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Showing metabocard for Dimethyl phthalate (HMDB0251388)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:44:49 UTC
Update Date2021-09-26 23:03:22 UTC
HMDB IDHMDB0251388
Secondary Accession NumbersNone
Metabolite Identification
Common NameDimethyl phthalate
DescriptionDimethylphthalate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Phthalate esters are endocrine disruptors. Dimethylphthalate is an extremely weak basic (essentially neutral) compound (based on its pKa). The terminal or next-to-last carbon atom in the monoester can also be oxidized to an alcohol, which can be excreted as is or first oxidized to an aldehyde, ketone, or carboxylic acid. Dimethylphthalate is a potentially toxic compound. Phthalate esters are esters of phthalic acid and are mainly used as plasticizers, primarily used to soften polyvinyl chloride. They decrease foetal testis testosterone production and reduce the expression of steroidogenic genes by decreasing mRNA expression. Phthalates are hazardous due to their ability to act as endocrine disruptors. The combination of effects associated with phthalates is called 'phthalate syndrome’. Phthalate esters are first hydrolyzed to their monoester derivative. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dimethyl phthalate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dimethyl phthalate 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0251388 (Dimethyl phthalate)

  Mrv0541 02241205462D          

 14 14  0  0  0  0            999 V2000
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
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3D MOL for HMDB0251388 (Dimethyl phthalate)

HMDB0251388
     RDKit          3D
Dimethyl phthalate
 24 24  0  0  0  0  0  0  0  0999 V2000
   -3.4548    2.2037   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7968    0.9773   -0.1901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3845    0.8792   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8040    1.9297   -0.3828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7359   -0.3944    0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6133   -1.4792    0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1003   -2.7112    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2602   -2.9429    0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -1.8754    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6150   -0.5721    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5588    0.4949   -0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838    1.6823   -0.3323 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9276    0.1141   -0.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9668    1.0723   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6701    2.3618   -1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4393    2.1456    0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910    3.0686   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6678   -1.3111    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7387   -3.5952    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444   -3.9262    0.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1589   -2.0512    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083    2.0586   -0.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    0.9695   -1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8150    0.9012    0.4899 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  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 10  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
 14 22  1  0
 14 23  1  0
 14 24  1  0
M  END
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3D SDF for HMDB0251388 (Dimethyl phthalate)

  Mrv0541 02241205462D          

 14 14  0  0  0  0            999 V2000
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251388

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H,1-2H3

> <INCHI_KEY>
NIQCNGHVCWTJSM-UHFFFAOYSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.184

> <EXACT_MASS>
194.057908808

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.39433544792789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2-dimethyl benzene-1,2-dicarboxylate

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
1.980199744

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.6480462547141626

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
50.10860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethyl phthalate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0251388 (Dimethyl phthalate)

HMDB0251388
     RDKit          3D
Dimethyl phthalate
 24 24  0  0  0  0  0  0  0  0999 V2000
   -3.4548    2.2037   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7968    0.9773   -0.1901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3845    0.8792   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8040    1.9297   -0.3828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7359   -0.3944    0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6133   -1.4792    0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1003   -2.7112    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2602   -2.9429    0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -1.8754    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6150   -0.5721    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5588    0.4949   -0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838    1.6823   -0.3323 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9276    0.1141   -0.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9668    1.0723   -0.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6701    2.3618   -1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4393    2.1456    0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910    3.0686   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6678   -1.3111    0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7387   -3.5952    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444   -3.9262    0.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1589   -2.0512    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083    2.0586   -0.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    0.9695   -1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8150    0.9012    0.4899 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  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 10  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  0
 14 22  1  0
 14 23  1  0
 14 24  1  0
M  END
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PDB for HMDB0251388 (Dimethyl phthalate)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+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                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for HMDB0251388 (Dimethyl phthalate)

COMPND    HMDB0251388
HETATM    1  C1  UNL     1      -3.455   2.204  -0.439  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.797   0.977  -0.190  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.385   0.879  -0.170  1.00  0.00           C  
HETATM    4  O2  UNL     1      -0.804   1.930  -0.383  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.736  -0.394   0.089  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.613  -1.479   0.309  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.100  -2.711   0.559  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.260  -2.943   0.606  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.091  -1.875   0.390  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.615  -0.572   0.125  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.559   0.495  -0.091  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.384   1.682  -0.332  1.00  0.00           O  
HETATM   13  O4  UNL     1       2.928   0.114  -0.014  1.00  0.00           O  
HETATM   14  C10 UNL     1       3.967   1.072  -0.208  1.00  0.00           C  
HETATM   15  H1  UNL     1      -3.670   2.362  -1.510  1.00  0.00           H  
HETATM   16  H2  UNL     1      -4.439   2.146   0.074  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.891   3.069  -0.032  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.668  -1.311   0.274  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.739  -3.595   0.738  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.644  -3.926   0.806  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.159  -2.051   0.426  1.00  0.00           H  
HETATM   22  H8  UNL     1       3.508   2.059  -0.047  1.00  0.00           H  
HETATM   23  H9  UNL     1       4.366   0.969  -1.246  1.00  0.00           H  
HETATM   24  H10 UNL     1       4.815   0.901   0.490  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   10
CONECT    6    7   18
CONECT    7    8    8   19
CONECT    8    9   20
CONECT    9   10   10   21
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   22   23   24
END
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SMILES for HMDB0251388 (Dimethyl phthalate)

COC(=O)C1=CC=CC=C1C(=O)OC
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INCHI for HMDB0251388 (Dimethyl phthalate)

InChI=1S/C10H10O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Dimethylphthalic acidGenerator
Methyl phthalateChEMBL
Methyl phthalic acidGenerator
Dimethyl phthalic acidGenerator
Dimethyl phthalate, conjugate diacidMeSH
DimethylphthalateMeSH
Chemical FormulaC10H10O4
Average Molecular Weight194.184
Monoisotopic Molecular Weight194.057908808
IUPAC Name1,2-dimethyl benzene-1,2-dicarboxylate
Traditional Namedimethyl phthalate
CAS Registry NumberNot Available
SMILES
COC(=O)C1=CC=CC=C1C(=O)OC
InChI Identifier
InChI=1S/C10H10O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H,1-2H3
InChI KeyNIQCNGHVCWTJSM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13336
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11233
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimethyl phthalate
METLIN IDNot Available
PubChem Compound8554
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]