  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
 14 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244596

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1=CC=C(NCC2=C(O)C=CC(O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H15NO4/c1-20-15(19)10-2-4-12(5-3-10)16-9-11-8-13(17)6-7-14(11)18/h2-8,16-18H,9H2,1H3

> <INCHI_KEY>
QSFREBZMBNRGOK-UHFFFAOYSA-N

> <FORMULA>
C15H15NO4

> <MOLECULAR_WEIGHT>
273.288

> <EXACT_MASS>
273.100107967

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.84064018381457

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-{[(2,5-dihydroxyphenyl)methyl]amino}benzoate

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.5668433813333333

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.354033598868499

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.458899516707255

> <JCHEM_PKA_STRONGEST_BASIC>
2.279988041132257

> <JCHEM_POLAR_SURFACE_AREA>
78.79

> <JCHEM_REFRACTIVITY>
76.8515

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-{[(2,5-dihydroxyphenyl)methyl]amino}benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244596
     RDKit          3D
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester
 35 36  0  0  0  0  0  0  0  0999 V2000
    6.1325    1.8166   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9825    1.1116   -0.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574   -0.2516   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6681   -1.0459   -0.1500 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3195   -0.6361    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4831    0.3657    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1322    0.1411    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5986   -1.0822    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617   -1.1442    0.0027 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383   -1.3526    0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9119   -0.3813    0.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    0.9564    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856    1.8521    0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753    3.2030    0.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9692    1.2914   -0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0856   -0.0790   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0427   -0.8951   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0851   -2.2275   -0.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675   -2.0822   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215   -1.8263   -0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0259    1.3699   -0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3452    1.9257   -1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0433    2.8710   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8669    1.2966    0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3984    0.9099    0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1008   -1.0148   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788   -2.3437    1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5430   -0.9221    1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9872    1.3931    1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3810    3.9408    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8217    1.8838   -0.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585   -0.4667   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4024   -2.9379   -0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -3.0137   -0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5113   -2.6261   -0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  8 19  1  0
 19 20  2  0
 20  5  1  0
 17 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.667  -9.240   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17                                                            
CONECT   20   14                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0244596
HETATM    1  C1  UNL     1       6.133   1.817  -0.484  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.983   1.112  -0.218  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.757  -0.252  -0.079  1.00  0.00           C  
HETATM    4  O2  UNL     1       5.668  -1.046  -0.150  1.00  0.00           O  
HETATM    5  C3  UNL     1       3.320  -0.636   0.150  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.483   0.366   0.579  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.132   0.141   0.572  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.599  -1.082   0.135  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.762  -1.144   0.003  1.00  0.00           N  
HETATM   10  C7  UNL     1      -1.838  -1.353   0.896  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.912  -0.381   0.486  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.857   0.956   0.740  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.886   1.852   0.407  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.775   3.203   0.697  1.00  0.00           O  
HETATM   15  C11 UNL     1      -4.969   1.291  -0.205  1.00  0.00           C  
HETATM   16  C12 UNL     1      -5.086  -0.079  -0.488  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.043  -0.895  -0.130  1.00  0.00           C  
HETATM   18  O4  UNL     1      -4.085  -2.227  -0.393  1.00  0.00           O  
HETATM   19  C14 UNL     1       1.468  -2.082  -0.285  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.822  -1.826  -0.264  1.00  0.00           C  
HETATM   21  H1  UNL     1       7.026   1.370  -0.057  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.345   1.926  -1.583  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.043   2.871  -0.099  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.867   1.297   0.911  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.398   0.910   0.903  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.101  -1.015  -1.054  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.179  -2.344   1.101  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.543  -0.922   1.939  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.987   1.393   1.248  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.381   3.941   0.542  1.00  0.00           H  
HETATM   31  H11 UNL     1      -5.822   1.884  -0.510  1.00  0.00           H  
HETATM   32  H12 UNL     1      -5.958  -0.467  -0.997  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.402  -2.938  -0.226  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.032  -3.014  -0.610  1.00  0.00           H  
HETATM   35  H15 UNL     1       3.511  -2.626  -0.602  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   20
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   19
CONECT    9   10   26
CONECT   10   11   27   28
CONECT   11   12   12   17
CONECT   12   13   29
CONECT   13   14   15   15
CONECT   14   30
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18
CONECT   18   33
CONECT   19   20   20   34
CONECT   20   35
END

HMDB0244596
     RDKit          3D
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester
 35 36  0  0  0  0  0  0  0  0999 V2000
    6.1325    1.8166   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9825    1.1116   -0.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574   -0.2516   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6681   -1.0459   -0.1500 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3195   -0.6361    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4831    0.3657    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1322    0.1411    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5986   -1.0822    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617   -1.1442    0.0027 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383   -1.3526    0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9119   -0.3813    0.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    0.9564    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856    1.8521    0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753    3.2030    0.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9692    1.2914   -0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0856   -0.0790   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0427   -0.8951   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0851   -2.2275   -0.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675   -2.0822   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215   -1.8263   -0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0259    1.3699   -0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3452    1.9257   -1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0433    2.8710   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8669    1.2966    0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3984    0.9099    0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1008   -1.0148   -1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788   -2.3437    1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5430   -0.9221    1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9872    1.3931    1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3810    3.9408    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8217    1.8838   -0.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585   -0.4667   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4024   -2.9379   -0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -3.0137   -0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5113   -2.6261   -0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  8 19  1  0
 19 20  2  0
 20  5  1  0
 17 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Benzoate, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester	Generator
Methyl 4-{[(2,5-dihydroxyphenyl)methyl]amino}benzoic acid	HMDB
Tyrphostin ag957	HMDB

Chemical Formula

C₁₅H₁₅NO₄

Average Molecular Weight

273.288

Monoisotopic Molecular Weight

273.100107967

IUPAC Name

methyl 4-{[(2,5-dihydroxyphenyl)methyl]amino}benzoate

Traditional Name

methyl 4-{[(2,5-dihydroxyphenyl)methyl]amino}benzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC=C(NCC2=C(O)C=CC(O)=C2)C=C1

InChI Identifier

InChI=1S/C15H15NO4/c1-20-15(19)10-2-4-12(5-3-10)16-9-11-8-13(17)6-7-14(11)18/h2-8,16-18H,9H2,1H3

InChI Key

QSFREBZMBNRGOK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylbenzamines

Alternative Parents

Substituents

Phenylbenzamine
Aminobenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Benzylamine
Hydroquinone
Phenylalkylamine
Aniline or substituted anilines
1-hydroxy-2-unsubstituted benzenoid
Phenol
Secondary aliphatic/aromatic amine
Aralkylamine
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Secondary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.9	ALOGPS
logP	2.57	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	2.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.79 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	76.85 m³·mol⁻¹	ChemAxon
Polarizability	28.84 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]+	167.834	30932474
DeepCCS	[M-H]-	165.476	30932474
DeepCCS	[M-2H]-	198.363	30932474
DeepCCS	[M+Na]+	173.928	30932474
AllCCS	[M+H]+	163.4	32859911
AllCCS	[M+H-H2O]+	159.8	32859911
AllCCS	[M+NH4]+	166.7	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	165.9	32859911
AllCCS	[M+Na-2H]-	165.6	32859911
AllCCS	[M+HCOO]-	165.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester	COC(=O)C1=CC=C(NCC2=C(O)C=CC(O)=C2)C=C1	3673.6	Standard polar	33892256
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester	COC(=O)C1=CC=C(NCC2=C(O)C=CC(O)=C2)C=C1	2746.1	Standard non polar	33892256
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester	COC(=O)C1=CC=C(NCC2=C(O)C=CC(O)=C2)C=C1	2882.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester,3TMS,isomer #1	COC(=O)C1=CC=C(N(CC2=CC(O[Si](C)(C)C)=CC=C2O[Si](C)(C)C)[Si](C)(C)C)C=C1	2726.8	Semi standard non polar	33892256
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester,3TMS,isomer #1	COC(=O)C1=CC=C(N(CC2=CC(O[Si](C)(C)C)=CC=C2O[Si](C)(C)C)[Si](C)(C)C)C=C1	2700.0	Standard non polar	33892256
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester,3TMS,isomer #1	COC(=O)C1=CC=C(N(CC2=CC(O[Si](C)(C)C)=CC=C2O[Si](C)(C)C)[Si](C)(C)C)C=C1	2783.3	Standard polar	33892256
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester,3TBDMS,isomer #1	COC(=O)C1=CC=C(N(CC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3363.4	Semi standard non polar	33892256
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester,3TBDMS,isomer #1	COC(=O)C1=CC=C(N(CC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3256.9	Standard non polar	33892256
Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester,3TBDMS,isomer #1	COC(=O)C1=CC=C(N(CC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3086.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-0790000000-ca346267e042ec5f870b	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester GC-MS (TBDMS_2_3) - 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 - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester 10V, Positive-QTOF	splash10-00di-0390000000-accd2f929e6db819f7c5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester 20V, Positive-QTOF	splash10-00di-1920000000-30a25488165b3054bad5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester 40V, Positive-QTOF	splash10-00di-8900000000-6bc6ba07533cbe07707d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester 10V, Negative-QTOF	splash10-0fk9-3590000000-6804c021119ab9b3d88e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester 20V, Negative-QTOF	splash10-00di-1950000000-b3acb3a80c121216bbcd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester 40V, Negative-QTOF	splash10-0006-9710000000-2c5106ee1795bf7ea481	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

1980

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2064

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 Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester (HMDB0244596)

MOL for HMDB0244596 (Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester)

3D MOL for HMDB0244596 (Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester)

3D SDF for HMDB0244596 (Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester)

3D-SDF for HMDB0244596 (Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester)

PDB for HMDB0244596 (Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester)

3D PDB for HMDB0244596 (Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester)

SMILES for HMDB0244596 (Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester)

INCHI for HMDB0244596 (Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester)

Structure for HMDB0244596 (Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester)

3D Structure for HMDB0244596 (Benzoic acid, 4-[[(2,5-dihydroxyphenyl)methyl]amino]-, methyl ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra