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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2014-09-22 19:36:08 UTC

Update Date

2020-11-09 23:22:07 UTC

HMDB ID

HMDB0061744

Secondary Accession Numbers

HMDB61744

Metabolite Identification

Common Name

Mono-benzyl phthalate

Description

Mono-benzyl phthalate, also known as benzene-1,2-dicarboxylic acid, monobenzyl ester or benzyl hydrogen phthalate, is a metabolite of butyl benzyl phthalate (BBzP). It can be found in human biofluids. Phthalates are industrial chemicals that are added to plastics to impart flexibility and resilience and are often referred to as plasticizers. Phthalates also are used as solubilizing or stabilizing agents in other applications. There are numerous products that may contain phthalates: adhesives; automotive plastics; detergents; lubricating oils; some medical devices and pharmaceuticals; plastic raincoats; solvents; vinyl tiles and flooring; and personal-care products, such as soap, shampoo, deodorants, lotions, fragrances, hair spray, and nail polish. Phthalates are often used in polyvinyl chloride type plastics, such as plastic packaging film and sheet, garden hoses, inflatable recreational toys, blood product storage bags, intravenous medical tubing, and toys. Because they are not chemically bound to the plastics to which they are added, phthalates can be released into the environment during use or disposal of the product. People are exposed to phthalates through ingestion, inhalation, and, to a lesser extent, dermal contact with products that contain phthalates. Phthalates have low acute animal toxicity. In animals, phthalates produced anti-androgenic effects by reducing testosterone production and, at very high levels, reducing estrogen production, effects that may be mediated by inhibiting testicular and ovarian steroidogenesis. (ChemoSummarizer)

Structure

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

HMDB0061744
     RDKit          3D
Mono-benzyl phthalate
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.9986    1.4177    1.6969 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7522    1.2345    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9102    2.1262    1.9540 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    0.1335    0.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490   -0.6931    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2170   -1.7448   -0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9166   -2.0293   -1.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052   -1.2337   -0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1089   -0.1237    0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9555    0.6392    0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9226    1.6137    1.3387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3363    0.2421    0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4717    1.0071    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7138    0.4508    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4793   -0.5198    0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6353   -1.0299    0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0837   -0.5626   -1.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3268    0.4080   -1.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648    0.9118   -1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0845    3.1031    2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524   -0.4431    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9867   -2.3982   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7131   -2.8751   -1.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9006   -1.4572   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497    2.0768    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5090    0.8946    1.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1397   -0.8892    1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2437   -1.7897    0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9887   -0.9411   -1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6420    0.7973   -2.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5804    1.6742   -1.7086 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  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9  4  1  0
 19 14  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
 13 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

  Mrv0541 08291400302D          

 19 20  0  0  0  0            999 V2000
    2.8579    3.3000    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
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    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
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.2500    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 14  1  0  0  0  0
 18 15  2  0  0  0  0
 19 10  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061744

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c16-14(17)12-8-4-5-9-13(12)15(18)19-10-11-6-2-1-3-7-11/h1-9H,10H2,(H,16,17)

> <INCHI_KEY>
XIKIUQUXDNHBFR-UHFFFAOYSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.2534

> <EXACT_MASS>
256.073558872

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.13226395101809

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(benzyloxy)carbonyl]benzoic acid

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
3.3587788053333325

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0835368339699447

> <JCHEM_PKA_STRONGEST_BASIC>
-6.966772627111659

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
69.9521

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(benzyloxy)carbonyl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061744
     RDKit          3D
Mono-benzyl phthalate
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.9986    1.4177    1.6969 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7522    1.2345    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9102    2.1262    1.9540 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    0.1335    0.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490   -0.6931    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2170   -1.7448   -0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9166   -2.0293   -1.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052   -1.2337   -0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1089   -0.1237    0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9555    0.6392    0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9226    1.6137    1.3387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3363    0.2421    0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4717    1.0071    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7138    0.4508    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4793   -0.5198    0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6353   -1.0299    0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0837   -0.5626   -1.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3268    0.4080   -1.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648    0.9118   -1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0845    3.1031    2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524   -0.4431    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9867   -2.3982   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7131   -2.8751   -1.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9006   -1.4572   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497    2.0768    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5090    0.8946    1.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1397   -0.8892    1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2437   -1.7897    0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9887   -0.9411   -1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6420    0.7973   -2.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5804    1.6742   -1.7086 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  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9  4  1  0
 19 14  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
 13 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  15.400   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  15.400   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  10.780   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.669  10.780   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335  13.860   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    8                                                       
CONECT    5    4    9                                                       
CONECT    6    2   11                                                       
CONECT    7    3   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   13                                                       
CONECT   10   11   19                                                       
CONECT   11    6    7   10                                                  
CONECT   12    8   13   14                                                  
CONECT   13    9   12   15                                                  
CONECT   14   12   16   17                                                  
CONECT   15   13   18   19                                                  
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19   10   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0061744
HETATM    1  O1  UNL     1       4.999   1.418   1.697  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.752   1.235   1.403  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.910   2.126   1.954  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.392   0.133   0.543  1.00  0.00           C  
HETATM    5  C3  UNL     1       4.449  -0.693   0.062  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.217  -1.745  -0.747  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.917  -2.029  -1.121  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.905  -1.234  -0.657  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.109  -0.124   0.192  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.956   0.639   0.616  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.923   1.614   1.339  1.00  0.00           O  
HETATM   12  O4  UNL     1      -0.336   0.242   0.158  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.472   1.007   0.585  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.714   0.451   0.014  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.479  -0.520   0.625  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.635  -1.030   0.081  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.084  -0.563  -1.150  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.327   0.408  -1.770  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.165   0.912  -1.210  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.085   3.103   2.149  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.452  -0.443   0.373  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.987  -2.398  -1.135  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.713  -2.875  -1.774  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.901  -1.457  -0.948  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.350   2.077   0.327  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.509   0.895   1.689  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.140  -0.889   1.580  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.244  -1.790   0.549  1.00  0.00           H  
HETATM   29  H10 UNL     1      -5.989  -0.941  -1.607  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.642   0.797  -2.728  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.580   1.674  -1.709  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   11   12
CONECT   12   13
CONECT   13   14   25   26
CONECT   14   15   15   19
CONECT   15   16   27
CONECT   16   17   17   28
CONECT   17   18   29
CONECT   18   19   19   30
CONECT   19   31
END

HMDB0061744
     RDKit          3D
Mono-benzyl phthalate
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.9986    1.4177    1.6969 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7522    1.2345    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9102    2.1262    1.9540 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    0.1335    0.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490   -0.6931    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2170   -1.7448   -0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9166   -2.0293   -1.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052   -1.2337   -0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1089   -0.1237    0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9555    0.6392    0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9226    1.6137    1.3387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3363    0.2421    0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4717    1.0071    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7138    0.4508    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4793   -0.5198    0.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6353   -1.0299    0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0837   -0.5626   -1.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3268    0.4080   -1.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648    0.9118   -1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0845    3.1031    2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4524   -0.4431    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9867   -2.3982   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7131   -2.8751   -1.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9006   -1.4572   -0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497    2.0768    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5090    0.8946    1.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1397   -0.8892    1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2437   -1.7897    0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9887   -0.9411   -1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6420    0.7973   -2.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5804    1.6742   -1.7086 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  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9  4  1  0
 19 14  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
 13 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Benzenedicarboxylic acid, mono(phenylmethyl) ester	ChEBI
Benzene-1,2-dicarboxylic acid, mono(phenylmethyl) ester	ChEBI
Benzene-1,2-dicarboxylic acid, monobenzyl ester	ChEBI
Benzyl hydrogen phthalate	ChEBI
MBeP	ChEBI
mono(Phenylmethyl) 1,2-benzenedicarboxylate	ChEBI
O-(Benzyloxycarbonyl)benzoic acid	ChEBI
1,2-Benzenedicarboxylate, mono(phenylmethyl) ester	Generator
Benzene-1,2-dicarboxylate, mono(phenylmethyl) ester	Generator
Benzene-1,2-dicarboxylate, monobenzyl ester	Generator
Benzyl hydrogen phthalic acid	Generator
mono(Phenylmethyl) 1,2-benzenedicarboxylic acid	Generator
O-(Benzyloxycarbonyl)benzoate	Generator
mono-Benzyl phthalic acid	Generator
Phthalic acid monobenzyl ester	HMDB
mono-Benzyl phthalate, calcium salt	HMDB

Chemical Formula

C₁₅H₁₂O₄

Average Molecular Weight

256.2534

Monoisotopic Molecular Weight

256.073558872

IUPAC Name

2-[(benzyloxy)carbonyl]benzoic acid

Traditional Name

2-[(benzyloxy)carbonyl]benzoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1

InChI Identifier

InChI=1S/C15H12O4/c16-14(17)12-8-4-5-9-13(12)15(18)19-10-11-6-2-1-3-7-11/h1-9H,10H2,(H,16,17)

InChI Key

XIKIUQUXDNHBFR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzyloxycarbonyl
Benzoate ester
Benzoic acid
Benzoyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Membrane (HMDB: HMDB0061744)

Biofluid or Excreta

Biofluid and excreta (HMDB: HMDB0061744)

Source

Exogenous

Exogenous (HMDB: HMDB0061744)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Mono-benzyl phthalate Exposure (MarkerDB: MDB00029811)

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	2.85	ALOGPS
logP	3.36	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.95 m³·mol⁻¹	ChemAxon
Polarizability	26.13 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
DarkChem	[M+H]+	157.995	31661259
DarkChem	[M-H]-	157.151	31661259
DeepCCS	[M+H]+	158.332	30932474
DeepCCS	[M-H]-	155.937	30932474
DeepCCS	[M-2H]-	189.038	30932474
DeepCCS	[M+Na]+	164.379	30932474
AllCCS	[M+H]+	157.6	32859911
AllCCS	[M+H-H2O]+	153.8	32859911
AllCCS	[M+NH4]+	161.1	32859911
AllCCS	[M+Na]+	162.1	32859911
AllCCS	[M-H]-	159.3	32859911
AllCCS	[M+Na-2H]-	158.8	32859911
AllCCS	[M+HCOO]-	158.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mono-benzyl phthalate	OC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1	3394.9	Standard polar	33892256
Mono-benzyl phthalate	OC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1	2155.6	Standard non polar	33892256
Mono-benzyl phthalate	OC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1	2203.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mono-benzyl phthalate,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1	2213.3	Semi standard non polar	33892256
Mono-benzyl phthalate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1	2438.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mono-benzyl phthalate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-1f572ba8708abb7b299c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mono-benzyl phthalate GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9340000000-46be518d8fe3daa54ec8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mono-benzyl phthalate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate LC-ESI-ITFT , negative-QTOF	splash10-0560-3900000000-aaa9182012f2cd8dccc3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate LC-ESI-ITFT , negative-QTOF	splash10-0a4i-3900000000-c7c291e22885d7da56fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate LC-ESI-ITFT , negative-QTOF	splash10-001i-0910000000-361ba129494110a999dd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate LC-ESI-ITFT , negative-QTOF	splash10-001i-0910000000-96e016407b07c7790374	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate LC-ESI-QFT , negative-QTOF	splash10-0a59-0970000000-fa1c2407813f2b87e224	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate LC-ESI-ITFT , positive-QTOF	splash10-0006-9000000000-bab392b0bbcf1cba23df	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate LC-ESI-ITFT , positive-QTOF	splash10-0006-9000000000-bab392b0bbcf1cba23df	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate LC-ESI-ITFT , positive-QTOF	splash10-0006-9000000000-bd402d4f782b50a53d61	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate LC-ESI-ITFT , positive-QTOF	splash10-0006-9000000000-dcf44f373c2d0dbd1993	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate LC-ESI-QFT , positive-QTOF	splash10-0006-9000000000-fc0a770769824e31a85e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate 90V, Negative-QTOF	splash10-004i-9100000000-ae466f97ea8aa7db383f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate 75V, Negative-QTOF	splash10-004i-9400000000-e233c23db1ce5f1fecb9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate 55V, Positive-QTOF	splash10-0006-9000000000-bab392b0bbcf1cba23df	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate 35V, Negative-QTOF	splash10-001i-0910000000-361ba129494110a999dd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate 80V, Negative-QTOF	splash10-0a4i-3900000000-c7c291e22885d7da56fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate 35V, Positive-QTOF	splash10-0006-9000000000-fc0a770769824e31a85e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate 55V, Negative-QTOF	splash10-0560-3900000000-aaa9182012f2cd8dccc3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate 55V, Negative-QTOF	splash10-001i-0910000000-96e016407b07c7790374	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mono-benzyl phthalate 35V, Negative-QTOF	splash10-0a59-0970000000-3fe29b31da509e6d5650	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-benzyl phthalate 10V, Positive-QTOF	splash10-0a4l-3290000000-ab7fdcb8a09b6a431ac9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-benzyl phthalate 20V, Positive-QTOF	splash10-0006-9560000000-9e7bcf95080e1af6850b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-benzyl phthalate 40V, Positive-QTOF	splash10-052f-9600000000-9083118be5c3881008c9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-benzyl phthalate 10V, Negative-QTOF	splash10-0a4i-0290000000-4593ee91b285fedcd547	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-benzyl phthalate 20V, Negative-QTOF	splash10-0odi-2960000000-b3aa9a3851dc0a82408a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-benzyl phthalate 40V, Negative-QTOF	splash10-00b9-8900000000-c0e4a8cd23485ac1c581	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.00280 (0.00253-0.00310) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.00666 (0.00560-0.00794) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

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

31736

PDB ID

Not Available

ChEBI ID

132612

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029811

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Brock JW, Bell JM, Guillette LJ Jr: Urinary Phthalate Metabolites in American Alligators (Alligator mississippiensis) from Selected Florida Wetlands. Arch Environ Contam Toxicol. 2016 Jul;71(1):1-6. doi: 10.1007/s00244-015-0260-6. Epub 2016 Jan 7. [PubMed:26743198 ]

Showing metabocard for Mono-benzyl phthalate (HMDB0061744)

MOL for HMDB0061744 (Mono-benzyl phthalate)

3D MOL for HMDB0061744 (Mono-benzyl phthalate)

3D SDF for HMDB0061744 (Mono-benzyl phthalate)

3D-SDF for HMDB0061744 (Mono-benzyl phthalate)

PDB for HMDB0061744 (Mono-benzyl phthalate)

3D PDB for HMDB0061744 (Mono-benzyl phthalate)

SMILES for HMDB0061744 (Mono-benzyl phthalate)

INCHI for HMDB0061744 (Mono-benzyl phthalate)

Structure for HMDB0061744 (Mono-benzyl phthalate)

3D Structure for HMDB0061744 (Mono-benzyl phthalate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra