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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:56:05 UTC

Update Date

2022-03-07 03:17:48 UTC

HMDB ID

HMDB0061861

Secondary Accession Numbers

HMDB61861

Metabolite Identification

Common Name

Octyl 4-methoxycinnamic acid

Description

Octyl 4-methoxycinnamic acid, also known as parsol or 2-ethylhexyl-4-methoxycinnamate, belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Octyl 4-methoxycinnamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Its use in pharmaceutical and cosmetic formulations is approved by FDA. Acts as a photoprotective agent that protects the skin by preventing and minimizing the damaging effects of ultraviolet (UV) rays of natural light. It was originally developed in 1950's as an organic UV-B filter that absorbs UV-B rays from sun. Like any other photoprotective agents, octinoxate prevents the damage to cells and deoxyribonucleic acid (DNA) by reducing the p53 protein expression following UV exposure and also increases the skin's tolerability to UV rays . UV-induced molecular breakdown of octinoxate may interfere with cellular processes or induce oxidative damage in human skin . Can be enzymatically degraded by lipases in the stratum corneum where esters undergo hydrolysis . Octinoxate is a cinnamate ester and common ingredient in sunscreen and other skin care products to minimize DNA photodamage. Absorbs UV-B (predominantly) and UV-A rays while accumulating in the outermost layer of the epidermis.

Structure

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

HMDB0061861
     RDKit          3D
Octyl 4-methoxycinnamic acid
 47 47  0  0  0  0  0  0  0  0999 V2000
   -5.1043    1.0114   -1.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9560    0.7107   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5904   -0.4090    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3269   -0.3176    1.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0305   -0.3002    0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8438   -1.5042   -0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -1.5320   -1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9997    0.0503    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6715    0.1037    1.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1785   -0.9631    1.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997   -2.1436    1.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6019   -0.8139    0.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1142    0.3555    0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5071    0.5881    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9371    1.8846   -0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2467    2.1586   -0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1499    1.1258   -0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4616    1.3586   -0.8978 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4461    0.3753   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7317   -0.1483   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4325   -0.4190    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7848    1.3142   -2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612    0.1472   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4554    1.9154   -1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0527    0.6592   -0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9329    1.6495    0.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4226   -0.4531    1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7169   -1.3820    0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1880   -1.1252    2.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2918    0.6275    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0042    0.5850   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6809   -2.3753    0.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710   -1.8324   -0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0118   -1.6872   -2.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9502   -2.3547   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874   -0.5196   -1.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801    1.0453    1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157   -0.6513    2.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208   -1.6719    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344    1.2102    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485    2.7204   -0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5834    3.1610   -0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2149   -0.2258   -1.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4279    0.8605   -1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630   -0.3318   -0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4241   -1.0045   -0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1502   -1.4522    0.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21 14  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
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
 12 39  1  0
 13 40  1  0
 15 41  1  0
 16 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
M  END


  Mrv0541 10081412332D          

 23 23  0  0  0  0            999 V2000
   -4.2868    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    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    7.4250    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
   -2.1434    6.1875    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
    2.8579    7.4250    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
    4.2868    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.6000    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
    4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   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
    5.0013    7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  2  0  0  0  0
 15  5  1  0  0  0  0
 15  7  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19 18  2  0  0  0  0
 20  3  1  0  0  0  0
 20 17  1  0  0  0  0
 21 14  1  0  0  0  0
 21 18  1  0  0  0  0
 22 10  1  0  0  0  0
 23 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061861

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(=C(\[H])C1=CC=C(OC)C=C1)C(=O)OCC(CC)CCCC

> <INCHI_IDENTIFIER>
InChI=1S/C18H26O3/c1-4-6-7-15(5-2)14-21-18(19)13-10-16-8-11-17(20-3)12-9-16/h8-13,15H,4-7,14H2,1-3H3/b13-10+

> <INCHI_KEY>
YBGZDTIWKVFICR-JLHYYAGUSA-N

> <FORMULA>
C18H26O3

> <MOLECULAR_WEIGHT>
290.3972

> <EXACT_MASS>
290.188194698

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
34.83771507939504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-ethylhexyl (2E)-3-(4-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
5.62

> <JCHEM_LOGP>
5.380220219666667

> <ALOGPS_LOGS>
-5.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.819479599848811

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
86.4404

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
parsol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061861
     RDKit          3D
Octyl 4-methoxycinnamic acid
 47 47  0  0  0  0  0  0  0  0999 V2000
   -5.1043    1.0114   -1.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9560    0.7107   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5904   -0.4090    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3269   -0.3176    1.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0305   -0.3002    0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8438   -1.5042   -0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -1.5320   -1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9997    0.0503    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6715    0.1037    1.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1785   -0.9631    1.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997   -2.1436    1.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6019   -0.8139    0.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1142    0.3555    0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5071    0.5881    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9371    1.8846   -0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2467    2.1586   -0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1499    1.1258   -0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4616    1.3586   -0.8978 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4461    0.3753   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7317   -0.1483   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4325   -0.4190    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7848    1.3142   -2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612    0.1472   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4554    1.9154   -1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0527    0.6592   -0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9329    1.6495    0.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4226   -0.4531    1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7169   -1.3820    0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1880   -1.1252    2.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2918    0.6275    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0042    0.5850   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6809   -2.3753    0.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710   -1.8324   -0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0118   -1.6872   -2.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9502   -2.3547   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874   -0.5196   -1.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801    1.0453    1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157   -0.6513    2.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208   -1.6719    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344    1.2102    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485    2.7204   -0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5834    3.1610   -0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2149   -0.2258   -1.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4279    0.8605   -1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630   -0.3318   -0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4241   -1.0045   -0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1502   -1.4522    0.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21 14  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
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
 12 39  1  0
 13 40  1  0
 15 41  1  0
 16 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
M  END

HEADER    PROTEIN                                 08-OCT-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-14         0                                  
HETATM    1  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  14.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  16.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  14.630   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334  10.010   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336  14.630   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000  12.320   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       4.001  10.010   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.667  13.860   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3   20                                                            
CONECT    4    1    6                                                       
CONECT    5    2   15                                                       
CONECT    6    4    7                                                       
CONECT    7    6   15                                                       
CONECT    8   11   16                                                       
CONECT    9   12   16                                                       
CONECT   10   13   16   22                                                  
CONECT   11    8   17                                                       
CONECT   12    9   17                                                       
CONECT   13   10   18   23                                                  
CONECT   14   15   21                                                       
CONECT   15    5    7   14                                                  
CONECT   16    8    9   10                                                  
CONECT   17   11   12   20                                                  
CONECT   18   13   19   21                                                  
CONECT   19   18                                                            
CONECT   20    3   17                                                       
CONECT   21   14   18                                                       
CONECT   22   10                                                            
CONECT   23   13                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0061861
HETATM    1  C1  UNL     1      -5.104   1.011  -1.487  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.956   0.711  -0.318  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.590  -0.409   0.589  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.327  -0.318   1.309  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.031  -0.300   0.509  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.844  -1.504  -0.303  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.644  -1.532  -1.212  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.000   0.050   1.554  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.672   0.104   1.257  1.00  0.00           O  
HETATM   10  C9  UNL     1       0.178  -0.963   1.205  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.200  -2.144   1.469  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.602  -0.814   0.839  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.114   0.355   0.545  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.507   0.588   0.173  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.937   1.885  -0.120  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.247   2.159  -0.477  1.00  0.00           C  
HETATM   17  C15 UNL     1       6.150   1.126  -0.546  1.00  0.00           C  
HETATM   18  O3  UNL     1       7.462   1.359  -0.898  1.00  0.00           O  
HETATM   19  C16 UNL     1       8.446   0.375  -0.994  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.732  -0.148  -0.259  1.00  0.00           C  
HETATM   21  C18 UNL     1       4.433  -0.419   0.095  1.00  0.00           C  
HETATM   22  H1  UNL     1      -5.785   1.314  -2.350  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.561   0.147  -1.875  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.455   1.915  -1.368  1.00  0.00           H  
HETATM   25  H4  UNL     1      -7.053   0.659  -0.588  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.933   1.650   0.336  1.00  0.00           H  
HETATM   27  H6  UNL     1      -6.423  -0.453   1.364  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.717  -1.382   0.025  1.00  0.00           H  
HETATM   29  H8  UNL     1      -4.188  -1.125   2.084  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.292   0.628   1.932  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.004   0.585  -0.194  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.681  -2.375   0.414  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.771  -1.832  -0.846  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.012  -1.687  -2.282  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.950  -2.355  -1.060  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.187  -0.520  -1.210  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.380   1.045   1.995  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.216  -0.651   2.432  1.00  0.00           H  
HETATM   39  H18 UNL     1       2.221  -1.672   0.813  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.434   1.210   0.585  1.00  0.00           H  
HETATM   41  H20 UNL     1       3.248   2.720  -0.074  1.00  0.00           H  
HETATM   42  H21 UNL     1       5.583   3.161  -0.704  1.00  0.00           H  
HETATM   43  H22 UNL     1       8.215  -0.226  -1.918  1.00  0.00           H  
HETATM   44  H23 UNL     1       9.428   0.861  -1.097  1.00  0.00           H  
HETATM   45  H24 UNL     1       8.463  -0.332  -0.137  1.00  0.00           H  
HETATM   46  H25 UNL     1       6.424  -1.004  -0.303  1.00  0.00           H  
HETATM   47  H26 UNL     1       4.150  -1.452   0.314  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6    8   31
CONECT    6    7   32   33
CONECT    7   34   35   36
CONECT    8    9   37   38
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   13   39
CONECT   13   14   40
CONECT   14   15   15   21
CONECT   15   16   41
CONECT   16   17   17   42
CONECT   17   18   20
CONECT   18   19
CONECT   19   43   44   45
CONECT   20   21   21   46
CONECT   21   47
END

HMDB0061861
     RDKit          3D
Octyl 4-methoxycinnamic acid
 47 47  0  0  0  0  0  0  0  0999 V2000
   -5.1043    1.0114   -1.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9560    0.7107   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5904   -0.4090    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3269   -0.3176    1.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0305   -0.3002    0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8438   -1.5042   -0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -1.5320   -1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9997    0.0503    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6715    0.1037    1.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1785   -0.9631    1.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997   -2.1436    1.4686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6019   -0.8139    0.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1142    0.3555    0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5071    0.5881    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9371    1.8846   -0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2467    2.1586   -0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1499    1.1258   -0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4616    1.3586   -0.8978 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4461    0.3753   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7317   -0.1483   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4325   -0.4190    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7848    1.3142   -2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5612    0.1472   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4554    1.9154   -1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0527    0.6592   -0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9329    1.6495    0.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4226   -0.4531    1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7169   -1.3820    0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1880   -1.1252    2.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2918    0.6275    1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0042    0.5850   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6809   -2.3753    0.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710   -1.8324   -0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0118   -1.6872   -2.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9502   -2.3547   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874   -0.5196   -1.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801    1.0453    1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157   -0.6513    2.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208   -1.6719    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344    1.2102    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485    2.7204   -0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5834    3.1610   -0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2149   -0.2258   -1.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4279    0.8605   -1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630   -0.3318   -0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4241   -1.0045   -0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1502   -1.4522    0.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21 14  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
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
 12 39  1  0
 13 40  1  0
 15 41  1  0
 16 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Octyl methoxycinnamate	Kegg
Parsol	Kegg
Octyl methoxycinnamic acid	Generator
Octyl 4-methoxycinnamate	Generator
OCTINOXic acid	HMDB
Heliopan new	HMDB
OMC cinnamate	HMDB
Parsol MCX	HMDB
Octylmethoxycinnamate	HMDB
2-Ethylhexyl-4-methoxycinnamate	HMDB
2-Ethylhexyl-p-methoxycinnamate	HMDB
Escalol 557	HMDB
Octyl-methoxycinnamate	HMDB

Chemical Formula

C₁₈H₂₆O₃

Average Molecular Weight

290.3972

Monoisotopic Molecular Weight

290.188194698

IUPAC Name

2-ethylhexyl (2E)-3-(4-methoxyphenyl)prop-2-enoate

Traditional Name

parsol

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=C(OC)C=C1)C(=O)OCC(CC)CCCC

InChI Identifier

InChI=1S/C18H26O3/c1-4-6-7-15(5-2)14-21-18(19)13-10-16-8-11-17(20-3)12-9-16/h8-13,15H,4-7,14H2,1-3H3/b13-10+

InChI Key

YBGZDTIWKVFICR-JLHYYAGUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Process

Not Available

Role

Not Available

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
Water Solubility	0.00045 g/L	ALOGPS
logP	5.62	ALOGPS
logP	5.38	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	86.44 m³·mol⁻¹	ChemAxon
Polarizability	34.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	174.642	31661259
DarkChem	[M-H]-	176.925	31661259
DeepCCS	[M+H]+	168.216	30932474
DeepCCS	[M-H]-	165.82	30932474
DeepCCS	[M-2H]-	199.791	30932474
DeepCCS	[M+Na]+	174.603	30932474
AllCCS	[M+H]+	174.9	32859911
AllCCS	[M+H-H2O]+	171.9	32859911
AllCCS	[M+NH4]+	177.7	32859911
AllCCS	[M+Na]+	178.5	32859911
AllCCS	[M-H]-	174.7	32859911
AllCCS	[M+Na-2H]-	175.5	32859911
AllCCS	[M+HCOO]-	176.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Octyl 4-methoxycinnamic acid	[H]\C(=C(\[H])C1=CC=C(OC)C=C1)C(=O)OCC(CC)CCCC	2993.3	Standard polar	33892256
Octyl 4-methoxycinnamic acid	[H]\C(=C(\[H])C1=CC=C(OC)C=C1)C(=O)OCC(CC)CCCC	2183.7	Standard non polar	33892256
Octyl 4-methoxycinnamic acid	[H]\C(=C(\[H])C1=CC=C(OC)C=C1)C(=O)OCC(CC)CCCC	2134.0	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 - Octyl 4-methoxycinnamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vi-9530000000-dfb5bc7b1b0717378513	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Octyl 4-methoxycinnamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Octyl 4-methoxycinnamic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 50V, Positive-QTOF	splash10-001i-0900000000-d4a1e41c086413d0cf67	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 50V, Positive-QTOF	splash10-001i-0900000000-47b5b9c89e092811dc9d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 30V, Positive-QTOF	splash10-03di-0900000000-f61c750cc4eee5641214	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 20V, Positive-QTOF	splash10-03di-0900000000-bef6ca3443465e6c192e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 40V, Positive-QTOF	splash10-03e9-0900000000-9b48952b6721ccf2a0d4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 10V, Positive-QTOF	splash10-004i-0900000000-04c530c6956b0f1f054f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 10V, Positive-QTOF	splash10-03dl-0950000000-7c75a171098f061df1d5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 20V, Positive-QTOF	splash10-03di-3910000000-999432b0b3a154dc16c4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 40V, Positive-QTOF	splash10-06r6-9400000000-f0de61dd27ceae8cac50	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 10V, Negative-QTOF	splash10-052r-0970000000-9b1d54a8c418b0e3d7dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 20V, Negative-QTOF	splash10-06vi-0910000000-29fe696309912eb4ba3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 40V, Negative-QTOF	splash10-01r2-3900000000-58e02602b0c98e57a09c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 10V, Positive-QTOF	splash10-01r6-4970000000-a670cd89d51c4faa0f4b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 20V, Positive-QTOF	splash10-08ir-5910000000-378dcd5411abe5d4d831	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 40V, Positive-QTOF	splash10-053u-9200000000-9025b50b69c626ee01d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 10V, Negative-QTOF	splash10-000i-0790000000-dffcbb803f602e4748f9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 20V, Negative-QTOF	splash10-0a4r-0920000000-f1683c652bffc0f2fcad	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl 4-methoxycinnamic acid 40V, Negative-QTOF	splash10-014i-0900000000-17d9a346b3a4b2ac552f	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09496

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

5355130

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lee GS, Widjaja A, Ju YH: Enzymatic synthesis of cinnamic acid derivatives. Biotechnol Lett. 2006 Apr;28(8):581-5. [PubMed:16614896 ]

Showing metabocard for Octyl 4-methoxycinnamic acid (HMDB0061861)

MOL for HMDB0061861 (Octyl 4-methoxycinnamic acid)

3D MOL for HMDB0061861 (Octyl 4-methoxycinnamic acid)

3D SDF for HMDB0061861 (Octyl 4-methoxycinnamic acid)

3D-SDF for HMDB0061861 (Octyl 4-methoxycinnamic acid)

PDB for HMDB0061861 (Octyl 4-methoxycinnamic acid)

3D PDB for HMDB0061861 (Octyl 4-methoxycinnamic acid)

SMILES for HMDB0061861 (Octyl 4-methoxycinnamic acid)

INCHI for HMDB0061861 (Octyl 4-methoxycinnamic acid)

Structure for HMDB0061861 (Octyl 4-methoxycinnamic acid)

3D Structure for HMDB0061861 (Octyl 4-methoxycinnamic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra