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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:28:21 UTC

Update Date

2023-02-21 17:25:44 UTC

HMDB ID

HMDB0037231

Secondary Accession Numbers

HMDB37231

Metabolite Identification

Common Name

Perillyl acetate

Description

Perillyl acetate belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a significant number of articles have been published on Perillyl acetate.

Structure

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

HMDB0037231
     RDKit          3D
Perillyl acetate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.4816    0.1652   -1.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9396   -0.1023   -0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8283   -0.5792    0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4906    0.0622   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8102   -1.2611    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6630   -0.9729    0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506   -0.0286    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4127    0.4387    1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218   -0.1596    0.4036 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -0.0843   -0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6197   -0.7439   -1.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885    0.5648   -1.6252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    0.6205    1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1912    1.0429    0.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5337    0.0435   -1.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8190    0.5186   -2.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6130   -1.2057    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -1.1572    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3492    0.2859    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0235    0.4673   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0662   -2.0273   -0.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737   -1.6110    1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846   -1.4961   -0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    1.5522    1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    0.2041    2.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0059   -1.6399   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4525   -0.0077   -1.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -0.9446   -2.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4340   -0.0818    2.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3053    1.5276    2.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9391    2.0549    0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0635    1.2357    1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  7 13  1  0
 13 14  1  0
 14  4  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
M  END


  Mrv0541 05061309392D          

 14 14  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  8  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037231

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC1=CCC(CC1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O2/c1-9(2)12-6-4-11(5-7-12)8-14-10(3)13/h4,12H,1,5-8H2,2-3H3

> <INCHI_KEY>
WTXBCFKGCNWPLS-UHFFFAOYSA-N

> <FORMULA>
C12H18O2

> <MOLECULAR_WEIGHT>
194.2701

> <EXACT_MASS>
194.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.385875851294557

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methyl acetate

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
2.3801669053333336

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.005011665906749

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
57.40650000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037231
     RDKit          3D
Perillyl acetate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.4816    0.1652   -1.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9396   -0.1023   -0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8283   -0.5792    0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4906    0.0622   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8102   -1.2611    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6630   -0.9729    0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506   -0.0286    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4127    0.4387    1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218   -0.1596    0.4036 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -0.0843   -0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6197   -0.7439   -1.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885    0.5648   -1.6252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    0.6205    1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1912    1.0429    0.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5337    0.0435   -1.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8190    0.5186   -2.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6130   -1.2057    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -1.1572    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3492    0.2859    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0235    0.4673   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0662   -2.0273   -0.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737   -1.6110    1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846   -1.4961   -0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    1.5522    1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    0.2041    2.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0059   -1.6399   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4525   -0.0077   -1.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -0.9446   -2.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4340   -0.0818    2.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3053    1.5276    2.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9391    2.0549    0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0635    1.2357    1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  7 13  1  0
 13 14  1  0
 14  4  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    6   11                                                       
CONECT    5    7   11                                                       
CONECT    6    4   12                                                       
CONECT    7    5   12                                                       
CONECT    8   11   14                                                       
CONECT    9    1    2   12                                                  
CONECT   10    3   13   14                                                  
CONECT   11    4    5    8                                                  
CONECT   12    6    7    9                                                  
CONECT   13   10                                                            
CONECT   14    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0037231
HETATM    1  C1  UNL     1      -3.482   0.165  -1.697  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.940  -0.102  -0.508  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.828  -0.579   0.585  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.491   0.062  -0.252  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.810  -1.261   0.037  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.663  -0.973   0.079  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.051  -0.029   0.924  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.413   0.439   1.153  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.422  -0.160   0.404  1.00  0.00           O  
HETATM   10  C9  UNL     1       3.530  -0.084  -0.954  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.620  -0.744  -1.739  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.689   0.565  -1.625  1.00  0.00           O  
HETATM   13  C11 UNL     1      -0.041   0.621   1.724  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.191   1.043   0.836  1.00  0.00           C  
HETATM   15  H1  UNL     1      -4.534   0.043  -1.875  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.819   0.519  -2.504  1.00  0.00           H  
HETATM   17  H3  UNL     1      -4.613  -1.206   0.124  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.233  -1.157   1.347  1.00  0.00           H  
HETATM   19  H5  UNL     1      -4.349   0.286   1.061  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.023   0.467  -1.198  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.066  -2.027  -0.703  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.074  -1.611   1.068  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.385  -1.496  -0.525  1.00  0.00           H  
HETATM   24  H10 UNL     1       2.443   1.552   1.120  1.00  0.00           H  
HETATM   25  H11 UNL     1       2.653   0.204   2.234  1.00  0.00           H  
HETATM   26  H12 UNL     1       5.006  -1.640  -1.216  1.00  0.00           H  
HETATM   27  H13 UNL     1       5.453  -0.008  -1.786  1.00  0.00           H  
HETATM   28  H14 UNL     1       4.300  -0.945  -2.770  1.00  0.00           H  
HETATM   29  H15 UNL     1      -0.434  -0.082   2.495  1.00  0.00           H  
HETATM   30  H16 UNL     1       0.305   1.528   2.249  1.00  0.00           H  
HETATM   31  H17 UNL     1      -0.939   2.055   0.407  1.00  0.00           H  
HETATM   32  H18 UNL     1      -2.063   1.236   1.505  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3    4
CONECT    3   17   18   19
CONECT    4    5   14   20
CONECT    5    6   21   22
CONECT    6    7    7   23
CONECT    7    8   13
CONECT    8    9   24   25
CONECT    9   10
CONECT   10   11   12   12
CONECT   11   26   27   28
CONECT   13   14   29   30
CONECT   14   31   32
END

HMDB0037231
     RDKit          3D
Perillyl acetate
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.4816    0.1652   -1.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9396   -0.1023   -0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8283   -0.5792    0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4906    0.0622   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8102   -1.2611    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6630   -0.9729    0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506   -0.0286    0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4127    0.4387    1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218   -0.1596    0.4036 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -0.0843   -0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6197   -0.7439   -1.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885    0.5648   -1.6252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    0.6205    1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1912    1.0429    0.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5337    0.0435   -1.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8190    0.5186   -2.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6130   -1.2057    0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -1.1572    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3492    0.2859    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0235    0.4673   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0662   -2.0273   -0.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737   -1.6110    1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846   -1.4961   -0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    1.5522    1.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    0.2041    2.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0059   -1.6399   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4525   -0.0077   -1.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -0.9446   -2.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4340   -0.0818    2.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3053    1.5276    2.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9391    2.0549    0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0635    1.2357    1.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  7 13  1  0
 13 14  1  0
 14  4  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Perillyl acetic acid	Generator
(4-Isopropenyl-1-cyclohexen-1-yl)methyl acetate	HMDB
1,8-P-Menthadien-7-yl acetate	HMDB
1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-, 1-acetate	HMDB
1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-, acetate	HMDB
4-(1-Methylethenyl)-1-cyclohexene-1-methyl acetate	HMDB
4-(1-Methylvinyl)cyclohex-1-ene-1-methyl acetate	HMDB
4-Isopropenyl-1-cyclohexene carbinyl acetate	HMDB
Cyclohex-1-ene-1-methanol-4-(1-methylethenyl)-acetate	HMDB
Dihydrocuminyl acetate	HMDB
FEMA 3561	HMDB
Menthadien-7-carbinyl acetate	HMDB
P-Mentha-1,8-dien-7-ol, acetate	HMDB
P-Mentha-1,8-dien-7-yl acetate	HMDB
Perilla acetate	HMDB
[4-(Prop-1-en-2-yl)cyclohex-1-en-1-yl]methyl acetic acid	Generator

Chemical Formula

C₁₂H₁₈O₂

Average Molecular Weight

194.2701

Monoisotopic Molecular Weight

194.13067982

IUPAC Name

[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methyl acetate

Traditional Name

[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methyl acetate

CAS Registry Number

15111-96-3

SMILES

CC(=O)OCC1=CCC(CC1)C(C)=C

InChI Identifier

InChI=1S/C12H18O2/c1-9(2)12-6-4-11(5-7-12)8-14-10(3)13/h4,12H,1,5-8H2,2-3H3

InChI Key

WTXBCFKGCNWPLS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037231)

Source

Endogenous

Endogenous (HMDB: HMDB0037231)

Plant

Plant (HMDB: HMDB0037231)

Animal

Animal (HMDB: HMDB0037231)

Exogenous

Food

Food (HMDB: HMDB0037231)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Fruit

Citrus

Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037231)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037231)

Cellular process

Cell signaling (HMDB: HMDB0037231)

Biochemical process

Lipid transport (HMDB: HMDB0037231)

Role

Biological role

Energy storage (HMDB: HMDB0037231)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037231)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037231)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	218.00 to 223.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	3.610 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	3.63	ALOGPS
logP	2.38	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.41 m³·mol⁻¹	ChemAxon
Polarizability	22.39 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	147.745	31661259
DarkChem	[M-H]-	143.225	31661259
DeepCCS	[M+H]+	141.896	30932474
DeepCCS	[M-H]-	139.252	30932474
DeepCCS	[M-2H]-	175.016	30932474
DeepCCS	[M+Na]+	150.554	30932474
AllCCS	[M+H]+	144.8	32859911
AllCCS	[M+H-H2O]+	140.8	32859911
AllCCS	[M+NH4]+	148.6	32859911
AllCCS	[M+Na]+	149.7	32859911
AllCCS	[M-H]-	149.1	32859911
AllCCS	[M+Na-2H]-	150.1	32859911
AllCCS	[M+HCOO]-	151.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Perillyl acetate	CC(=O)OCC1=CCC(CC1)C(C)=C	1834.7	Standard polar	33892256
Perillyl acetate	CC(=O)OCC1=CCC(CC1)C(C)=C	1413.9	Standard non polar	33892256
Perillyl acetate	CC(=O)OCC1=CCC(CC1)C(C)=C	1452.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Perillyl acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-442b31e2dc1c386b2c80	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perillyl acetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9400000000-93d3eaaf9951a78f2711	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 10V, Positive-QTOF	splash10-000b-1900000000-b191393adb7d6521ded0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 20V, Positive-QTOF	splash10-000i-3900000000-1307c45ae24e11447187	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 40V, Positive-QTOF	splash10-0gbc-9200000000-a6c963bb131e06865c6d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 10V, Negative-QTOF	splash10-0006-3900000000-2bf01d0e16bbcd21ecd9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 20V, Negative-QTOF	splash10-052f-9800000000-fb08d476359f0347e338	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 40V, Negative-QTOF	splash10-052f-9600000000-9c74270b55d346720b80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 10V, Negative-QTOF	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 20V, Negative-QTOF	splash10-0a59-9400000000-4c01f51d5d608ecff225	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 40V, Negative-QTOF	splash10-0a4i-9000000000-786c8b3bff2457643571	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 10V, Positive-QTOF	splash10-000b-4900000000-e45fe23e1fc1686118fa	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 20V, Positive-QTOF	splash10-0006-9300000000-936cfd26bff1f5a7cd0a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl acetate 40V, Positive-QTOF	splash10-0006-9200000000-e7b75605b3853fc70071	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016238

KNApSAcK ID

Not Available

Chemspider ID

55667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61780

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1031171

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Perillyl acetate (HMDB0037231)

MOL for HMDB0037231 (Perillyl acetate)

3D MOL for HMDB0037231 (Perillyl acetate)

3D SDF for HMDB0037231 (Perillyl acetate)

3D-SDF for HMDB0037231 (Perillyl acetate)

PDB for HMDB0037231 (Perillyl acetate)

3D PDB for HMDB0037231 (Perillyl acetate)

SMILES for HMDB0037231 (Perillyl acetate)

INCHI for HMDB0037231 (Perillyl acetate)

Structure for HMDB0037231 (Perillyl acetate)

3D Structure for HMDB0037231 (Perillyl acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra