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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-11 02:23:41 UTC

Update Date

2019-07-23 07:17:29 UTC

HMDB ID

HMDB0061942

Secondary Accession Numbers

HMDB61942

Metabolite Identification

Common Name

cis-3-Hexenyl salicylate

Description

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. cis-3-Hexenyl salicylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0061942
     RDKit          3D
cis-3-Hexenyl salicylate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -5.1244   -1.7327   -0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0859   -0.6966   -1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7798   -1.2998   -1.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8413   -0.8171   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    0.3742    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719    1.4081    0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3080    0.8428    0.3296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4756    1.4859    0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943    2.6404   -0.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7897    0.9206    0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9184    1.6786   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1885    1.2079    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3983   -0.0442    0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3318   -0.8160    1.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0336   -0.3010    0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222   -1.1330    1.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0683   -1.2576   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2073   -2.5111   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6888   -2.2527    0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3018   -0.6006   -2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2794    0.2803   -0.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -2.2174   -1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446   -1.3085   -0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7397    0.1906    1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9596    0.9024    0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107    2.3698    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1142    1.5210   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861    2.6748   -0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0779    1.7623   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4115   -0.4294    0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -1.7922    1.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0549   -1.0496    1.1950 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 10101422242D          

 16 16  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    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
    5.0012    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    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
    3.5723    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    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
  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
M  END
> <DATABASE_ID>
HMDB0061942

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/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-ARJAWSKDSA-N

> <FORMULA>
C13H16O3

> <MOLECULAR_WEIGHT>
220.2643

> <EXACT_MASS>
220.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.321295279854603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061942
     RDKit          3D
cis-3-Hexenyl salicylate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -5.1244   -1.7327   -0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0859   -0.6966   -1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7798   -1.2998   -1.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8413   -0.8171   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    0.3742    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719    1.4081    0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3080    0.8428    0.3296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4756    1.4859    0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943    2.6404   -0.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7897    0.9206    0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9184    1.6786   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1885    1.2079    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3983   -0.0442    0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3318   -0.8160    1.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0336   -0.3010    0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222   -1.1330    1.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0683   -1.2576   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2073   -2.5111   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6888   -2.2527    0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3018   -0.6006   -2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2794    0.2803   -0.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -2.2174   -1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446   -1.3085   -0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7397    0.1906    1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9596    0.9024    0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107    2.3698    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1142    1.5210   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861    2.6748   -0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0779    1.7623   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4115   -0.4294    0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -1.7922    1.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0549   -1.0496    1.1950 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                                 10-OCT-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-14         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   8.470   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
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
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                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0061942
HETATM    1  C1  UNL     1      -5.124  -1.733  -0.716  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.086  -0.697  -1.166  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.780  -1.300  -1.039  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.841  -0.817  -0.265  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.020   0.374   0.545  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.972   1.408   0.100  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.308   0.843   0.330  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.476   1.486   0.032  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.394   2.640  -0.476  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.790   0.921   0.266  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.918   1.679  -0.098  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.188   1.208   0.080  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.398  -0.044   0.632  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.332  -0.816   1.001  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.034  -0.301   0.804  1.00  0.00           C  
HETATM   16  O3  UNL     1       2.022  -1.133   1.201  1.00  0.00           O  
HETATM   17  H1  UNL     1      -6.068  -1.258  -0.443  1.00  0.00           H  
HETATM   18  H2  UNL     1      -5.207  -2.511  -1.501  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.689  -2.253   0.182  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.302  -0.601  -2.283  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.279   0.280  -0.768  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.545  -2.217  -1.620  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.845  -1.309  -0.193  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.740   0.191   1.635  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.960   0.902   0.508  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.111   2.370   0.647  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.114   1.521  -0.988  1.00  0.00           H  
HETATM   28  H12 UNL     1       3.786   2.675  -0.538  1.00  0.00           H  
HETATM   29  H13 UNL     1       6.078   1.762  -0.188  1.00  0.00           H  
HETATM   30  H14 UNL     1       6.411  -0.429   0.779  1.00  0.00           H  
HETATM   31  H15 UNL     1       4.492  -1.792   1.431  1.00  0.00           H  
HETATM   32  H16 UNL     1       1.055  -1.050   1.195  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

HMDB0061942
     RDKit          3D
cis-3-Hexenyl salicylate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -5.1244   -1.7327   -0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0859   -0.6966   -1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7798   -1.2998   -1.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8413   -0.8171   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    0.3742    0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719    1.4081    0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3080    0.8428    0.3296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4756    1.4859    0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943    2.6404   -0.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7897    0.9206    0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9184    1.6786   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1885    1.2079    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3983   -0.0442    0.6319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3318   -0.8160    1.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0336   -0.3010    0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222   -1.1330    1.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0683   -1.2576   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2073   -2.5111   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6888   -2.2527    0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3018   -0.6006   -2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2794    0.2803   -0.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449   -2.2174   -1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446   -1.3085   -0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7397    0.1906    1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9596    0.9024    0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107    2.3698    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1142    1.5210   -0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861    2.6748   -0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0779    1.7623   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4115   -0.4294    0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -1.7922    1.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0549   -1.0496    1.1950 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
cis-3-Hexenyl salicylic acid	Generator
3-Hexenyl salicylate, (e)-isomer	HMDB
3-Hexenyl salicylate	HMDB
(3Z)-Hex-3-en-1-yl 2-hydroxybenzoic acid	Generator

Chemical Formula

C₁₃H₁₆O₃

Average Molecular Weight

220.2643

Monoisotopic Molecular Weight

220.109944378

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC\C=C/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-ARJAWSKDSA-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: 20809147)

Source

Exogenous

Exogenous (HMDB: HMDB0061942)

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	24.32 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
DeepCCS	[M+H]+	153.92	30932474
DeepCCS	[M-H]-	151.562	30932474
DeepCCS	[M-2H]-	185.89	30932474
DeepCCS	[M+Na]+	161.275	30932474
AllCCS	[M+H]+	151.1	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 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.	8.78 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4176 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2623.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	451.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	298.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	440.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	752.3 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	747.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1434.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	525.3 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	1479.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	497.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	539.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	428.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	332.8 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	12.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-3-Hexenyl salicylate	CC\C=C/CCOC(=O)C1=CC=CC=C1O	2371.5	Standard polar	33892256
cis-3-Hexenyl salicylate	CC\C=C/CCOC(=O)C1=CC=CC=C1O	1696.4	Standard non polar	33892256
cis-3-Hexenyl salicylate	CC\C=C/CCOC(=O)C1=CC=CC=C1O	1740.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-3-Hexenyl salicylate,1TMS,isomer #1	CC/C=C\CCOC(=O)C1=CC=CC=C1O[Si](C)(C)C	1833.7	Semi standard non polar	33892256
cis-3-Hexenyl salicylate,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
Experimental GC-MS	GC-MS Spectrum - cis-3-Hexenyl salicylate EI-B (Non-derivatized)	splash10-00yi-9300000000-fd064cad5f590089b816	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - cis-3-Hexenyl salicylate EI-B (Non-derivatized)	splash10-00yi-9300000000-fd064cad5f590089b816	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-3-Hexenyl salicylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-f1045e1c3e9d37526e91	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-3-Hexenyl salicylate GC-MS (1 TMS) - 70eV, Positive	splash10-0006-5900000000-66ff71ab7da7411e7267	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-3-Hexenyl salicylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-3-Hexenyl salicylate 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 - cis-3-Hexenyl salicylate 10V, Positive-QTOF	splash10-00di-5490000000-3969028aebe51d411964	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 20V, Positive-QTOF	splash10-0089-9310000000-a206aa1fa5f8b968bc42	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 40V, Positive-QTOF	splash10-0fdo-9200000000-b6c075772626ebbb6eea	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 10V, Negative-QTOF	splash10-014i-3390000000-916271a409795bce3f74	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 20V, Negative-QTOF	splash10-00ko-9820000000-1964ec1ba183ba075130	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 40V, Negative-QTOF	splash10-0006-9100000000-2743837cc64958ae3c42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 10V, Positive-QTOF	splash10-00di-0930000000-9fa9ee9b460183a90355	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 20V, Positive-QTOF	splash10-00di-3900000000-318243c530965998a5f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 40V, Positive-QTOF	splash10-0adi-9300000000-2b251f0254dea9a92e77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 10V, Negative-QTOF	splash10-014l-6290000000-19965aed4eb3c8f1e319	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 20V, Negative-QTOF	splash10-0006-9200000000-9ba8c888cfe721064947	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-3-Hexenyl salicylate 40V, Negative-QTOF	splash10-0006-9000000000-b73e8de79e5d1ff289dd	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)	Both	Normal	20809147	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

5371102

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

van Ketel WG: Sensitization to cis-3-hexenyl salicylate. Contact Dermatitis. 1983 Mar;9(2):154. [PubMed:6851526 ]
Moon JH, Watanabe N, Ijima Y, Yagi A, Sakata K: Cis- and trans-linalool 3,7-oxides and methyl salicylate glycosides and (Z)-3-hexenyl beta-D-glucopyranoside as aroma precursors from tea leaves for oolong tea. Biosci Biotechnol Biochem. 1996 Nov;60(11):1815-9. [PubMed:8987857 ]
James DG: Further field evaluation of synthetic herbivore-induced plant volatiles as attractants for beneficial insects. J Chem Ecol. 2005 Mar;31(3):481-95. [PubMed:15898496 ]
Shaw DW: Allergic contact dermatitis from octisalate and cis-3-hexenyl salicylate. Dermatitis. 2006 Sep;17(3):152-5. [PubMed:16956469 ]
Lapczynski A, McGinty D, Jones L, Letizia CS, Api AM: Fragrance material review on cis-3-hexenyl salicylate. Food Chem Toxicol. 2007;45 Suppl 1:S402-5. Epub 2007 Sep 14. [PubMed:18035471 ]
Ballhorn DJ, Kautz S, Lion U, Heil M: Qualitative variability of lima bean's VOC bouquets and its putative ecological consequences. Plant Signal Behav. 2008 Nov;3(11):1005-7. [PubMed:19704435 ]
Hegde M, Oliveira JN, da Costa JG, Loza-Reyes E, Bleicher E, Santana AE, Caulfield JC, Mayon P, Dewhirst SY, Bruce TJ, Pickett JA, Birkett MA: Aphid antixenosis in cotton is activated by the natural plant defence elicitor cis-jasmone. Phytochemistry. 2012 Jun;78:81-8. doi: 10.1016/j.phytochem.2012.03.004. Epub 2012 Apr 18. [PubMed:22516741 ]
Umasankar Y, Ramasamy RP: Highly sensitive electrochemical detection of methyl salicylate using electroactive gold nanoparticles. Analyst. 2013 Nov 7;138(21):6623-31. doi: 10.1039/c3an01295f. [PubMed:24040645 ]
John Behan, David Bradshaw, Jonathan Richards, Michael Munroe, 'Flavour compositions.' U.S. Patent US20060153959, issued July 13, 2006. [Link]

Showing metabocard for cis-3-Hexenyl salicylate (HMDB0061942)

MOL for HMDB0061942 (cis-3-Hexenyl salicylate)

3D MOL for HMDB0061942 (cis-3-Hexenyl salicylate)

3D SDF for HMDB0061942 (cis-3-Hexenyl salicylate)

3D-SDF for HMDB0061942 (cis-3-Hexenyl salicylate)

PDB for HMDB0061942 (cis-3-Hexenyl salicylate)

3D PDB for HMDB0061942 (cis-3-Hexenyl salicylate)

SMILES for HMDB0061942 (cis-3-Hexenyl salicylate)

INCHI for HMDB0061942 (cis-3-Hexenyl salicylate)

Structure for HMDB0061942 (cis-3-Hexenyl salicylate)

3D Structure for HMDB0061942 (cis-3-Hexenyl salicylate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra