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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-30 15:51:40 UTC

Update Date

2021-09-14 15:45:46 UTC

HMDB ID

HMDB0013248

Secondary Accession Numbers

HMDB13248

Metabolite Identification

Common Name

Monoethylhexyl phthalic acid

Description

Monoethylhexyl phthalic acid (MEHP) is an active metabolite of Bis(2-ethylhexyl)phthalate (DEHP). DEHP measured from the blood of pregnant women have been significantly associated with the decreased penis width, shorter anogenital distance, and the incomplete descent of testes of their newborn sons, replicating effects identified in animals(Wikipedia). DEHP hydrolyzes to MEHP via the enzyme Bis(2-ethylhexyl)phthalate acylhydrolase(3.1.1.60)and subsequently to phthalate salts. The released alcohol is susceptible to oxidation to the aldehyde and carboxylic acid.

Structure

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

HMDB0013248
     RDKit          3D
Monoethylhexyl phthalic acid
 42 42  0  0  0  0  0  0  0  0999 V2000
    4.1493    2.5426   -1.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2820    1.2730   -1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7322    0.4724   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117   -0.8173    0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052   -0.9153    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2689   -2.3679    0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -3.0037    1.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638   -0.1066   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056   -0.3084    0.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    0.4230   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1908    1.1296   -1.2915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944    0.2727    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758   -0.6049    1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393   -0.8140    1.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5985   -0.1693    0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3298    0.6746   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0304    0.9141   -0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044    1.8437   -1.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378    2.1407   -2.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0852    2.4461   -2.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0656    2.3772   -1.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5822    3.4038   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300    2.8143   -0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2691    1.5791   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    0.7335   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8613    0.3214   -0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    1.1042    0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668   -1.5632   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240   -1.2946    1.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003   -0.5007    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2290   -2.3712    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2900   -2.9521   -0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5674   -2.2235    2.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568   -3.6195    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5495   -3.6899    2.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9358    0.9770    0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349   -0.2285   -1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054   -1.1084    1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7058   -1.4858    2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6328   -0.3234    1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1518    1.2009   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6742    1.8241   -2.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  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
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 20 42  1  0
M  END

  Mrv1652302102020392D          

 20 20  0  0  0  0            999 V2000
   14.3817  -11.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3817  -12.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6671  -11.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6671  -13.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9527  -11.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9527  -12.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6671  -10.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3815  -10.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9526  -10.2430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2382  -11.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2382  -10.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5238  -11.8929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9526   -9.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2382   -9.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2382   -8.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5236   -7.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5237   -9.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8092   -9.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0947   -9.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3803   -9.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 14  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013248

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O4/c1-3-5-8-12(4-2)11-20-16(19)14-10-7-6-9-13(14)15(17)18/h6-7,9-10,12H,3-5,8,11H2,1-2H3,(H,17,18)

> <INCHI_KEY>
DJDSLBVSSOQSLW-UHFFFAOYSA-N

> <FORMULA>
C16H22O4

> <MOLECULAR_WEIGHT>
278.3435

> <EXACT_MASS>
278.151809192

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.958827582265982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[(2-ethylhexyl)oxy]carbonyl}benzoic acid

> <ALOGPS_LOGP>
4.36

> <JCHEM_LOGP>
4.656883524

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.084675782939035

> <JCHEM_PKA_STRONGEST_BASIC>
-6.956960799417961

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
77.4877

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bar 1

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013248
     RDKit          3D
Monoethylhexyl phthalic acid
 42 42  0  0  0  0  0  0  0  0999 V2000
    4.1493    2.5426   -1.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2820    1.2730   -1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7322    0.4724   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117   -0.8173    0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052   -0.9153    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2689   -2.3679    0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -3.0037    1.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638   -0.1066   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056   -0.3084    0.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    0.4230   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1908    1.1296   -1.2915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944    0.2727    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758   -0.6049    1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393   -0.8140    1.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5985   -0.1693    0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3298    0.6746   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0304    0.9141   -0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044    1.8437   -1.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378    2.1407   -2.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0852    2.4461   -2.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0656    2.3772   -1.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5822    3.4038   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300    2.8143   -0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2691    1.5791   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    0.7335   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8613    0.3214   -0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    1.1042    0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668   -1.5632   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240   -1.2946    1.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003   -0.5007    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2290   -2.3712    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2900   -2.9521   -0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5674   -2.2235    2.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568   -3.6195    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5495   -3.6899    2.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9358    0.9770    0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349   -0.2285   -1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054   -1.1084    1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7058   -1.4858    2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6328   -0.3234    1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1518    1.2009   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6742    1.8241   -2.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  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
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 20 42  1  0
M  END

HEADER    PROTEIN                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  C   UNK     0      26.846 -22.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.846 -23.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.512 -21.430   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.512 -24.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.178 -22.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.178 -23.740   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.512 -19.890   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      26.845 -19.120   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      24.178 -19.120   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      22.845 -21.430   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.845 -19.890   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      21.511 -22.200   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      24.178 -17.580   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.845 -16.810   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.845 -15.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.511 -14.500   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.511 -17.580   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.177 -16.810   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.843 -17.580   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.510 -16.810   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    7                                                  
CONECT    4    2    6                                                       
CONECT    5    3    6   10                                                  
CONECT    6    4    5                                                       
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   13                                                       
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0013248
HETATM    1  C1  UNL     1       4.149   2.543  -1.300  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.282   1.273  -1.288  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.732   0.472  -0.133  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.112  -0.817   0.172  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.705  -0.915   0.614  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.269  -2.368   0.834  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.136  -3.004   1.893  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.764  -0.107  -0.175  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.606  -0.308   0.297  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.608   0.423  -0.391  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.191   1.130  -1.292  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.994   0.273   0.023  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.276  -0.605   1.102  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.539  -0.814   1.563  1.00  0.00           C  
HETATM   15  C13 UNL     1      -5.599  -0.169   0.988  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.330   0.675  -0.049  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.030   0.914  -0.553  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.904   1.844  -1.665  1.00  0.00           C  
HETATM   19  O3  UNL     1      -2.838   2.141  -2.197  1.00  0.00           O  
HETATM   20  O4  UNL     1      -5.085   2.446  -2.171  1.00  0.00           O  
HETATM   21  H1  UNL     1       5.066   2.377  -1.885  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.582   3.404  -1.704  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.430   2.814  -0.256  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.269   1.579  -1.400  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.566   0.734  -2.249  1.00  0.00           H  
HETATM   26  H6  UNL     1       4.861   0.321  -0.256  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.692   1.104   0.806  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.267  -1.563  -0.694  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.724  -1.295   1.024  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.700  -0.501   1.696  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.229  -2.371   1.209  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.290  -2.952  -0.091  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.567  -2.224   2.566  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.957  -3.619   1.432  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.549  -3.690   2.553  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.936   0.977   0.168  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.735  -0.229  -1.240  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.405  -1.108   1.544  1.00  0.00           H  
HETATM   39  H19 UNL     1      -4.706  -1.486   2.381  1.00  0.00           H  
HETATM   40  H20 UNL     1      -6.633  -0.323   1.346  1.00  0.00           H  
HETATM   41  H21 UNL     1      -6.152   1.201  -0.526  1.00  0.00           H  
HETATM   42  H22 UNL     1      -5.674   1.824  -2.697  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6    8   30
CONECT    6    7   31   32
CONECT    7   33   34   35
CONECT    8    9   36   37
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   13   17
CONECT   13   14   38
CONECT   14   15   15   39
CONECT   15   16   40
CONECT   16   17   17   41
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   42
END

HMDB0013248
     RDKit          3D
Monoethylhexyl phthalic acid
 42 42  0  0  0  0  0  0  0  0999 V2000
    4.1493    2.5426   -1.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2820    1.2730   -1.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7322    0.4724   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117   -0.8173    0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052   -0.9153    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2689   -2.3679    0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -3.0037    1.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638   -0.1066   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056   -0.3084    0.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6079    0.4230   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1908    1.1296   -1.2915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9944    0.2727    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758   -0.6049    1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393   -0.8140    1.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5985   -0.1693    0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3298    0.6746   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0304    0.9141   -0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044    1.8437   -1.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378    2.1407   -2.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0852    2.4461   -2.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0656    2.3772   -1.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5822    3.4038   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300    2.8143   -0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2691    1.5791   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658    0.7335   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8613    0.3214   -0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    1.1042    0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668   -1.5632   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240   -1.2946    1.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003   -0.5007    1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2290   -2.3712    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2900   -2.9521   -0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5674   -2.2235    2.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568   -3.6195    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5495   -3.6899    2.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9358    0.9770    0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349   -0.2285   -1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054   -1.1084    1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7058   -1.4858    2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6328   -0.3234    1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1518    1.2009   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6742    1.8241   -2.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  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
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2-Ethylhexyl) hydrogen phthalate	ChEBI
1,2-Benzenedicarboxylic acid, mono(2-ethylhexyl) ester	ChEBI
2-([(2-Ethylhexyl)oxy]carbonyl)benzoic acid	ChEBI
2-Ethylhexyl hydrogen phthalate	ChEBI
2-Ethylhexyl phthalate	ChEBI
MEHP	ChEBI
mono(2-Ethylhexyl)phthalate	ChEBI
mono-(2-Ethylhexyl)phthalate	ChEBI
mono-2-Ethylhexyl phthalate	ChEBI
Monoethylhexyl phthalate	ChEBI
Phthalic acid, 2-ethylhexyl ester	ChEBI
(2-Ethylhexyl) hydrogen phthalic acid	Generator
1,2-Benzenedicarboxylate, mono(2-ethylhexyl) ester	Generator
2-([(2-Ethylhexyl)oxy]carbonyl)benzoate	Generator
2-Ethylhexyl hydrogen phthalic acid	Generator
2-Ethylhexyl phthalic acid	Generator
mono(2-Ethylhexyl)phthalic acid	Generator
mono-(2-Ethylhexyl)phthalic acid	Generator
mono-2-Ethylhexyl phthalic acid	Generator
Phthalate, 2-ethylhexyl ester	Generator
MEHP CPD	MeSH
mono(Ethylhexyl) phthalate	MeSH
mono-(2-Ethylhexyl)phthalate, sodium salt	MeSH
1,2-Benzenedicarboxylicacid,mono(2-ethylhexyl)ester	HMDB
mono-Ethylhexyl	HMDB
mono-Ethylhexylphthalate	HMDB
Monoethylhexyl phthalate (mehp)	HMDB
Monoethylhexylphthalate	HMDB
MONOOCTYL phthalATE	HMDB
Phthalic acid 1-hydrogen 2-(2-ethylhexyl) ester	HMDB
Phthalic acid hydrogen 1-(2-ethylhexyl) ester	HMDB
PHTHALIC ACID mono-2-ethylhexyl ester	HMDB
PHTHALIC ACID monooctyl ester	HMDB
Phthalicacid,2-ethylhexylester	HMDB
phthalicacidmono-2-ETHYLEXYLESTER	HMDB
PHTHALICACIDMONOETHYLHEXYL	HMDB
Phthalicacidmonoethylhexylester	HMDB
Monoethylhexyl phthalic acid	Generator
mono(2-Ethylhexyl) phthalic acid	Generator

Chemical Formula

C₁₆H₂₂O₄

Average Molecular Weight

278.3435

Monoisotopic Molecular Weight

278.151809192

IUPAC Name

2-{[(2-ethylhexyl)oxy]carbonyl}benzoic acid

Traditional Name

bar 1

CAS Registry Number

4376-20-9

SMILES

CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C16H22O4/c1-3-5-8-12(4-2)11-20-16(19)14-10-7-6-9-13(14)15(17)18/h6-7,9-10,12H,3-5,8,11H2,1-2H3,(H,17,18)

InChI Key

DJDSLBVSSOQSLW-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

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

dicarboxylic acid monoester (CHEBI:17243 )
phthalate ester (CHEBI:17243 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Cellular substructure

Membrane (HMDB: HMDB0013248)
Cell membrane (HMDB: HMDB0013248)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)
Sweat (HMDB: HMDB0013248)

Source

Endogenous

Endogenous (HMDB: HMDB0013248)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	4.36	ALOGPS
logP	4.66	ChemAxon
logS	-4.3	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	9	ChemAxon
Refractivity	77.49 m³·mol⁻¹	ChemAxon
Polarizability	30.96 Å³	ChemAxon
Number of Rings	1	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]+	166.51	31661259
DarkChem	[M-H]-	164.48	31661259
DeepCCS	[M+H]+	167.341	30932474
DeepCCS	[M-H]-	164.983	30932474
DeepCCS	[M-2H]-	197.868	30932474
DeepCCS	[M+Na]+	173.434	30932474
AllCCS	[M+H]+	167.5	32859911
AllCCS	[M+H-H2O]+	164.3	32859911
AllCCS	[M+NH4]+	170.5	32859911
AllCCS	[M+Na]+	171.4	32859911
AllCCS	[M-H]-	168.7	32859911
AllCCS	[M+Na-2H]-	169.2	32859911
AllCCS	[M+HCOO]-	169.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Monoethylhexyl phthalic acid	CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O	3191.0	Standard polar	33892256
Monoethylhexyl phthalic acid	CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O	1989.4	Standard non polar	33892256
Monoethylhexyl phthalic acid	CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O	2155.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Monoethylhexyl phthalic acid,1TMS,isomer #1	CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C	2135.1	Semi standard non polar	33892256
Monoethylhexyl phthalic acid,1TBDMS,isomer #1	CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2365.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Monoethylhexyl phthalic acid GC-EI-TOF (Non-derivatized)	splash10-00dj-2970000000-346112e2dd7eb2ef672f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Monoethylhexyl phthalic acid GC-EI-TOF (Non-derivatized)	splash10-00dj-2970000000-346112e2dd7eb2ef672f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monoethylhexyl phthalic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-5920000000-6756fbba86aadca647ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monoethylhexyl phthalic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7392000000-fd40ccd8c52320562e5c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monoethylhexyl phthalic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-4900000000-af0f2c76a7c01b845a00	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 30V, Positive-QTOF	splash10-006t-0960000000-efbb62fb904150b613f2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 15V, Positive-QTOF	splash10-006t-0960000000-bace63e54682391af671	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 45V, Positive-QTOF	splash10-00kb-0910000000-77eed661ab413010d354	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 60V, Positive-QTOF	splash10-00mk-0900000000-214bdb75cf5614522a03	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 45V, Negative-QTOF	splash10-00ai-0900000000-d636e4277afd375744d2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 30V, Negative-QTOF	splash10-001i-0900000000-e6f221aefc0e24f648d5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 75V, Positive-QTOF	splash10-002b-0900000000-d8cdf715271ec6e661b8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 15V, Negative-QTOF	splash10-0059-0940000000-bbc0013de532edede483	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 90V, Negative-QTOF	splash10-004i-9100000000-d5a5ecd4f3c706f53a0f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 45V, Positive-QTOF	splash10-00kb-0910000000-a2eba6e125597cb7530d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 60V, Negative-QTOF	splash10-00b9-2900000000-1d8439ed7614ed714822	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 75V, Negative-QTOF	splash10-004i-9800000000-3f611dc53f826ce06536	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 10V, Positive-QTOF	splash10-03fr-0790000000-972234c38f1e6baf9909	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 20V, Positive-QTOF	splash10-03di-4930000000-1ab987bce4973d4f07f4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 40V, Positive-QTOF	splash10-0a4l-9500000000-53028683cce560c7a65b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 10V, Negative-QTOF	splash10-004i-0490000000-44a004dad8099c4e00de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 20V, Negative-QTOF	splash10-00w9-1940000000-8169435369a241584a63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 40V, Negative-QTOF	splash10-00fr-6900000000-56a7cc157be52d6494f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 10V, Positive-QTOF	splash10-004i-0290000000-bf11acdb8d5f1fa06aa5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 20V, Positive-QTOF	splash10-0532-2940000000-474dfefcab564610df5f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 40V, Positive-QTOF	splash10-0a4i-9500000000-0b315e8ad86892867d12	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 10V, Negative-QTOF	splash10-004i-0290000000-048ea11376b7fe328007	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 20V, Negative-QTOF	splash10-00b9-5950000000-012e94386a547e3c0c23	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethylhexyl phthalic acid 40V, Negative-QTOF	splash10-004i-9410000000-a8dbecb62f34e602da89	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Sweat
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 but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.00109 (0.000971-0.00123) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.000865 (0.000772-0.000975) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Sweat	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	screen-positive CF	Adriana Nori...	details

Associated Disorders and Diseases

Disease References

Cystic fibrosis
Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]

Associated OMIM IDs

219700 (Cystic fibrosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029358

KNApSAcK ID

Not Available

Chemspider ID

19208

KEGG Compound ID

C03343

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20393

PDB ID

Not Available

ChEBI ID

17243

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

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Hasmall SC, James NH, Macdonald N, West D, Chevalier S, Cosulich SC, Roberts RA: Suppression of apoptosis and induction of DNA synthesis in vitro by the phthalate plasticizers monoethylhexylphthalate (MEHP) and diisononylphthalate (DINP): a comparison of rat and human hepatocytes in vitro. Arch Toxicol. 1999 Nov;73(8-9):451-6. [PubMed:10650916 ]
Anderson WA, Barnes KA, Castle L, Damant AP, Scotter MJ: Determination of isotopically labelled monoesterphthalates in urine by high performance liquid chromatography-mass spectrometry. Analyst. 2002 Sep;127(9):1193-7. [PubMed:12375842 ]
Marttinen SK, Kettunen RH, Sormunen KM, Rintala JA: Removal of bis(2-ethylhexyl) phthalate at a sewage treatment plant. Water Res. 2003 Mar;37(6):1385-93. [PubMed:12598201 ]
Quintana JB, Rodil R, Reemtsma T: Determination of phosphoric acid mono- and diesters in municipal wastewater by solid-phase extraction and ion-pair liquid chromatography-tandem mass spectrometry. Anal Chem. 2006 Mar 1;78(5):1644-50. [PubMed:16503618 ]
Luisi S, Latini G, de Felice C, Sanseverino F, di Pasquale D, Mazzeo P, Petraglia F: Low serum concentrations of di-(2-ethylhexyl)phthalate in women with uterine fibromatosis. Gynecol Endocrinol. 2006 Feb;22(2):92-5. [PubMed:16603434 ]
Howdeshell KL, Furr J, Lambright CR, Rider CV, Wilson VS, Gray LE Jr: Cumulative effects of dibutyl phthalate and diethylhexyl phthalate on male rat reproductive tract development: altered fetal steroid hormones and genes. Toxicol Sci. 2007 Sep;99(1):190-202. Epub 2007 Mar 30. [PubMed:17400582 ]
Lovekamp-Swan T, Davis BJ: Mechanisms of phthalate ester toxicity in the female reproductive system. Environ Health Perspect. 2003 Feb;111(2):139-45. [PubMed:12573895 ]
Kambia K, Dine T, Gressier B, Dupin-Spriet T, Luyckx M, Brunet C: Evaluation of the direct toxicity of trioctyltrimellitate (TOTM), di(2-ethylhexyl) phthalate (DEHP) and their hydrolysis products on isolated rat hepatocytes. Int J Artif Organs. 2004 Nov;27(11):971-8. [PubMed:15636055 ]
Rosado-Berrios CA, Velez C, Zayas B: Mitochondrial permeability and toxicity of diethylhexyl and monoethylhexyl phthalates on TK6 human lymphoblasts cells. Toxicol In Vitro. 2011 Dec;25(8):2010-6. doi: 10.1016/j.tiv.2011.08.001. Epub 2011 Aug 16. [PubMed:21864672 ]
Rokos CL, Ledwith BJ: Peroxisome proliferators activate extracellular signal-regulated kinases in immortalized mouse liver cells. J Biol Chem. 1997 May 16;272(20):13452-7. [PubMed:9148971 ]
Forgacs AL, Ding Q, Jaremba RG, Huhtaniemi IT, Rahman NA, Zacharewski TR: BLTK1 murine Leydig cells: a novel steroidogenic model for evaluating the effects of reproductive and developmental toxicants. Toxicol Sci. 2012 Jun;127(2):391-402. doi: 10.1093/toxsci/kfs121. Epub 2012 Mar 29. [PubMed:22461451 ]
Janer G, Verhoef A, Gilsing HD, Piersma AH: Use of the rat postimplantation embryo culture to assess the embryotoxic potency within a chemical category and to identify toxic metabolites. Toxicol In Vitro. 2008 Oct;22(7):1797-805. doi: 10.1016/j.tiv.2008.07.007. Epub 2008 Jul 15. [PubMed:18675337 ]
Theunissen PT, Robinson JF, Pennings JL, van Herwijnen MH, Kleinjans JC, Piersma AH: Compound-specific effects of diverse neurodevelopmental toxicants on global gene expression in the neural embryonic stem cell test (ESTn). Toxicol Appl Pharmacol. 2012 Aug 1;262(3):330-40. doi: 10.1016/j.taap.2012.05.011. Epub 2012 May 23. [PubMed:22634333 ]
Hoppin JA, Brock JW, Davis BJ, Baird DD: Reproducibility of urinary phthalate metabolites in first morning urine samples. Environ Health Perspect. 2002 May;110(5):515-8. [PubMed:12003755 ]
Kato K, Shoda S, Takahashi M, Doi N, Yoshimura Y, Nakazawa H: Determination of three phthalate metabolites in human urine using on-line solid-phase extraction-liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 May 25;788(2):407-11. [PubMed:12705982 ]
Koo HJ, Lee BM: Human monitoring of phthalates and risk assessment. J Toxicol Environ Health A. 2005 Aug 27;68(16):1379-92. [PubMed:16009652 ]
Kim SH, Chun S, Jang JY, Chae HD, Kim CH, Kang BM: Increased plasma levels of phthalate esters in women with advanced-stage endometriosis: a prospective case-control study. Fertil Steril. 2011 Jan;95(1):357-9. doi: 10.1016/j.fertnstert.2010.07.1059. Epub 2010 Aug 25. [PubMed:20797718 ]
Ge RS, Chen GR, Dong Q, Akingbemi B, Sottas CM, Santos M, Sealfon SC, Bernard DJ, Hardy MP: Biphasic effects of postnatal exposure to diethylhexylphthalate on the timing of puberty in male rats. J Androl. 2007 Jul-Aug;28(4):513-20. Epub 2007 Feb 7. [PubMed:17287459 ]
Hoppin JA, Ulmer R, London SJ: Phthalate exposure and pulmonary function. Environ Health Perspect. 2004 Apr;112(5):571-4. [PubMed:15064163 ]
Barron MG, Schultz IR, Hayton WL: Presystemic branchial metabolism limits di-2-ethylhexyl phthalate accumulation in fish. Toxicol Appl Pharmacol. 1989 Mar 15;98(1):49-57. [PubMed:2929021 ]
Holm A, Solbu K, Molander P, Lundanes E, Greibrokk T: Sensitive biomonitoring of phthalate metabolites in human urine using packed capillary column switching liquid chromatography coupled to electrospray ionization ion-trap mass spectrometry. Anal Bioanal Chem. 2004 Apr;378(7):1762-8. Epub 2004 Jan 31. [PubMed:14758462 ]
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Ellero-Simatos S, Claus SP, Benelli C, Forest C, Letourneur F, Cagnard N, Beaune PH, de Waziers I: Combined transcriptomic-(1)H NMR metabonomic study reveals that monoethylhexyl phthalate stimulates adipogenesis and glyceroneogenesis in human adipocytes. J Proteome Res. 2011 Dec 2;10(12):5493-502. doi: 10.1021/pr200765v. Epub 2011 Nov 9. [PubMed:22017230 ]
Rose ML, Rivera CA, Bradford BU, Graves LM, Cattley RC, Schoonhoven R, Swenberg JA, Thurman RG: Kupffer cell oxidant production is central to the mechanism of peroxisome proliferators. Carcinogenesis. 1999 Jan;20(1):27-33. [PubMed:9934846 ]

Showing metabocard for Monoethylhexyl phthalic acid (HMDB0013248)

MOL for HMDB0013248 (Monoethylhexyl phthalic acid)

3D MOL for HMDB0013248 (Monoethylhexyl phthalic acid)

3D SDF for HMDB0013248 (Monoethylhexyl phthalic acid)

3D-SDF for HMDB0013248 (Monoethylhexyl phthalic acid)

PDB for HMDB0013248 (Monoethylhexyl phthalic acid)

3D PDB for HMDB0013248 (Monoethylhexyl phthalic acid)

SMILES for HMDB0013248 (Monoethylhexyl phthalic acid)

INCHI for HMDB0013248 (Monoethylhexyl phthalic acid)

Structure for HMDB0013248 (Monoethylhexyl phthalic acid)

3D Structure for HMDB0013248 (Monoethylhexyl phthalic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra