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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2017-08-01 02:12:04 UTC

Update Date

2021-09-14 15:44:55 UTC

HMDB ID

HMDB0094647

Secondary Accession Numbers

HMDB94647

Metabolite Identification

Common Name

Mono-(2-ethyl-5-carboxypentyl) phthalate

Description

Mono-(2-ethyl-5-carboxypentyl) phthalate is also known as 2-ethyl-5-carboxypentyl phthalate, MECPP or phthalate, mono(5-carboxy-2-ethylpentyl) ester. It is classified as a member of the benzoic acid esters. Benzoic acid esters are ester derivatives of benzoic acid. Mono-(2-ethyl-5-carboxypentyl) phthalate is considered to be practically insoluble (in water) and acidic. (ChemoSummarizer). It is a metabolite of mono(2-ethylhexyl) phthalate (MEHP) and a secondary metabolite of di(2-ethylhexyl) phthalate (DEHP).

Structure

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

HMDB0094647
     RDKit          3D
Mono-(2-ethyl-5-carboxypentyl) phthalate
 42 42  0  0  0  0  0  0  0  0999 V2000
   -1.1200    3.0490    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0342    2.2865   -0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249    0.8267   -0.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8613    0.6839   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2172   -0.7756   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6360   -1.0452    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9403   -0.5477    1.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0911   -0.0252    2.1752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2443   -0.6537    1.9496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252    0.0330    0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401    0.0794   -0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8470   -0.6356    0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831   -1.2205    1.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2096   -0.5867   -0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853    0.1570   -1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7488    0.2426   -1.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8197   -0.3947   -1.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5603   -1.1181   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -1.2237    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -2.0193    1.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715   -2.5769    1.9982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947   -2.2669    2.2291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9303    2.8029    0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511    3.0619    0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2690    4.1371    0.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903    2.7359   -1.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0023    2.3161   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3945    0.4303   -1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5348    1.2174   -1.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330    1.1467    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -1.3088    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -1.3140   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8451   -2.1401    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477   -0.5735   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9019   -1.3321    1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5826    0.3073    1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7374   -1.0683   -0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585    0.6638   -1.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9443    0.8268   -2.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8113   -0.3031   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3746   -1.6283    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9157   -2.2462    3.2539 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
  7  8  2  0
  7  9  1  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 22 42  1  0
M  END


  Mrv0541 09111411542D          

 22 22  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    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
    0.0000    2.4750    0.0000 O   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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  2  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18 14  1  0  0  0  0
 19 15  2  0  0  0  0
 20 15  1  0  0  0  0
 21 16  2  0  0  0  0
 22 10  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0094647

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(CCCC(O)=O)COC(=O)C1=CC=CC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O6/c1-2-11(6-5-9-14(17)18)10-22-16(21)13-8-4-3-7-12(13)15(19)20/h3-4,7-8,11H,2,5-6,9-10H2,1H3,(H,17,18)(H,19,20)

> <INCHI_KEY>
XFGRNAPKLGXDGF-UHFFFAOYSA-N

> <FORMULA>
C16H20O6

> <MOLECULAR_WEIGHT>
308.3264

> <EXACT_MASS>
308.125988372

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.23797616496342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[(5-carboxy-2-ethylpentyl)oxy]carbonyl}benzoic acid

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
3.336641759

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.137745226914414

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0273448189258314

> <JCHEM_PKA_STRONGEST_BASIC>
-6.956960801852763

> <JCHEM_POLAR_SURFACE_AREA>
100.89999999999999

> <JCHEM_REFRACTIVITY>
79.15309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(5-carboxy-2-ethylpentyl)oxy]carbonyl}benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0094647
     RDKit          3D
Mono-(2-ethyl-5-carboxypentyl) phthalate
 42 42  0  0  0  0  0  0  0  0999 V2000
   -1.1200    3.0490    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0342    2.2865   -0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249    0.8267   -0.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8613    0.6839   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2172   -0.7756   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6360   -1.0452    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9403   -0.5477    1.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0911   -0.0252    2.1752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2443   -0.6537    1.9496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252    0.0330    0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401    0.0794   -0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8470   -0.6356    0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831   -1.2205    1.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2096   -0.5867   -0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853    0.1570   -1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7488    0.2426   -1.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8197   -0.3947   -1.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5603   -1.1181   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -1.2237    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -2.0193    1.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715   -2.5769    1.9982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947   -2.2669    2.2291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9303    2.8029    0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511    3.0619    0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2690    4.1371    0.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903    2.7359   -1.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0023    2.3161   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3945    0.4303   -1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5348    1.2174   -1.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330    1.1467    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -1.3088    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -1.3140   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8451   -2.1401    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477   -0.5735   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9019   -1.3321    1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5826    0.3073    1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7374   -1.0683   -0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585    0.6638   -1.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9443    0.8268   -2.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8113   -0.3031   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3746   -1.6283    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9157   -2.2462    3.2539 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
  7  8  2  0
  7  9  1  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 22 42  1  0
M  END

HEADER    PROTEIN                                 11-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-14         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.670   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   11                                                       
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   11                                                       
CONECT    7    3   12                                                       
CONECT    8    4   13                                                       
CONECT    9    5   14                                                       
CONECT   10   11   22                                                       
CONECT   11    2    6   10                                                  
CONECT   12    7   13   15                                                  
CONECT   13    8   12   16                                                  
CONECT   14    9   17   18                                                  
CONECT   15   12   19   20                                                  
CONECT   16   13   21   22                                                  
CONECT   17   14                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0094647
HETATM    1  C1  UNL     1      -1.120   3.049   0.313  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.034   2.287  -0.950  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.425   0.827  -0.856  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.861   0.684  -0.391  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.217  -0.776  -0.313  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.636  -1.045   0.100  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.940  -0.548   1.443  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.091  -0.025   2.175  1.00  0.00           O  
HETATM    9  O2  UNL     1      -6.244  -0.654   1.950  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.525   0.033   0.003  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.840   0.079  -0.484  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.847  -0.636   0.231  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.383  -1.221   1.212  1.00  0.00           O  
HETATM   14  C10 UNL     1       3.210  -0.587  -0.259  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.485   0.157  -1.414  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.749   0.243  -1.928  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.820  -0.395  -1.342  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.560  -1.118  -0.221  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.254  -1.224   0.335  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.114  -2.019   1.524  1.00  0.00           C  
HETATM   21  O5  UNL     1       5.171  -2.577   1.998  1.00  0.00           O  
HETATM   22  O6  UNL     1       2.995  -2.267   2.229  1.00  0.00           O  
HETATM   23  H1  UNL     1      -1.930   2.803   0.996  1.00  0.00           H  
HETATM   24  H2  UNL     1      -0.151   3.062   0.894  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.269   4.137   0.042  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.690   2.736  -1.729  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.002   2.316  -1.333  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.394   0.430  -1.893  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.535   1.217  -1.115  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.033   1.147   0.580  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.587  -1.309   0.461  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.030  -1.314  -1.261  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.845  -2.140   0.047  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.348  -0.574  -0.630  1.00  0.00           H  
HETATM   35  H13 UNL     1      -6.902  -1.332   1.545  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.583   0.307   1.073  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.737  -1.068  -0.046  1.00  0.00           H  
HETATM   38  H16 UNL     1       2.658   0.664  -1.887  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.944   0.827  -2.830  1.00  0.00           H  
HETATM   40  H18 UNL     1       6.811  -0.303  -1.781  1.00  0.00           H  
HETATM   41  H19 UNL     1       6.375  -1.628   0.261  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.916  -2.246   3.254  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   10   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8    8    9
CONECT    9   35
CONECT   10   11   36   37
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   19
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   42
END

HMDB0094647
     RDKit          3D
Mono-(2-ethyl-5-carboxypentyl) phthalate
 42 42  0  0  0  0  0  0  0  0999 V2000
   -1.1200    3.0490    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0342    2.2865   -0.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249    0.8267   -0.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8613    0.6839   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2172   -0.7756   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6360   -1.0452    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9403   -0.5477    1.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0911   -0.0252    2.1752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2443   -0.6537    1.9496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5252    0.0330    0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401    0.0794   -0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8470   -0.6356    0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831   -1.2205    1.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2096   -0.5867   -0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853    0.1570   -1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7488    0.2426   -1.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8197   -0.3947   -1.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5603   -1.1181   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -1.2237    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -2.0193    1.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715   -2.5769    1.9982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947   -2.2669    2.2291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9303    2.8029    0.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511    3.0619    0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2690    4.1371    0.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903    2.7359   -1.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0023    2.3161   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3945    0.4303   -1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5348    1.2174   -1.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330    1.1467    0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -1.3088    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304   -1.3140   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8451   -2.1401    0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477   -0.5735   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9019   -1.3321    1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5826    0.3073    1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7374   -1.0683   -0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585    0.6638   -1.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9443    0.8268   -2.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8113   -0.3031   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3746   -1.6283    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9157   -2.2462    3.2539 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
  7  8  2  0
  7  9  1  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 22 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Benzenedicarboxylic acid, mono(5-carboxy-2-ethylpentyl) ester	ChEBI
2-Ethyl-5-carboxypentyl phthalate	ChEBI
MECPP	ChEBI
Phthalic acid, mono(5-carboxy-2-ethylpentyl) ester	ChEBI
1,2-Benzenedicarboxylate, mono(5-carboxy-2-ethylpentyl) ester	Generator
2-Ethyl-5-carboxypentyl phthalic acid	Generator
Phthalate, mono(5-carboxy-2-ethylpentyl) ester	Generator
mono-(2-Ethyl-5-carboxypentyl) phthalic acid	Generator
mono(5-Carboxy-2-ethylpentyl) phthalic acid	HMDB

Chemical Formula

C₁₆H₂₀O₆

Average Molecular Weight

308.3264

Monoisotopic Molecular Weight

308.125988372

IUPAC Name

2-{[(5-carboxy-2-ethylpentyl)oxy]carbonyl}benzoic acid

Traditional Name

2-{[(5-carboxy-2-ethylpentyl)oxy]carbonyl}benzoic acid

CAS Registry Number

Not Available

SMILES

CCC(CCCC(O)=O)COC(=O)C1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C16H20O6/c1-2-11(6-5-9-14(17)18)10-22-16(21)13-8-4-3-7-12(13)15(19)20/h3-4,7-8,11H,2,5-6,9-10H2,1H3,(H,17,18)(H,19,20)

InChI Key

XFGRNAPKLGXDGF-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
Tricarboxylic acid or derivatives
Benzoic acid
Benzoyl
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (HMDB: HMDB0094647)

Cellular substructure

Membrane (HMDB: HMDB0094647)
Microsome (HMDB: HMDB0094647)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Mono-(2-ethyl-5-carboxypentyl) phthalate Exposure (MarkerDB: MDB00029807)

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	2.52	ALOGPS
logP	3.34	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.03	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	79.15 m³·mol⁻¹	ChemAxon
Polarizability	32.24 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]+	173.137	31661259
DarkChem	[M-H]-	168.527	31661259
DeepCCS	[M+H]+	175.683	30932474
DeepCCS	[M-H]-	173.325	30932474
DeepCCS	[M-2H]-	206.211	30932474
DeepCCS	[M+Na]+	181.776	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.6	32859911
AllCCS	[M+NH4]+	174.4	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	172.3	32859911
AllCCS	[M+Na-2H]-	172.6	32859911
AllCCS	[M+HCOO]-	173.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mono-(2-ethyl-5-carboxypentyl) phthalate	CCC(CCCC(O)=O)COC(=O)C1=CC=CC=C1C(O)=O	3803.5	Standard polar	33892256
Mono-(2-ethyl-5-carboxypentyl) phthalate	CCC(CCCC(O)=O)COC(=O)C1=CC=CC=C1C(O)=O	2152.8	Standard non polar	33892256
Mono-(2-ethyl-5-carboxypentyl) phthalate	CCC(CCCC(O)=O)COC(=O)C1=CC=CC=C1C(O)=O	2512.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mono-(2-ethyl-5-carboxypentyl) phthalate,1TMS,isomer #1	CCC(CCCC(=O)O[Si](C)(C)C)COC(=O)C1=CC=CC=C1C(=O)O	2525.8	Semi standard non polar	33892256
Mono-(2-ethyl-5-carboxypentyl) phthalate,1TMS,isomer #2	CCC(CCCC(=O)O)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C	2537.5	Semi standard non polar	33892256
Mono-(2-ethyl-5-carboxypentyl) phthalate,2TMS,isomer #1	CCC(CCCC(=O)O[Si](C)(C)C)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C	2525.6	Semi standard non polar	33892256
Mono-(2-ethyl-5-carboxypentyl) phthalate,1TBDMS,isomer #1	CCC(CCCC(=O)O[Si](C)(C)C(C)(C)C)COC(=O)C1=CC=CC=C1C(=O)O	2764.1	Semi standard non polar	33892256
Mono-(2-ethyl-5-carboxypentyl) phthalate,1TBDMS,isomer #2	CCC(CCCC(=O)O)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2757.9	Semi standard non polar	33892256
Mono-(2-ethyl-5-carboxypentyl) phthalate,2TBDMS,isomer #1	CCC(CCCC(=O)O[Si](C)(C)C(C)(C)C)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2975.6	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-(2-ethyl-5-carboxypentyl) phthalate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-5930000000-197ddba064e06789267b	2017-09-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6193200000-77ca54dc43f7b87574e3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 10V, Positive-QTOF	splash10-052g-0693000000-d967e1f8272f0f805b59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 20V, Positive-QTOF	splash10-0005-5890000000-c57911b38ab12f8775e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 40V, Positive-QTOF	splash10-052b-9610000000-8c6d47554900383920b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 10V, Negative-QTOF	splash10-0bt9-0669000000-08bcf24c2001ef7fa6a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 20V, Negative-QTOF	splash10-0829-1951000000-7e48dff5ec566e7669e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 40V, Negative-QTOF	splash10-0600-5910000000-50ddb5302385aa1287dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 10V, Negative-QTOF	splash10-0ab9-2946000000-2de500123a8003033b7d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 20V, Negative-QTOF	splash10-06fr-6960000000-f5d722b22908b8f646f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 40V, Negative-QTOF	splash10-004i-9300000000-bec66037feb53a82d8d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 10V, Positive-QTOF	splash10-052e-0592000000-377839f443ddee280aa9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 20V, Positive-QTOF	splash10-0002-0930000000-1a8fb1d10c3775601130	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-carboxypentyl) phthalate 40V, Positive-QTOF	splash10-0537-9800000000-c9b899e65fc2904e9535	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.00752 (0.00656-0.00862) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.0132 (0.0119-0.0148) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	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

148386

PDB ID

Not Available

ChEBI ID

132611

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029807

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hauser R, Gaskins AJ, Souter I, Smith KW, Dodge LE, Ehrlich S, Meeker JD, Calafat AM, Williams PL: Urinary Phthalate Metabolite Concentrations and Reproductive Outcomes among Women Undergoing in Vitro Fertilization: Results from the EARTH Study. Environ Health Perspect. 2016 Jun;124(6):831-9. doi: 10.1289/ehp.1509760. Epub 2015 Nov 6. [PubMed:26545148 ]
Leuenberger N, Barras L, Nicoli R, Robinson N, Baume N, Lion N, Barelli S, Tissot JD, Saugy M: Urinary di-(2-ethylhexyl) phthalate metabolites for detecting transfusion of autologous blood stored in plasticizer-free bags. Transfusion. 2016 Mar;56(3):571-8. doi: 10.1111/trf.13408. Epub 2015 Nov 18. [PubMed:26581034 ]

Showing metabocard for Mono-(2-ethyl-5-carboxypentyl) phthalate (HMDB0094647)

MOL for HMDB0094647 (Mono-(2-ethyl-5-carboxypentyl) phthalate)

3D MOL for HMDB0094647 (Mono-(2-ethyl-5-carboxypentyl) phthalate)

3D SDF for HMDB0094647 (Mono-(2-ethyl-5-carboxypentyl) phthalate)

3D-SDF for HMDB0094647 (Mono-(2-ethyl-5-carboxypentyl) phthalate)

PDB for HMDB0094647 (Mono-(2-ethyl-5-carboxypentyl) phthalate)

3D PDB for HMDB0094647 (Mono-(2-ethyl-5-carboxypentyl) phthalate)

SMILES for HMDB0094647 (Mono-(2-ethyl-5-carboxypentyl) phthalate)

INCHI for HMDB0094647 (Mono-(2-ethyl-5-carboxypentyl) phthalate)

Structure for HMDB0094647 (Mono-(2-ethyl-5-carboxypentyl) phthalate)

3D Structure for HMDB0094647 (Mono-(2-ethyl-5-carboxypentyl) phthalate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra