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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:18:17 UTC

Update Date

2022-03-07 02:54:07 UTC

HMDB ID

HMDB0034462

Secondary Accession Numbers

HMDB34462

Metabolite Identification

Common Name

Heptyl 4-hydroxybenzoate

Description

Heptyl 4-hydroxybenzoate, also known as heptylparaben or nipaheptyl, belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group. Heptyl 4-hydroxybenzoate is used as a food additive ("EAFUS: Everything Added to Food in the United States. "). Heptyl 4-hydroxybenzoate is a potentially toxic compound. No indication of carcinogenicity to humans (not listed by IARC). These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid. It is used as a food additive .

Structure

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

HMDB0034462
     RDKit          3D
Heptyl 4-hydroxybenzoate
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.2773    1.9632   -0.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5594    0.6898   -1.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2963   -0.1338   -1.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771   -0.4732   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107   -1.2991   -0.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0841   -1.5780    1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1755   -2.3996    1.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726   -1.7968    0.6921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8121   -0.5763    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561    0.0193    2.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9613    0.0188    0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6299   -0.5630   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7138    0.0052   -1.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487    1.2408   -0.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2501    1.8148   -1.4512 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5136    1.8638    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302    1.2418    0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376    2.5033   -1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680    1.7713    0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2116    2.5736   -0.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3324    0.1268   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0191    0.9384   -2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438   -1.0864   -2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352    0.3853   -2.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764    0.5036    0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5303   -0.9438    0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975   -0.7226   -0.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -2.2723   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -2.1754    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986   -0.6096    1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -3.3536    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3471   -2.6862    2.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2884   -1.5231   -1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2388   -0.4509   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911    2.4248   -2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8968    2.8170    0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9306    1.7419    1.6562 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  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END


  Mrv1652305271900152D          

 17 17  0  0  0  0            999 V2000
   -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
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    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    6.1875    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    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 11  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034462

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCOC(=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O3/c1-2-3-4-5-6-11-17-14(16)12-7-9-13(15)10-8-12/h7-10,15H,2-6,11H2,1H3

> <INCHI_KEY>
ZTJORNVITHUQJA-UHFFFAOYSA-N

> <FORMULA>
C14H20O3

> <MOLECULAR_WEIGHT>
236.3068

> <EXACT_MASS>
236.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.809030355530528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
heptyl 4-hydroxybenzoate

> <ALOGPS_LOGP>
4.96

> <JCHEM_LOGP>
4.330762468

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.500022184827213

> <JCHEM_PKA_STRONGEST_BASIC>
-6.06441080913955

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
67.74080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
heptylparaben

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034462
     RDKit          3D
Heptyl 4-hydroxybenzoate
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.2773    1.9632   -0.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5594    0.6898   -1.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2963   -0.1338   -1.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771   -0.4732   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107   -1.2991   -0.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0841   -1.5780    1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1755   -2.3996    1.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726   -1.7968    0.6921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8121   -0.5763    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561    0.0193    2.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9613    0.0188    0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6299   -0.5630   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7138    0.0052   -1.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487    1.2408   -0.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2501    1.8148   -1.4512 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5136    1.8638    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302    1.2418    0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376    2.5033   -1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680    1.7713    0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2116    2.5736   -0.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3324    0.1268   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0191    0.9384   -2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438   -1.0864   -2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352    0.3853   -2.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764    0.5036    0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5303   -0.9438    0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975   -0.7226   -0.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -2.2723   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -2.1754    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986   -0.6096    1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -3.3536    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3471   -2.6862    2.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2884   -1.5231   -1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2388   -0.4509   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911    2.4248   -2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8968    2.8170    0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9306    1.7419    1.6562 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  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  12.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  12.320   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667   7.700   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  10.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5   11                                                       
CONECT    7    9   12                                                       
CONECT    8   10   12                                                       
CONECT    9    7   13                                                       
CONECT   10    8   13                                                       
CONECT   11    6   17                                                       
CONECT   12    7    8   14                                                  
CONECT   13    9   10   15                                                  
CONECT   14   12   16   17                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
CONECT   17   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0034462
HETATM    1  C1  UNL     1      -4.277   1.963  -0.551  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.559   0.690  -1.317  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.296  -0.134  -1.497  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.777  -0.473  -0.117  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.511  -1.299  -0.184  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.084  -1.578   1.236  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.175  -2.400   1.303  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.273  -1.797   0.692  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.812  -0.576   1.056  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.256   0.019   2.013  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.961   0.019   0.389  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.630  -0.563  -0.665  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.714   0.005  -1.289  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.149   1.241  -0.815  1.00  0.00           C  
HETATM   15  O3  UNL     1       6.250   1.815  -1.451  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.514   1.864   0.237  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.430   1.242   0.822  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.438   2.503  -1.074  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.068   1.771   0.503  1.00  0.00           H  
HETATM   20  H3  UNL     1      -5.212   2.574  -0.587  1.00  0.00           H  
HETATM   21  H4  UNL     1      -5.332   0.127  -0.756  1.00  0.00           H  
HETATM   22  H5  UNL     1      -5.019   0.938  -2.300  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.544  -1.086  -2.008  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.535   0.385  -2.075  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.476   0.504   0.358  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.530  -0.944   0.518  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.697  -0.723  -0.661  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.679  -2.272  -0.699  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.891  -2.175   1.709  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.999  -0.610   1.752  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.031  -3.354   0.758  1.00  0.00           H  
HETATM   32  H15 UNL     1       0.347  -2.686   2.356  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.288  -1.523  -1.029  1.00  0.00           H  
HETATM   34  H17 UNL     1       5.239  -0.451  -2.116  1.00  0.00           H  
HETATM   35  H18 UNL     1       6.091   2.425  -2.244  1.00  0.00           H  
HETATM   36  H19 UNL     1       4.897   2.817   0.557  1.00  0.00           H  
HETATM   37  H20 UNL     1       2.931   1.742   1.656  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   17
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15   16
CONECT   15   35
CONECT   16   17   17   36
CONECT   17   37
END

HMDB0034462
     RDKit          3D
Heptyl 4-hydroxybenzoate
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.2773    1.9632   -0.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5594    0.6898   -1.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2963   -0.1338   -1.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771   -0.4732   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107   -1.2991   -0.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0841   -1.5780    1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1755   -2.3996    1.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726   -1.7968    0.6921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8121   -0.5763    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561    0.0193    2.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9613    0.0188    0.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6299   -0.5630   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7138    0.0052   -1.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1487    1.2408   -0.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2501    1.8148   -1.4512 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5136    1.8638    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302    1.2418    0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376    2.5033   -1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680    1.7713    0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2116    2.5736   -0.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3324    0.1268   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0191    0.9384   -2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438   -1.0864   -2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352    0.3853   -2.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764    0.5036    0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5303   -0.9438    0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975   -0.7226   -0.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -2.2723   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -2.1754    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986   -0.6096    1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -3.3536    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3471   -2.6862    2.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2884   -1.5231   -1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2388   -0.4509   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911    2.4248   -2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8968    2.8170    0.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9306    1.7419    1.6562 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  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Heptylparaben	Kegg
Heptyl 4-hydroxybenzoic acid	Generator
Benzoic acid, 4-hydroxy-, heptyl ester	HMDB
Benzoic acid, 4-hydroxy-, N-heptyl ester	HMDB
Benzoic acid, P-hydroxy-, heptyl ester	HMDB
Heptyl P-hydroxy benzoate	HMDB
Heptyl P-hydroxybenzoate	HMDB
Heptyl paraben	HMDB
N-Heptyl 4-hydroxybenzoate	HMDB
N-Heptyl P-hydroxybenzoate	HMDB
Nipaheptyl	HMDB
P-Hydroxybenzoic acid heptyl ester	HMDB
staypro WS 7	HMDB
Heptyl p-hydroxybenzoic acid	Generator

Chemical Formula

C₁₄H₂₀O₃

Average Molecular Weight

236.3068

Monoisotopic Molecular Weight

236.141244506

IUPAC Name

heptyl 4-hydroxybenzoate

Traditional Name

heptylparaben

CAS Registry Number

1085-12-7

SMILES

CCCCCCCOC(=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C14H20O3/c1-2-3-4-5-6-11-17-14(16)12-7-9-13(15)10-8-12/h7-10,15H,2-6,11H2,1H3

InChI Key

ZTJORNVITHUQJA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

p-Hydroxybenzoic acid alkyl esters

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoate ester (CHEBI:34788 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034462)
Cell membrane (HMDB: HMDB0034462)

Source

Exogenous

Exogenous (HMDB: HMDB0034462)

Food

Food (HMDB: HMDB0034462)

Process

Not Available

Role

Industrial application

Food and nutrition

Food and nutrition (HMDB: HMDB0034462)

Biological role

Nutrient (HMDB: HMDB0034462)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	49 - 51 °C	Not Available
Boiling Point	353.63 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.02 mg/mL at 30 °C	Not Available
LogP	4.83	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.035 g/L	ALOGPS
logP	4.96	ALOGPS
logP	4.33	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	67.74 m³·mol⁻¹	ChemAxon
Polarizability	27.81 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]+	157.408	31661259
DarkChem	[M-H]-	156.453	31661259
DeepCCS	[M+H]+	161.937	30932474
DeepCCS	[M-H]-	158.817	30932474
DeepCCS	[M-2H]-	194.437	30932474
DeepCCS	[M+Na]+	170.595	30932474
AllCCS	[M+H]+	156.4	32859911
AllCCS	[M+H-H2O]+	152.9	32859911
AllCCS	[M+NH4]+	159.7	32859911
AllCCS	[M+Na]+	160.6	32859911
AllCCS	[M-H]-	160.4	32859911
AllCCS	[M+Na-2H]-	161.1	32859911
AllCCS	[M+HCOO]-	161.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.83 minutes	32390414
Predicted by Siyang on May 30, 2022	17.3355 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.19 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2650.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	512.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	213.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	293.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	481.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	839.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	768.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1562.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	517.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1634.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	553.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	505.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	484.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	385.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	20.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heptyl 4-hydroxybenzoate	CCCCCCCOC(=O)C1=CC=C(O)C=C1	2850.0	Standard polar	33892256
Heptyl 4-hydroxybenzoate	CCCCCCCOC(=O)C1=CC=C(O)C=C1	1951.7	Standard non polar	33892256
Heptyl 4-hydroxybenzoate	CCCCCCCOC(=O)C1=CC=C(O)C=C1	2076.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heptyl 4-hydroxybenzoate,1TMS,isomer #1	CCCCCCCOC(=O)C1=CC=C(O[Si](C)(C)C)C=C1	2082.7	Semi standard non polar	33892256
Heptyl 4-hydroxybenzoate,1TBDMS,isomer #1	CCCCCCCOC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2292.9	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 - Heptyl 4-hydroxybenzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-d6701309efb7422d3d18	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heptyl 4-hydroxybenzoate GC-MS (1 TMS) - 70eV, Positive	splash10-0006-6900000000-f1d3af9e0c68bafdb44f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heptyl 4-hydroxybenzoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0079-5900000000-3d83e4cf98254eb3e062	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 - Heptyl 4-hydroxybenzoate 90V, Negative-QTOF	splash10-0006-9300000000-04df92f5b7ea8aee4cc2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 75V, Negative-QTOF	splash10-0006-9300000000-462e81e1a1b1d6e11915	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 15V, Negative-QTOF	splash10-000i-0090000000-a25d515550160be98efe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 30V, Negative-QTOF	splash10-000i-1390000000-02444847a35bf78a72ad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 60V, Negative-QTOF	splash10-0006-9500000000-eef56f5be2f6dffba5b6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 45V, Negative-QTOF	splash10-000i-6920000000-4d0caf07016ac7adc281	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 10V, Positive-QTOF	splash10-000i-3390000000-9d5d7a09a34e5154f037	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 20V, Positive-QTOF	splash10-006t-9410000000-630af20fa929cdb0263f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 40V, Positive-QTOF	splash10-006x-9200000000-a3b5b661554d8ef165c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 10V, Negative-QTOF	splash10-000i-2390000000-cb5171ec4305db7885a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 20V, Negative-QTOF	splash10-000i-4920000000-ee414667448b4c454b78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 40V, Negative-QTOF	splash10-00ko-9400000000-7b1ffd799d20e79a4077	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 10V, Positive-QTOF	splash10-000i-2690000000-1b18cc5b280969e4eaa5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 20V, Positive-QTOF	splash10-00di-5900000000-7e746c44ef2dfcda9e49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 40V, Positive-QTOF	splash10-00di-9600000000-149b8353bc9688d4bdbf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 10V, Negative-QTOF	splash10-000i-0190000000-78db36f57f97d1bbfa73	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 20V, Negative-QTOF	splash10-0006-9300000000-9cd7041d6f91d1409a33	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptyl 4-hydroxybenzoate 40V, Negative-QTOF	splash10-0006-9100000000-1bc7095d8bbc3de55a80	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB012871

KNApSAcK ID

Not Available

Chemspider ID

13515

KEGG Compound ID

C14718

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14138

PDB ID

Not Available

ChEBI ID

17879

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1438321

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Heptyl 4-hydroxybenzoate (HMDB0034462)

MOL for HMDB0034462 (Heptyl 4-hydroxybenzoate)

3D MOL for HMDB0034462 (Heptyl 4-hydroxybenzoate)

3D SDF for HMDB0034462 (Heptyl 4-hydroxybenzoate)

3D-SDF for HMDB0034462 (Heptyl 4-hydroxybenzoate)

PDB for HMDB0034462 (Heptyl 4-hydroxybenzoate)

3D PDB for HMDB0034462 (Heptyl 4-hydroxybenzoate)

SMILES for HMDB0034462 (Heptyl 4-hydroxybenzoate)

INCHI for HMDB0034462 (Heptyl 4-hydroxybenzoate)

Structure for HMDB0034462 (Heptyl 4-hydroxybenzoate)

3D Structure for HMDB0034462 (Heptyl 4-hydroxybenzoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra