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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:33:21 UTC

Update Date

2021-09-23 20:33:21 UTC

HMDB ID

HMDB0302770

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Neoisomenthol acetate

Description

Neoisomenthol acetate is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids 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. Neoisomenthol acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Neoisomenthol acetate can be found in peppermint, which makes neoisomenthol acetate a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302770
     RDKit          3D
Neoisomenthol acetate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -0.9440    4.1255    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    2.8749    0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486    2.8994    1.7069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    1.7134   -0.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3756    0.5794    0.3061 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4046    0.1981   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -0.8460   -0.0483 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5784   -1.0618   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4165   -2.0691    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -1.8581    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5140   -0.5788    0.6507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6501   -0.6988   -0.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5601   -1.8590   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117    0.5469   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3555    4.5324    1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7371    3.9759   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950    4.8662    0.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918    0.7847    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9238   -0.3034   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9742    1.0921   -1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4357   -0.4842    1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398   -0.3923   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779   -2.1338   -1.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4338   -0.9173    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0234   -2.8851    0.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582   -2.3830   -0.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5336   -1.9872    1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686   -2.7362    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0165   -0.3048    1.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819   -0.8430   -1.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5313   -1.6410   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2054   -2.8166   -0.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -1.9160    1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2752    1.1853   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5953    0.2641   -0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856    1.0771    0.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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  1  0
 11  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
  7 21  1  1
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  1
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END


  Mrv0541 02241222492D          

 14 14  0  0  0  0            999 V2000
    0.8839    0.3241    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1695   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1695   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -1.3259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5984   -0.9134    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5984   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3129   -1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984   -2.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1695   -2.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0274   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7418   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0273   -0.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  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  7  1  1  0  0  0
  5  8  1  1  0  0  0
  4  9  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  1  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>
HMDB0302770

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3/t9-,11-,12-/m1/s1

> <INCHI_KEY>
XHXUANMFYXWVNG-YUSALJHKSA-N

> <FORMULA>
C12H22O2

> <MOLECULAR_WEIGHT>
198.3019

> <EXACT_MASS>
198.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.588225840881737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexyl acetate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
3.1053985573333325

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.003223453074533

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
56.5968

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R)-2-isopropyl-5-methylcyclohexyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302770
     RDKit          3D
Neoisomenthol acetate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -0.9440    4.1255    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    2.8749    0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486    2.8994    1.7069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    1.7134   -0.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3756    0.5794    0.3061 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4046    0.1981   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -0.8460   -0.0483 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5784   -1.0618   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4165   -2.0691    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -1.8581    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5140   -0.5788    0.6507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6501   -0.6988   -0.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5601   -1.8590   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117    0.5469   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3555    4.5324    1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7371    3.9759   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950    4.8662    0.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918    0.7847    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9238   -0.3034   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9742    1.0921   -1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4357   -0.4842    1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398   -0.3923   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779   -2.1338   -1.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4338   -0.9173    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0234   -2.8851    0.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582   -2.3830   -0.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5336   -1.9872    1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686   -2.7362    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0165   -0.3048    1.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819   -0.8430   -1.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5313   -1.6410   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2054   -2.8166   -0.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -1.9160    1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2752    1.1853   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5953    0.2641   -0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856    1.0771    0.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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  1  0
 11  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
  7 21  1  1
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  1
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  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       1.650   0.605   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.316  -0.165   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.316  -1.705   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.650  -2.475   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.984  -1.705   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.984  -0.165   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.650   2.145   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.317  -2.475   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.650  -4.015   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.984  -4.785   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.316  -4.785   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.651  -1.705   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.985  -2.475   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.651  -0.165   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    1    5                                                       
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    HMDB0302770
HETATM    1  C1  UNL     1      -0.944   4.126   0.383  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.212   2.875   0.703  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.549   2.899   1.707  1.00  0.00           O  
HETATM    4  O2  UNL     1      -0.336   1.713  -0.046  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.376   0.579   0.306  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.405   0.198  -0.768  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.271  -0.846  -0.048  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.578  -1.062  -0.705  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.417  -2.069   0.017  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.201  -1.858   0.875  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.514  -0.579   0.651  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.650  -0.699  -0.357  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.560  -1.859  -0.034  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.512   0.547  -0.355  1.00  0.00           C  
HETATM   15  H1  UNL     1      -1.356   4.532   1.340  1.00  0.00           H  
HETATM   16  H2  UNL     1      -1.737   3.976  -0.374  1.00  0.00           H  
HETATM   17  H3  UNL     1      -0.195   4.866   0.033  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.992   0.785   1.213  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.924  -0.303  -1.624  1.00  0.00           H  
HETATM   20  H6  UNL     1       1.974   1.092  -1.014  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.436  -0.484   1.006  1.00  0.00           H  
HETATM   22  H8  UNL     1       3.740  -0.392  -1.572  1.00  0.00           H  
HETATM   23  H9  UNL     1       3.678  -2.134  -1.032  1.00  0.00           H  
HETATM   24  H10 UNL     1       4.434  -0.917   0.012  1.00  0.00           H  
HETATM   25  H11 UNL     1       2.023  -2.885   0.479  1.00  0.00           H  
HETATM   26  H12 UNL     1       1.158  -2.383  -0.997  1.00  0.00           H  
HETATM   27  H13 UNL     1       0.534  -1.987   1.935  1.00  0.00           H  
HETATM   28  H14 UNL     1      -0.469  -2.736   0.681  1.00  0.00           H  
HETATM   29  H15 UNL     1      -1.017  -0.305   1.610  1.00  0.00           H  
HETATM   30  H16 UNL     1      -1.282  -0.843  -1.386  1.00  0.00           H  
HETATM   31  H17 UNL     1      -3.531  -1.641  -0.554  1.00  0.00           H  
HETATM   32  H18 UNL     1      -2.205  -2.817  -0.445  1.00  0.00           H  
HETATM   33  H19 UNL     1      -2.813  -1.916   1.045  1.00  0.00           H  
HETATM   34  H20 UNL     1      -2.275   1.185  -1.230  1.00  0.00           H  
HETATM   35  H21 UNL     1      -3.595   0.264  -0.505  1.00  0.00           H  
HETATM   36  H22 UNL     1      -2.486   1.077   0.609  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   11   18
CONECT    6    7   19   20
CONECT    7    8    9   21
CONECT    8   22   23   24
CONECT    9   10   25   26
CONECT   10   11   27   28
CONECT   11   12   29
CONECT   12   13   14   30
CONECT   13   31   32   33
CONECT   14   34   35   36
END

HMDB0302770
     RDKit          3D
Neoisomenthol acetate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -0.9440    4.1255    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    2.8749    0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486    2.8994    1.7069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    1.7134   -0.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3756    0.5794    0.3061 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4046    0.1981   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -0.8460   -0.0483 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5784   -1.0618   -0.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4165   -2.0691    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -1.8581    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5140   -0.5788    0.6507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6501   -0.6988   -0.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5601   -1.8590   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117    0.5469   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3555    4.5324    1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7371    3.9759   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950    4.8662    0.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918    0.7847    1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9238   -0.3034   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9742    1.0921   -1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4357   -0.4842    1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398   -0.3923   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6779   -2.1338   -1.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4338   -0.9173    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0234   -2.8851    0.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1582   -2.3830   -0.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5336   -1.9872    1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686   -2.7362    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0165   -0.3048    1.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819   -0.8430   -1.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5313   -1.6410   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2054   -2.8166   -0.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -1.9160    1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2752    1.1853   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5953    0.2641   -0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856    1.0771    0.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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  1  0
 11  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
  7 21  1  1
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  1
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1R,2R,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl acetic acid	Generator
Neoisomenthol acetic acid	Generator

Chemical Formula

C₁₂H₂₂O₂

Average Molecular Weight

198.3019

Monoisotopic Molecular Weight

198.161979948

IUPAC Name

(1R,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexyl acetate

Traditional Name

(1R,2R,5R)-2-isopropyl-5-methylcyclohexyl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3/t9-,11-,12-/m1/s1

InChI Key

XHXUANMFYXWVNG-YUSALJHKSA-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

Not Available

Peppermint (FooDB: FOOD00113)

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
logP	3.54	ALOGPS
logP	3.11	ChemAxon
logS	-4	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	56.6 m³·mol⁻¹	ChemAxon
Polarizability	23.59 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
AllCCS	[M+H]+	146.148	32859911
AllCCS	[M+H-H2O]+	142.208	32859911
AllCCS	[M+Na]+	150.87	32859911
AllCCS	[M+NH4]+	149.814	32859911
AllCCS	[M-H]-	151.369	32859911
AllCCS	[M+Na-2H]-	152.479	32859911
AllCCS	[M+HCOO]-	153.79	32859911
DeepCCS	[M+H]+	151.674	30932474
DeepCCS	[M-H]-	149.317	30932474
DeepCCS	[M-2H]-	182.389	30932474
DeepCCS	[M+Na]+	157.768	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 10V, Positive-QTOF	splash10-0002-1900000000-d72c827a469085629e5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 20V, Positive-QTOF	splash10-0a4s-4900000000-bf6fb3a5690a1f032087	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 40V, Positive-QTOF	splash10-0aor-9200000000-cb81ded288f2424a3556	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 10V, Negative-QTOF	splash10-052b-0900000000-3501f1a47f8406c0d6f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 20V, Negative-QTOF	splash10-0a4i-2900000000-cb66f3b5eaa6461df117	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 40V, Negative-QTOF	splash10-0a4r-4900000000-dcd4936d192617ff7768	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 10V, Positive-QTOF	splash10-0002-9300000000-262f2d6c6ac2e6185671	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 20V, Positive-QTOF	splash10-0012-9300000000-24944363b89e43dd9c2b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 40V, Positive-QTOF	splash10-0006-9000000000-4f2ea1271e666be87dda	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 10V, Negative-QTOF	splash10-052b-2900000000-6b5ecc1c9ffb6ea43737	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 20V, Negative-QTOF	splash10-0a4i-9500000000-d0a742a52154626c4906	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neoisomenthol acetate 40V, Negative-QTOF	splash10-0a4l-9000000000-a08bf949a70eb12bd609	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB006176

KNApSAcK ID

Not Available

Chemspider ID

80028

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for Neoisomenthol acetate (HMDB0302770)

MOL for HMDB0302770 (Neoisomenthol acetate)

3D MOL for HMDB0302770 (Neoisomenthol acetate)

3D SDF for HMDB0302770 (Neoisomenthol acetate)

3D-SDF for HMDB0302770 (Neoisomenthol acetate)

PDB for HMDB0302770 (Neoisomenthol acetate)

3D PDB for HMDB0302770 (Neoisomenthol acetate)

SMILES for HMDB0302770 (Neoisomenthol acetate)

INCHI for HMDB0302770 (Neoisomenthol acetate)

Structure for HMDB0302770 (Neoisomenthol acetate)

3D Structure for HMDB0302770 (Neoisomenthol acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra