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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:55:17 UTC

Update Date

2022-03-07 03:17:47 UTC

HMDB ID

HMDB0061823

Secondary Accession Numbers

HMDB61823

Metabolite Identification

Common Name

3-Hexenyl salicylic acid

Description

3-Hexenyl salicylic acid, also known as cis-3-hexenyl salicylate, belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. 3-Hexenyl salicylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0061823
     RDKit          3D
3-Hexenyl salicylic acid
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.9172   -0.8747    0.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -1.3302    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2075   -0.1539   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9641    0.2712   -0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313    1.4582   -1.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815    1.0781   -2.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7908    0.5088   -1.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    1.1771   -0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0935    2.3459   -0.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764    0.5432    0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2897    1.1531    1.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3309    0.5381    1.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6961   -0.7521    1.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9913   -1.3785    0.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9466   -0.7602   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2569   -1.4246   -1.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5564   -0.4984    1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5930   -1.7294    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4971   -0.0784    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2227   -2.0399   -0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320   -1.8675    0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9040    0.3899   -1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -0.2885    0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2055    2.3077   -0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.8090   -1.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1057    1.9955   -2.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6611    0.4244   -2.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0052    2.1683    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8762    1.0244    2.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5174   -1.2595    2.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010   -2.3921    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5503   -2.3649   -1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
M  END


  Mrv0541 10081412312D          

 18 18  0  0  0  0            999 V2000
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 H   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  2  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  1  0  0  0  0
 16 13  1  0  0  0  0
 17  3  1  0  0  0  0
 18  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061823

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CC)=C(\[H])CCOC(=O)C1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O3/c1-2-3-4-7-10-16-13(15)11-8-5-6-9-12(11)14/h3-6,8-9,14H,2,7,10H2,1H3/b4-3+

> <INCHI_KEY>
IEPWIPZLLIOZLU-ONEGZZNKSA-N

> <FORMULA>
C13H16O3

> <MOLECULAR_WEIGHT>
220.2643

> <EXACT_MASS>
220.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.589896752654955

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-hex-3-en-1-yl 2-hydroxybenzoate

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
4.174272146333333

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.719401359031588

> <JCHEM_PKA_STRONGEST_BASIC>
-4.287633116932644

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
64.25640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hexenyl salicylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061823
     RDKit          3D
3-Hexenyl salicylic acid
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.9172   -0.8747    0.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -1.3302    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2075   -0.1539   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9641    0.2712   -0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313    1.4582   -1.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815    1.0781   -2.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7908    0.5088   -1.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    1.1771   -0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0935    2.3459   -0.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764    0.5432    0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2897    1.1531    1.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3309    0.5381    1.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6961   -0.7521    1.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9913   -1.3785    0.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9466   -0.7602   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2569   -1.4246   -1.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5564   -0.4984    1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5930   -1.7294    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4971   -0.0784    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2227   -2.0399   -0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320   -1.8675    0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9040    0.3899   -1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -0.2885    0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2055    2.3077   -0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.8090   -1.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1057    1.9955   -2.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6611    0.4244   -2.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0052    2.1683    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8762    1.0244    2.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5174   -1.2595    2.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010   -2.3921    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5503   -2.3649   -1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  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      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0      -1.334   8.470   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.000   4.620   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    7   18                                                  
CONECT    5    6    8                                                       
CONECT    6    5    9                                                       
CONECT    7    4   10                                                       
CONECT    8    5   11                                                       
CONECT    9    6   12                                                       
CONECT   10    7   16                                                       
CONECT   11    8   12   13                                                  
CONECT   12    9   11   14                                                  
CONECT   13   11   15   16                                                  
CONECT   14   12                                                            
CONECT   15   13                                                            
CONECT   16   10   13                                                       
CONECT   17    3                                                            
CONECT   18    4                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0061823
HETATM    1  C1  UNL     1       4.917  -0.875   0.983  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.759  -1.330   0.091  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.207  -0.154  -0.618  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.964   0.271  -0.518  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.431   1.458  -1.241  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.282   1.078  -2.153  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.791   0.509  -1.441  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.475   1.177  -0.439  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.093   2.346  -0.179  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.576   0.543   0.266  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.290   1.153   1.264  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.331   0.538   1.922  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.696  -0.752   1.582  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.991  -1.378   0.583  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.947  -0.760  -0.076  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.257  -1.425  -1.081  1.00  0.00           O  
HETATM   17  H1  UNL     1       4.556  -0.498   1.948  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.593  -1.729   1.174  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.497  -0.078   0.476  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.223  -2.040  -0.644  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.032  -1.868   0.693  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.904   0.390  -1.270  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.296  -0.288   0.136  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.205   2.308  -0.582  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.274   1.809  -1.902  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.106   1.995  -2.640  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.661   0.424  -2.954  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.005   2.168   1.534  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.876   1.024   2.696  1.00  0.00           H  
HETATM   30  H14 UNL     1      -5.517  -1.260   2.089  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.301  -2.392   0.338  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.550  -2.365  -1.303  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   11   15
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16
CONECT   16   32
END

HMDB0061823
     RDKit          3D
3-Hexenyl salicylic acid
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.9172   -0.8747    0.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593   -1.3302    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2075   -0.1539   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9641    0.2712   -0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313    1.4582   -1.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815    1.0781   -2.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7908    0.5088   -1.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    1.1771   -0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0935    2.3459   -0.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764    0.5432    0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2897    1.1531    1.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3309    0.5381    1.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6961   -0.7521    1.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9913   -1.3785    0.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9466   -0.7602   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2569   -1.4246   -1.0814 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5564   -0.4984    1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5930   -1.7294    1.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4971   -0.0784    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2227   -2.0399   -0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320   -1.8675    0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9040    0.3899   -1.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -0.2885    0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2055    2.3077   -0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.8090   -1.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1057    1.9955   -2.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6611    0.4244   -2.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0052    2.1683    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8762    1.0244    2.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5174   -1.2595    2.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3010   -2.3921    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5503   -2.3649   -1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hexenyl salicylate	Generator
cis-3-Hexenyl salicylate	HMDB
3-Hexenyl salicylate, (e)-isomer	HMDB

Chemical Formula

C₁₃H₁₆O₃

Average Molecular Weight

220.2643

Monoisotopic Molecular Weight

220.109944378

IUPAC Name

(3E)-hex-3-en-1-yl 2-hydroxybenzoate

Traditional Name

3-hexenyl salicylate

CAS Registry Number

Not Available

SMILES

[H]\C(CC)=C(\[H])CCOC(=O)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C13H16O3/c1-2-3-4-7-10-16-13(15)11-8-5-6-9-12(11)14/h3-6,8-9,14H,2,7,10H2,1H3/b4-3+

InChI Key

IEPWIPZLLIOZLU-ONEGZZNKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

o-Hydroxybenzoic acid esters

Alternative Parents

Substituents

O-hydroxybenzoic acid ester
Salicylic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
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

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	0.36 g/L	ALOGPS
logP	4.08	ALOGPS
logP	4.17	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.72	ChemAxon
pKa (Strongest Basic)	-4.3	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	6	ChemAxon
Refractivity	64.26 m³·mol⁻¹	ChemAxon
Polarizability	24.59 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]+	152.854	31661259
DarkChem	[M-H]-	151.818	31661259
DeepCCS	[M+H]+	150.821	30932474
DeepCCS	[M-H]-	148.463	30932474
DeepCCS	[M-2H]-	181.561	30932474
DeepCCS	[M+Na]+	156.914	30932474
AllCCS	[M+H]+	151.2	32859911
AllCCS	[M+H-H2O]+	147.4	32859911
AllCCS	[M+NH4]+	154.6	32859911
AllCCS	[M+Na]+	155.6	32859911
AllCCS	[M-H]-	154.1	32859911
AllCCS	[M+Na-2H]-	154.6	32859911
AllCCS	[M+HCOO]-	155.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hexenyl salicylic acid	[H]\C(CC)=C(\[H])CCOC(=O)C1=CC=CC=C1O	2723.8	Standard polar	33892256
3-Hexenyl salicylic acid	[H]\C(CC)=C(\[H])CCOC(=O)C1=CC=CC=C1O	1715.5	Standard non polar	33892256
3-Hexenyl salicylic acid	[H]\C(CC)=C(\[H])CCOC(=O)C1=CC=CC=C1O	1678.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hexenyl salicylic acid,1TMS,isomer #1	CC/C=C/CCOC(=O)C1=CC=CC=C1O[Si](C)(C)C	1833.7	Semi standard non polar	33892256
3-Hexenyl salicylic acid,1TBDMS,isomer #1	CC/C=C/CCOC(=O)C1=CC=CC=C1O[Si](C)(C)C(C)(C)C	2064.9	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 - 3-Hexenyl salicylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-9c23698cbe1973b08977	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hexenyl salicylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0006-5900000000-66ff71ab7da7411e7267	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hexenyl salicylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hexenyl salicylic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 10V, Positive-QTOF	splash10-00di-3390000000-8010f528bce1e5ce68cf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 20V, Positive-QTOF	splash10-0089-9410000000-256ae1cd2de192372357	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 40V, Positive-QTOF	splash10-0ukl-9100000000-a09589911e1695c8ead5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 10V, Negative-QTOF	splash10-014i-3390000000-d4badb5c1d6537223293	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 20V, Negative-QTOF	splash10-00ko-9830000000-93338d5791f48a106ea2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 40V, Negative-QTOF	splash10-0006-9100000000-d52a3cdf8eacf5e9f185	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 10V, Negative-QTOF	splash10-014i-2090000000-0695443a95e15e3bdfe3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 20V, Negative-QTOF	splash10-0006-9200000000-630549873e9a0e796852	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 40V, Negative-QTOF	splash10-0006-9000000000-455fb2cdd65dbc5306b2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 10V, Positive-QTOF	splash10-00di-0930000000-007d8e0b7872b79a07dd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 20V, Positive-QTOF	splash10-00di-3900000000-8f88bb9b0194efc09f49	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hexenyl salicylic acid 40V, Positive-QTOF	splash10-0a4i-9100000000-8bb15305aacb84a2123a	2021-09-24	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

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

6021887

PDB ID

Not Available

ChEBI ID

88591

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

Fontana A, Reichelt M, Hempel S, Gershenzon J, Unsicker SB: The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L. J Chem Ecol. 2009 Jul;35(7):833-43. doi: 10.1007/s10886-009-9654-0. Epub 2009 Jul 2. [PubMed:19568812 ]
Liu S, Han B: Differential expression pattern of an acidic 9/13-lipoxygenase in flower opening and senescence and in leaf response to phloem feeders in the tea plant. BMC Plant Biol. 2010 Oct 25;10:228. doi: 10.1186/1471-2229-10-228. [PubMed:20969806 ]
Erb M, Foresti N, Turlings TC: A tritrophic signal that attracts parasitoids to host-damaged plants withstands disruption by non-host herbivores. BMC Plant Biol. 2010 Nov 15;10:247. doi: 10.1186/1471-2229-10-247. [PubMed:21078181 ]
Arimura G, Ozawa R, Maffei ME: Recent advances in plant early signaling in response to herbivory. Int J Mol Sci. 2011;12(6):3723-39. doi: 10.3390/ijms12063723. Epub 2011 Jun 7. [PubMed:21747702 ]
Furstenberg-Hagg J, Zagrobelny M, Bak S: Plant defense against insect herbivores. Int J Mol Sci. 2013 May 16;14(5):10242-97. doi: 10.3390/ijms140510242. [PubMed:23681010 ]
Song GC, Ryu CM: Two volatile organic compounds trigger plant self-defense against a bacterial pathogen and a sucking insect in cucumber under open field conditions. Int J Mol Sci. 2013 May 8;14(5):9803-19. doi: 10.3390/ijms14059803. [PubMed:23698768 ]
Holopainen JK, Blande JD: Where do herbivore-induced plant volatiles go? Front Plant Sci. 2013 Jun 11;4:185. doi: 10.3389/fpls.2013.00185. eCollection 2013. [PubMed:23781224 ]
Niinemets U, Kannaste A, Copolovici L: Quantitative patterns between plant volatile emissions induced by biotic stresses and the degree of damage. Front Plant Sci. 2013 Jul 23;4:262. doi: 10.3389/fpls.2013.00262. eCollection 2013. [PubMed:23888161 ]
Scala A, Allmann S, Mirabella R, Haring MA, Schuurink RC: Green leaf volatiles: a plant's multifunctional weapon against herbivores and pathogens. Int J Mol Sci. 2013 Aug 30;14(9):17781-811. doi: 10.3390/ijms140917781. [PubMed:23999587 ]
Engelberth J, Contreras CF, Dalvi C, Li T, Engelberth M: Early transcriptome analyses of Z-3-Hexenol-treated zea mays revealed distinct transcriptional networks and anti-herbivore defense potential of green leaf volatiles. PLoS One. 2013 Oct 14;8(10):e77465. doi: 10.1371/journal.pone.0077465. eCollection 2013. [PubMed:24155960 ]

Showing metabocard for 3-Hexenyl salicylic acid (HMDB0061823)

MOL for HMDB0061823 (3-Hexenyl salicylic acid)

3D MOL for HMDB0061823 (3-Hexenyl salicylic acid)

3D SDF for HMDB0061823 (3-Hexenyl salicylic acid)

3D-SDF for HMDB0061823 (3-Hexenyl salicylic acid)

PDB for HMDB0061823 (3-Hexenyl salicylic acid)

3D PDB for HMDB0061823 (3-Hexenyl salicylic acid)

SMILES for HMDB0061823 (3-Hexenyl salicylic acid)

INCHI for HMDB0061823 (3-Hexenyl salicylic acid)

Structure for HMDB0061823 (3-Hexenyl salicylic acid)

3D Structure for HMDB0061823 (3-Hexenyl salicylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra