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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2017-08-01 02:16:41 UTC

Update Date

2021-09-14 15:45:00 UTC

HMDB ID

HMDB0094679

Secondary Accession Numbers

HMDB94679

Metabolite Identification

Common Name

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

Description

Mono-(2-ethyl-5-hydroxyhexyl) phthalate, also known as 40321-99-1 or phthalic acid mono(2-ethyl-5-hydroxyhexyl) ester, is classified as a member of the benzoic acid esters. Benzoic acid esters are ester derivatives of benzoic acid. 40321-99-1 is considered to be practically insoluble (in water) and acidic. (ChemoSummarizer) Mono-(2-ethyl-5-hydroxyhexyl) phthalate is a metabolite of mono(2-ethylhexyl) phthalate (MEHP) and a secondary metabolite of di(2-ethylhexyl) phthalate (DEHP) [Exposome-Explorer]. Di(2-ethylhexyl) phthalate (DEHP) is added to polyvinyl chloride (PVC) plastics used widely in medical devices and toys to impart flexibility and durability (Pubmed: 16332407).

Structure

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

HMDB0094679
     RDKit          3D
Mono-(2-ethyl-5-hydroxyhexyl) phthalate
 43 43  0  0  0  0  0  0  0  0999 V2000
   -2.7781   -1.9874    1.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375   -0.5837    1.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2102   -0.0655    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023   -0.0086   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280    0.7897   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6760    0.7408   -1.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627   -0.5259   -1.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765    1.3621   -0.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835   -0.9807    1.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644   -0.6858    0.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    0.4372    0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2966    1.3451    1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2203    0.7754    0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431    2.0581    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9669    2.4666    0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7455    1.6324   -0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2680    0.3902   -0.7559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0012   -0.0337   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933   -1.3758   -0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4098   -2.0810   -1.3918 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -2.0205   -0.3568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1683   -2.7534    1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6610   -2.1590    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8692   -2.1263    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768    0.0798    1.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937   -0.7485    2.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9525    0.9276    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291    0.3028   -0.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009   -1.0686   -0.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9163    1.8951   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9171    0.7176   -2.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0321    1.4538   -2.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2809   -0.3063   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7782   -1.0440   -0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730   -1.2301   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6967    2.1252    0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -0.9607    2.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3293   -2.0421    1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1394    2.7228    1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3457    3.4684    0.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7237    1.9071   -0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806   -0.2817   -1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363   -2.5284   -1.0747 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
  6  8  1  0
  3  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 21 43  1  0
M  END

  Mrv1572003201609422D          

 21 21  0  0  0  0            999 V2000
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  3  9  1  0  0  0  0
  9 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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0094679

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O5/c1-3-12(9-8-11(2)17)10-21-16(20)14-7-5-4-6-13(14)15(18)19/h4-7,11-12,17H,3,8-10H2,1-2H3,(H,18,19)

> <INCHI_KEY>
RYPQSGURZSTFSX-UHFFFAOYSA-N

> <FORMULA>
C16H22O5

> <MOLECULAR_WEIGHT>
294.347

> <EXACT_MASS>
294.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.428386976334856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.1922112670000007

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.608976169819442

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.084683642302213

> <JCHEM_PKA_STRONGEST_BASIC>
-1.657639504195338

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
79.2342

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0094679
     RDKit          3D
Mono-(2-ethyl-5-hydroxyhexyl) phthalate
 43 43  0  0  0  0  0  0  0  0999 V2000
   -2.7781   -1.9874    1.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375   -0.5837    1.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2102   -0.0655    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023   -0.0086   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280    0.7897   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6760    0.7408   -1.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627   -0.5259   -1.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765    1.3621   -0.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835   -0.9807    1.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644   -0.6858    0.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    0.4372    0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2966    1.3451    1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2203    0.7754    0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431    2.0581    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9669    2.4666    0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7455    1.6324   -0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2680    0.3902   -0.7559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0012   -0.0337   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933   -1.3758   -0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4098   -2.0810   -1.3918 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -2.0205   -0.3568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1683   -2.7534    1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6610   -2.1590    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8692   -2.1263    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768    0.0798    1.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937   -0.7485    2.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9525    0.9276    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291    0.3028   -0.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009   -1.0686   -0.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9163    1.8951   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9171    0.7176   -2.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0321    1.4538   -2.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2809   -0.3063   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7782   -1.0440   -0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730   -1.2301   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6967    2.1252    0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -0.9607    2.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3293   -2.0421    1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1394    2.7228    1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3457    3.4684    0.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7237    1.9071   -0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806   -0.2817   -1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363   -2.5284   -1.0747 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
  6  8  1  0
  3  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 21 43  1  0
M  END

HEADER    PROTEIN                                 20-MAR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-16         0                                  
HETATM    1  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.337 -13.860   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0094679
HETATM    1  C1  UNL     1      -2.778  -1.987   1.114  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.437  -0.584   1.575  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.210  -0.066   0.897  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.302  -0.009  -0.564  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.228   0.790  -1.320  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.676   0.741  -1.303  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.363  -0.526  -1.633  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.277   1.362  -0.230  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.084  -0.981   1.383  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.164  -0.686   0.875  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.917   0.437   0.978  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.297   1.345   1.690  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.220   0.775   0.459  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.743   2.058   0.749  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.967   2.467   0.301  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.746   1.632  -0.460  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.268   0.390  -0.756  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.001  -0.034  -0.293  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.593  -1.376  -0.668  1.00  0.00           C  
HETATM   20  O4  UNL     1       4.410  -2.081  -1.392  1.00  0.00           O  
HETATM   21  O5  UNL     1       2.436  -2.021  -0.357  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.168  -2.753   1.643  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.661  -2.159   0.049  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.869  -2.126   1.354  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.277   0.080   1.688  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.094  -0.749   2.670  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.952   0.928   1.365  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.229   0.303  -0.895  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.301  -1.069  -0.999  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.916   1.895  -1.147  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.917   0.718  -2.436  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.032   1.454  -2.183  1.00  0.00           H  
HETATM   33  H12 UNL     1      -5.281  -0.306  -2.217  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.778  -1.044  -0.719  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.773  -1.230  -2.249  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.697   2.125   0.050  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.158  -0.961   2.492  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.329  -2.042   1.092  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.139   2.723   1.347  1.00  0.00           H  
HETATM   40  H19 UNL     1       5.346   3.468   0.543  1.00  0.00           H  
HETATM   41  H20 UNL     1       6.724   1.907  -0.840  1.00  0.00           H  
HETATM   42  H21 UNL     1       5.881  -0.282  -1.361  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.936  -2.528  -1.075  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4    9   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7    8   32
CONECT    7   33   34   35
CONECT    8   36
CONECT    9   10   37   38
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   14   18
CONECT   14   15   39
CONECT   15   16   16   40
CONECT   16   17   41
CONECT   17   18   18   42
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   43
END

HMDB0094679
     RDKit          3D
Mono-(2-ethyl-5-hydroxyhexyl) phthalate
 43 43  0  0  0  0  0  0  0  0999 V2000
   -2.7781   -1.9874    1.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375   -0.5837    1.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2102   -0.0655    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023   -0.0086   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280    0.7897   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6760    0.7408   -1.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627   -0.5259   -1.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765    1.3621   -0.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835   -0.9807    1.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644   -0.6858    0.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    0.4372    0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2966    1.3451    1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2203    0.7754    0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7431    2.0581    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9669    2.4666    0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7455    1.6324   -0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2680    0.3902   -0.7559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0012   -0.0337   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933   -1.3758   -0.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4098   -2.0810   -1.3918 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -2.0205   -0.3568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1683   -2.7534    1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6610   -2.1590    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8692   -2.1263    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768    0.0798    1.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937   -0.7485    2.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9525    0.9276    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291    0.3028   -0.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009   -1.0686   -0.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9163    1.8951   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9171    0.7176   -2.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0321    1.4538   -2.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2809   -0.3063   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7782   -1.0440   -0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730   -1.2301   -2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6967    2.1252    0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -0.9607    2.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3293   -2.0421    1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1394    2.7228    1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3457    3.4684    0.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7237    1.9071   -0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806   -0.2817   -1.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363   -2.5284   -1.0747 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
  6  8  1  0
  3  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Benzenedicarboxylic acid, mono(2-ethyl-5-hydroxyhexyl) ester	ChEBI
mono(2-Ethyl-5-hydroxyhexyl) 1,2-benzenedicarboxylate	ChEBI
Phthalic acid mono(2-ethyl-5-hydroxyhexyl) ester	ChEBI
1,2-Benzenedicarboxylate, mono(2-ethyl-5-hydroxyhexyl) ester	Generator
mono(2-Ethyl-5-hydroxyhexyl) 1,2-benzenedicarboxylic acid	Generator
Phthalate mono(2-ethyl-5-hydroxyhexyl) ester	Generator
mono(2-Ethyl-5-hydroxyhexyl) phthalic acid	Generator
mono(2-Ethyl-5-hydroxyhexyl)phthalate	MeSH, HMDB
MEHHP CPD	MeSH, HMDB
mono(2-Ethyl-5-hydroxyhexyl) phthalate	MeSH, HMDB
mono-(2-Ethyl-5-hydroxyhexyl) phthalic acid	Generator

Chemical Formula

C₁₆H₂₂O₅

Average Molecular Weight

294.347

Monoisotopic Molecular Weight

294.146723808

IUPAC Name

2-{[(2-ethyl-5-hydroxyhexyl)oxy]carbonyl}benzoic acid

Traditional Name

2-{[(2-ethyl-5-hydroxyhexyl)oxy]carbonyl}benzoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H22O5/c1-3-12(9-8-11(2)17)10-21-16(20)14-7-5-4-6-13(14)15(18)19/h4-7,11-12,17H,3,8-10H2,1-2H3,(H,18,19)

InChI Key

RYPQSGURZSTFSX-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
Fatty alcohol
Benzoyl
Dicarboxylic acid or derivatives
Fatty acyl
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (HMDB: HMDB0094679)

Cellular substructure

Membrane (HMDB: HMDB0094679)

Organelle

Peroxisome (HMDB: HMDB0094679)

Source

Exogenous

Exogenous (HMDB: HMDB0094679)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0094679)

Role

Industrial application

Pharmaceutical industry

Biomarker

Mono-(2-ethyl-5-hydroxyhexyl) phthalate Exposure (MarkerDB: MDB00029808)

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	2.69	ALOGPS
logP	3.19	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	79.23 m³·mol⁻¹	ChemAxon
Polarizability	31.43 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]+	170.132	31661259
DarkChem	[M-H]-	167.609	31661259
DeepCCS	[M+H]+	172.153	30932474
DeepCCS	[M-H]-	169.795	30932474
DeepCCS	[M-2H]-	202.681	30932474
DeepCCS	[M+Na]+	178.246	30932474
AllCCS	[M+H]+	170.9	32859911
AllCCS	[M+H-H2O]+	167.7	32859911
AllCCS	[M+NH4]+	173.7	32859911
AllCCS	[M+Na]+	174.6	32859911
AllCCS	[M-H]-	170.9	32859911
AllCCS	[M+Na-2H]-	171.4	32859911
AllCCS	[M+HCOO]-	172.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mono-(2-ethyl-5-hydroxyhexyl) phthalate	CCC(CCC(C)O)COC(=O)C1=CC=CC=C1C(O)=O	3589.2	Standard polar	33892256
Mono-(2-ethyl-5-hydroxyhexyl) phthalate	CCC(CCC(C)O)COC(=O)C1=CC=CC=C1C(O)=O	2133.6	Standard non polar	33892256
Mono-(2-ethyl-5-hydroxyhexyl) phthalate	CCC(CCC(C)O)COC(=O)C1=CC=CC=C1C(O)=O	2345.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mono-(2-ethyl-5-hydroxyhexyl) phthalate,1TMS,isomer #1	CCC(CCC(C)O[Si](C)(C)C)COC(=O)C1=CC=CC=C1C(=O)O	2360.3	Semi standard non polar	33892256
Mono-(2-ethyl-5-hydroxyhexyl) phthalate,1TMS,isomer #2	CCC(CCC(C)O)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C	2342.1	Semi standard non polar	33892256
Mono-(2-ethyl-5-hydroxyhexyl) phthalate,2TMS,isomer #1	CCC(CCC(C)O[Si](C)(C)C)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C	2364.7	Semi standard non polar	33892256
Mono-(2-ethyl-5-hydroxyhexyl) phthalate,1TBDMS,isomer #1	CCC(CCC(C)O[Si](C)(C)C(C)(C)C)COC(=O)C1=CC=CC=C1C(=O)O	2583.6	Semi standard non polar	33892256
Mono-(2-ethyl-5-hydroxyhexyl) phthalate,1TBDMS,isomer #2	CCC(CCC(C)O)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2559.7	Semi standard non polar	33892256
Mono-(2-ethyl-5-hydroxyhexyl) phthalate,2TBDMS,isomer #1	CCC(CCC(C)O[Si](C)(C)C(C)(C)C)COC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2798.3	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-hydroxyhexyl) phthalate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-6920000000-b1a95205611c04a73fc0	2017-09-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6693200000-1a67c1275d85c6a44762	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) 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-hydroxyhexyl) phthalate 10V, Negative-QTOF	splash10-0006-0290000000-24e09fb0b84bded51d93	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate 20V, Negative-QTOF	splash10-01dm-1890000000-1ac217e7244be02c57a4	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate 40V, Negative-QTOF	splash10-0100-6900000000-c76fe25085b5d4b3ac8b	2017-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate 10V, Positive-QTOF	splash10-004j-0490000000-a9c9d893e8b8d475bcd8	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate 20V, Positive-QTOF	splash10-06vj-2970000000-482264ca5d84a0703abb	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate 40V, Positive-QTOF	splash10-0bu1-7930000000-5fdcd01906d07b642b35	2017-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate 10V, Negative-QTOF	splash10-0002-1940000000-d7eabd2ddaa7f3b9db62	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate 20V, Negative-QTOF	splash10-00b9-8910000000-95a9cd3c71e89eb5b230	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate 40V, Negative-QTOF	splash10-004i-9420000000-5e455a2b7471e1e83117	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate 10V, Positive-QTOF	splash10-004j-0290000000-8412a5dc1367cb9edf72	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate 20V, Positive-QTOF	splash10-0002-0950000000-d9fcf4ba5565be55732f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mono-(2-ethyl-5-hydroxyhexyl) phthalate 40V, Positive-QTOF	splash10-0a4i-2900000000-aaa86f10ae5ed769ad69	2021-09-24	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	0.00503 (0.00434-0.00584) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.00753 (0.00665-0.00853) 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

170295

PDB ID

Not Available

ChEBI ID

132607

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029808

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 ]
Wang YX, Zeng Q, Sun Y, Yang P, Wang P, Li J, Huang Z, You L, Huang YH, Wang C, Li YF, Lu WQ: Semen phthalate metabolites, semen quality parameters and serum reproductive hormones: A cross-sectional study in China. Environ Pollut. 2016 Apr;211:173-82. doi: 10.1016/j.envpol.2015.12.052. Epub 2016 Jan 14. [PubMed:26766535 ]
Alves A, Vanermen G, Covaci A, Voorspoels S: Ultrasound assisted extraction combined with dispersive liquid-liquid microextraction (US-DLLME)-a fast new approach to measure phthalate metabolites in nails. Anal Bioanal Chem. 2016 Sep;408(22):6169-80. doi: 10.1007/s00216-016-9727-1. Epub 2016 Jul 2. [PubMed:27372718 ]
Yao HY, Han Y, Gao H, Huang K, Ge X, Xu YY, Xu YQ, Jin ZX, Sheng J, Yan SQ, Zhu P, Hao JH, Tao FB: Maternal phthalate exposure during the first trimester and serum thyroid hormones in pregnant women and their newborns. Chemosphere. 2016 Aug;157:42-8. doi: 10.1016/j.chemosphere.2016.05.023. Epub 2016 May 18. [PubMed:27208644 ]

Showing metabocard for Mono-(2-ethyl-5-hydroxyhexyl) phthalate (HMDB0094679)

MOL for HMDB0094679 (Mono-(2-ethyl-5-hydroxyhexyl) phthalate)

3D MOL for HMDB0094679 (Mono-(2-ethyl-5-hydroxyhexyl) phthalate)

3D SDF for HMDB0094679 (Mono-(2-ethyl-5-hydroxyhexyl) phthalate)

3D-SDF for HMDB0094679 (Mono-(2-ethyl-5-hydroxyhexyl) phthalate)

PDB for HMDB0094679 (Mono-(2-ethyl-5-hydroxyhexyl) phthalate)

3D PDB for HMDB0094679 (Mono-(2-ethyl-5-hydroxyhexyl) phthalate)

SMILES for HMDB0094679 (Mono-(2-ethyl-5-hydroxyhexyl) phthalate)

INCHI for HMDB0094679 (Mono-(2-ethyl-5-hydroxyhexyl) phthalate)

Structure for HMDB0094679 (Mono-(2-ethyl-5-hydroxyhexyl) phthalate)

3D Structure for HMDB0094679 (Mono-(2-ethyl-5-hydroxyhexyl) phthalate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra