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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:45:51 UTC

Update Date

2023-02-21 17:27:59 UTC

HMDB ID

HMDB0040227

Secondary Accession Numbers

HMDB40227

Metabolite Identification

Common Name

Isopulegol acetate

Description

Isopulegol 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 small amount of articles have been published on Isopulegol acetate.

Structure

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

HMDB0040227
     RDKit          3D
Isopulegol acetate
 34 34  0  0  0  0  0  0  0  0999 V2000
    2.4049   -1.1861   -1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0013   -0.4557   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8392    0.6830    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7479   -0.7613    0.2660 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0446   -1.9575   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270   -2.2873    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -1.1056    0.4688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4118   -1.3600    1.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3581    0.0060    1.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2504    0.3895    0.2095 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3124    1.6265    0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857    2.6335   -0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734    3.9884   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560    2.3878   -1.5604 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624   -2.0354   -1.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3365   -0.9421   -1.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5358    1.1124    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926    0.3065    0.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9111    1.4499   -0.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172   -1.0260    1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -2.8352   -0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1977   -1.7151   -1.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -3.0628   -0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9658   -2.7213    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241   -0.7480   -0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2369   -1.5603    2.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0253   -0.4347    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9921   -2.1444    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9916    0.8471    1.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -0.4862    2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6930    0.3430   -0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    4.0080   -0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3644    4.7020   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200    4.3417    0.8071 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 10  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  1
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  6
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  6
 13 32  1  0
 13 33  1  0
 13 34  1  0
M  END


  Mrv0541 02241220172D          

 14 14  0  0  0  0            999 V2000
   -3.3295   -3.7419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0439   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -5.3920    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6150   -4.9795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6150   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -2.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9005   -5.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -6.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150   -6.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439   -6.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1860   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4716   -5.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1861   -4.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  1  0  0  0
  5  8  1  1  0  0  0
  4  9  1  6  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040227

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1CC[C@H]([C@@H](C1)OC(C)=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h9,11-12H,1,5-7H2,2-4H3/t9-,11+,12-/m1/s1

> <INCHI_KEY>
HLHIVJRLODSUCI-ADEWGFFLSA-N

> <FORMULA>
C12H20O2

> <MOLECULAR_WEIGHT>
196.286

> <EXACT_MASS>
196.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.97532770007743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
2.757752746333333

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.003905547444444

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
56.3743

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0040227
     RDKit          3D
Isopulegol acetate
 34 34  0  0  0  0  0  0  0  0999 V2000
    2.4049   -1.1861   -1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0013   -0.4557   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8392    0.6830    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7479   -0.7613    0.2660 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0446   -1.9575   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270   -2.2873    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -1.1056    0.4688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4118   -1.3600    1.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3581    0.0060    1.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2504    0.3895    0.2095 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3124    1.6265    0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857    2.6335   -0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734    3.9884   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560    2.3878   -1.5604 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624   -2.0354   -1.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3365   -0.9421   -1.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5358    1.1124    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926    0.3065    0.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9111    1.4499   -0.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172   -1.0260    1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -2.8352   -0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1977   -1.7151   -1.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -3.0628   -0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9658   -2.7213    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241   -0.7480   -0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2369   -1.5603    2.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0253   -0.4347    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9921   -2.1444    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9916    0.8471    1.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -0.4862    2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6930    0.3430   -0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    4.0080   -0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3644    4.7020   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200    4.3417    0.8071 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 10  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  1
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  6
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  6
 13 32  1  0
 13 33  1  0
 13 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.215  -6.985   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.549  -7.755   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.549  -9.295   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.215 -10.065   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.881  -9.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.881  -7.755   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.215  -5.445   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.548 -10.065   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.215 -11.605   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.881 -12.375   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.549 -12.375   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.214  -9.295   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.880 -10.065   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.214  -7.755   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1                                                       
CONECT    7    1                                                            
CONECT    8    5   12                                                       
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0040227
HETATM    1  C1  UNL     1       2.405  -1.186  -1.431  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.001  -0.456  -0.415  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.839   0.683   0.031  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.748  -0.761   0.266  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.045  -1.958  -0.339  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.227  -2.287   0.384  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.133  -1.106   0.469  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.412  -1.360   1.178  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.358   0.006   1.176  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.250   0.389   0.210  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.312   1.626   0.493  1.00  0.00           O  
HETATM   12  C11 UNL     1       0.286   2.633  -0.458  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.873   3.988  -0.217  1.00  0.00           C  
HETATM   14  O2  UNL     1      -0.256   2.388  -1.560  1.00  0.00           O  
HETATM   15  H1  UNL     1       1.862  -2.035  -1.828  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.336  -0.942  -1.919  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.536   1.112   0.993  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.893   0.307   0.190  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.911   1.450  -0.790  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.917  -1.026   1.352  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.726  -2.835  -0.347  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.198  -1.715  -1.393  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.757  -3.063  -0.241  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.966  -2.721   1.365  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.324  -0.748  -0.564  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.237  -1.560   2.254  1.00  0.00           H  
HETATM   27  H13 UNL     1      -4.025  -0.435   1.134  1.00  0.00           H  
HETATM   28  H14 UNL     1      -3.992  -2.144   0.669  1.00  0.00           H  
HETATM   29  H15 UNL     1      -1.992   0.847   1.460  1.00  0.00           H  
HETATM   30  H16 UNL     1      -0.912  -0.486   2.089  1.00  0.00           H  
HETATM   31  H17 UNL     1      -0.693   0.343  -0.829  1.00  0.00           H  
HETATM   32  H18 UNL     1       1.957   4.008  -0.526  1.00  0.00           H  
HETATM   33  H19 UNL     1       0.364   4.702  -0.897  1.00  0.00           H  
HETATM   34  H20 UNL     1       0.720   4.342   0.807  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3    4
CONECT    3   17   18   19
CONECT    4    5   10   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8    9   25
CONECT    8   26   27   28
CONECT    9   10   29   30
CONECT   10   11   31
CONECT   11   12
CONECT   12   13   14   14
CONECT   13   32   33   34
END

HMDB0040227
     RDKit          3D
Isopulegol acetate
 34 34  0  0  0  0  0  0  0  0999 V2000
    2.4049   -1.1861   -1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0013   -0.4557   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8392    0.6830    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7479   -0.7613    0.2660 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0446   -1.9575   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270   -2.2873    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1332   -1.1056    0.4688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4118   -1.3600    1.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3581    0.0060    1.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2504    0.3895    0.2095 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3124    1.6265    0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2857    2.6335   -0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734    3.9884   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560    2.3878   -1.5604 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624   -2.0354   -1.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3365   -0.9421   -1.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5358    1.1124    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926    0.3065    0.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9111    1.4499   -0.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172   -1.0260    1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -2.8352   -0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1977   -1.7151   -1.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -3.0628   -0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9658   -2.7213    1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3241   -0.7480   -0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2369   -1.5603    2.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0253   -0.4347    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9921   -2.1444    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9916    0.8471    1.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -0.4862    2.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6930    0.3430   -0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    4.0080   -0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3644    4.7020   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200    4.3417    0.8071 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 10  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  1
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  6
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  6
 13 32  1  0
 13 33  1  0
 13 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isopulegol acetic acid	Generator
1-Methyl-4-isopropenylcyclohexan-3-yl acetate	HMDB
2-Isopropenyl-5-methylcyclohexyl acetate	HMDB
5-Methyl-2-(1-methylethenyl)cyclohexanol acetate	HMDB
Cyclohexanol, 5-methyl-2-(1-methylethenyl), acetate	HMDB
FEMA 2965	HMDB
Isopropenylcyclohexan-3-ol acetate	HMDB
Isopulegolacetate	HMDB
Isopulegyl acetate	HMDB
P-Menth-8-en-3-yl acetate	HMDB
(1R,2S,5R)-5-Methyl-2-(prop-1-en-2-yl)cyclohexyl acetic acid	Generator
(-)-Isopulegol acetic acid	Generator

Chemical Formula

C₁₂H₂₀O₂

Average Molecular Weight

196.286

Monoisotopic Molecular Weight

196.146329884

IUPAC Name

(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate

Traditional Name

(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate

CAS Registry Number

89-49-6

SMILES

C[C@@H]1CC[C@H]([C@@H](C1)OC(C)=O)C(C)=C

InChI Identifier

InChI=1S/C12H20O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h9,11-12H,1,5-7H2,2-4H3/t9-,11+,12-/m1/s1

InChI Key

HLHIVJRLODSUCI-ADEWGFFLSA-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

Sweet

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040227)

Source

Endogenous

Endogenous (HMDB: HMDB0040227)

Plant

Plant (HMDB: HMDB0040227)

Animal

Animal (HMDB: HMDB0040227)

Exogenous

Food

Food (HMDB: HMDB0040227)

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040227)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040227)

Cellular process

Cell signaling (HMDB: HMDB0040227)

Biochemical process

Lipid transport (HMDB: HMDB0040227)

Role

Biological role

Energy storage (HMDB: HMDB0040227)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040227)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040227)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	657.95 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.49 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.930 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.49	ALOGPS
logP	2.76	ChemAxon
logS	-3.1	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	3	ChemAxon
Refractivity	56.37 m³·mol⁻¹	ChemAxon
Polarizability	22.98 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]+	146.285	31661259
DarkChem	[M-H]-	146.196	31661259
DeepCCS	[M+H]+	150.277	30932474
DeepCCS	[M-H]-	147.881	30932474
DeepCCS	[M-2H]-	181.139	30932474
DeepCCS	[M+Na]+	156.224	30932474
AllCCS	[M+H]+	145.3	32859911
AllCCS	[M+H-H2O]+	141.3	32859911
AllCCS	[M+NH4]+	149.0	32859911
AllCCS	[M+Na]+	150.1	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
Isopulegol acetate	C[C@@H]1CC[C@H]([C@@H](C1)OC(C)=O)C(C)=C	1653.8	Standard polar	33892256
Isopulegol acetate	C[C@@H]1CC[C@H]([C@@H](C1)OC(C)=O)C(C)=C	1324.0	Standard non polar	33892256
Isopulegol acetate	C[C@@H]1CC[C@H]([C@@H](C1)OC(C)=O)C(C)=C	1298.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isopulegol acetate EI-B (Non-derivatized)	splash10-0006-9300000000-cba940c1d1f1aaf19f8e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopulegol acetate EI-B (Non-derivatized)	splash10-000f-9700000000-2ac8659513735c5f1608	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopulegol acetate EI-B (Non-derivatized)	splash10-0006-9300000000-cba940c1d1f1aaf19f8e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopulegol acetate EI-B (Non-derivatized)	splash10-000f-9700000000-2ac8659513735c5f1608	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopulegol acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9400000000-782001fc756db8f2ed3e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopulegol acetate 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 - Isopulegol acetate 10V, Positive-QTOF	splash10-0002-0900000000-c310b45afbf8bebec140	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegol acetate 20V, Positive-QTOF	splash10-0a4s-5900000000-74e3c99e5e97bce0a7aa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegol acetate 40V, Positive-QTOF	splash10-0aor-9100000000-7b358df4198c2d161d6c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegol acetate 10V, Negative-QTOF	splash10-0f6t-0900000000-a51ca72efa8995b84a7d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegol acetate 20V, Negative-QTOF	splash10-0udj-2900000000-5a26b25a09d1449267f5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegol acetate 40V, Negative-QTOF	splash10-0m53-5900000000-6e0fbbcee54aa6be4254	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegol acetate 10V, Positive-QTOF	splash10-0002-9500000000-93096a7d46cef7b4b612	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegol acetate 20V, Positive-QTOF	splash10-001m-9400000000-3834eca8ad8d46f748bc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegol acetate 40V, Positive-QTOF	splash10-00kf-9000000000-16c4be2637c6fc12fd2c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegol acetate 10V, Negative-QTOF	splash10-0a4i-9500000000-01f5d7361d665b4a2f29	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegol acetate 20V, Negative-QTOF	splash10-0a4i-9200000000-c7e76a2ea7308d0c72da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegol acetate 40V, Negative-QTOF	splash10-0a4l-9000000000-4be60751d3ccfe7fd79a	2021-09-24	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

FDB019941

KNApSAcK ID

Not Available

Chemspider ID

85346

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94579

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1427131

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 Isopulegol acetate (HMDB0040227)

MOL for HMDB0040227 (Isopulegol acetate)

3D MOL for HMDB0040227 (Isopulegol acetate)

3D SDF for HMDB0040227 (Isopulegol acetate)

3D-SDF for HMDB0040227 (Isopulegol acetate)

PDB for HMDB0040227 (Isopulegol acetate)

3D PDB for HMDB0040227 (Isopulegol acetate)

SMILES for HMDB0040227 (Isopulegol acetate)

INCHI for HMDB0040227 (Isopulegol acetate)

Structure for HMDB0040227 (Isopulegol acetate)

3D Structure for HMDB0040227 (Isopulegol acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra