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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:18:51 UTC

Update Date

2021-09-23 20:18:51 UTC

HMDB ID

HMDB0302743

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-Neomenthyl acetate

Description

(+)-neomenthyl 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 (+)-neomenthyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-neomenthyl acetate can be found in orange mint and peppermint, which makes (+)-neomenthyl acetate a potential biomarker for the consumption of these food products.

Structure

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

HMDB0302743
     RDKit          3D
(+)-Neomenthyl acetate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -2.7339    2.9058    0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6069    2.0768    0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    2.4401    1.9479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    0.9083    0.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0981    0.1562    0.8751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7132   -1.2122    1.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872   -1.6946   -0.0609 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0537   -3.0233    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992   -1.8221   -1.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -0.4538   -1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520   -0.1119   -0.1806 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9451    0.9965   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617    0.6595   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7177    1.1338    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911    2.5974   -0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4010    3.9619    0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5799    2.7931    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.6345    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5053   -1.0505    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0515   -1.9232    1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1651   -0.9543   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -2.9440    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427   -3.4343   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944   -3.7516    0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9096   -2.2079   -2.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4208   -2.4800   -0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6413    0.2582   -1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541   -0.4393   -2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -1.0266    0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4935    1.9610   -0.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8177    1.3821   -1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508    0.7034   -2.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4027   -0.3470   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6648    1.6759    0.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277    1.5475    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9977    0.0846    1.2778 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  6
  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 02241221382D          

 14 14  0  0  0  0            999 V2000
   -0.3466   -0.6120    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0549   -0.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398    0.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163    1.0398    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3025    1.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    0.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3755   -0.2132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0825   -0.6369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0825   -1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3617   -1.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3452   -1.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035   -0.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5111   -0.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8170    0.5886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 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>
HMDB0302743

> <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-USWWRNFRSA-N

> <FORMULA>
C12H22O2

> <MOLECULAR_WEIGHT>
198.3019

> <EXACT_MASS>
198.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.664452082478167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,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>
56.59680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
neomenthyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302743
     RDKit          3D
(+)-Neomenthyl acetate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -2.7339    2.9058    0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6069    2.0768    0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    2.4401    1.9479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    0.9083    0.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0981    0.1562    0.8751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7132   -1.2122    1.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872   -1.6946   -0.0609 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0537   -3.0233    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992   -1.8221   -1.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -0.4538   -1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520   -0.1119   -0.1806 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9451    0.9965   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617    0.6595   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7177    1.1338    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911    2.5974   -0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4010    3.9619    0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5799    2.7931    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.6345    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5053   -1.0505    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0515   -1.9232    1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1651   -0.9543   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -2.9440    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427   -3.4343   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944   -3.7516    0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9096   -2.2079   -2.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4208   -2.4800   -0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6413    0.2582   -1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541   -0.4393   -2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -1.0266    0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4935    1.9610   -0.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8177    1.3821   -1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508    0.7034   -2.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4027   -0.3470   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6648    1.6759    0.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277    1.5475    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9977    0.0846    1.2778 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  6
  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      -0.647  -1.142   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.969  -0.352   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.941   1.191   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.590   1.941   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.565   3.476   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.729   1.147   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.701  -0.398   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.021  -1.189   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.021  -3.430   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.675  -2.683   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.644  -3.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.367  -0.441   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.687  -1.233   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.392   1.099   0.000  0.00  0.00           O+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    1    6    8                                                  
CONECT    8    7   12                                                       
CONECT    9   10                                                            
CONECT   10    1    9   11                                                  
CONECT   11   10                                                            
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    HMDB0302743
HETATM    1  C1  UNL     1      -2.734   2.906   0.380  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.607   2.077   0.910  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.993   2.440   1.948  1.00  0.00           O  
HETATM    4  O2  UNL     1      -1.188   0.908   0.317  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.098   0.156   0.875  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.713  -1.212   1.189  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.387  -1.695  -0.061  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.054  -3.023   0.108  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.399  -1.822  -1.206  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.224  -0.454  -1.439  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.952  -0.112  -0.181  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.945   0.996  -0.323  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.962   0.659  -1.394  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.718   1.134   0.974  1.00  0.00           C  
HETATM   15  H1  UNL     1      -2.991   2.597  -0.643  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.401   3.962   0.415  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.580   2.793   1.070  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.302   0.634   1.773  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.505  -1.051   1.952  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.051  -1.923   1.559  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.165  -0.954  -0.330  1.00  0.00           H  
HETATM   22  H8  UNL     1      -3.013  -2.944   0.654  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.243  -3.434  -0.916  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.394  -3.752   0.629  1.00  0.00           H  
HETATM   25  H11 UNL     1      -0.910  -2.208  -2.092  1.00  0.00           H  
HETATM   26  H12 UNL     1       0.421  -2.480  -0.863  1.00  0.00           H  
HETATM   27  H13 UNL     1      -0.641   0.258  -1.536  1.00  0.00           H  
HETATM   28  H14 UNL     1       0.854  -0.439  -2.346  1.00  0.00           H  
HETATM   29  H15 UNL     1       1.533  -1.027   0.137  1.00  0.00           H  
HETATM   30  H16 UNL     1       1.493   1.961  -0.589  1.00  0.00           H  
HETATM   31  H17 UNL     1       3.818   1.382  -1.256  1.00  0.00           H  
HETATM   32  H18 UNL     1       2.551   0.703  -2.412  1.00  0.00           H  
HETATM   33  H19 UNL     1       3.403  -0.347  -1.159  1.00  0.00           H  
HETATM   34  H20 UNL     1       3.665   1.676   0.783  1.00  0.00           H  
HETATM   35  H21 UNL     1       2.128   1.548   1.794  1.00  0.00           H  
HETATM   36  H22 UNL     1       2.998   0.085   1.278  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

HMDB0302743
     RDKit          3D
(+)-Neomenthyl acetate
 36 36  0  0  0  0  0  0  0  0999 V2000
   -2.7339    2.9058    0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6069    2.0768    0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    2.4401    1.9479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    0.9083    0.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0981    0.1562    0.8751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7132   -1.2122    1.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872   -1.6946   -0.0609 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0537   -3.0233    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992   -1.8221   -1.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -0.4538   -1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520   -0.1119   -0.1806 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9451    0.9965   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617    0.6595   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7177    1.1338    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911    2.5974   -0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4010    3.9619    0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5799    2.7931    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.6345    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5053   -1.0505    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0515   -1.9232    1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1651   -0.9543   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -2.9440    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427   -3.4343   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944   -3.7516    0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9096   -2.2079   -2.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4208   -2.4800   -0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6413    0.2582   -1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541   -0.4393   -2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5329   -1.0266    0.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4935    1.9610   -0.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8177    1.3821   -1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508    0.7034   -2.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4027   -0.3470   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6648    1.6759    0.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277    1.5475    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9977    0.0846    1.2778 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  6
  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
Neomenthyl acetic acid	Generator
(+)-Neomenthyl acetic acid	Generator

Chemical Formula

C₁₂H₂₂O₂

Average Molecular Weight

198.3019

Monoisotopic Molecular Weight

198.161979948

IUPAC Name

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

Traditional Name

neomenthyl 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-USWWRNFRSA-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

p-menthane monoterpenoid (CHEBI:80758 )
Cyclic monoterpenes (C16825 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302743)

Food

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)
Orange mint (FooDB: FOOD00110)

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	23.66 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]+	153.364	30932474
DeepCCS	[M-H]-	151.006	30932474
DeepCCS	[M-2H]-	183.982	30932474
DeepCCS	[M+Na]+	159.457	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	18.5771 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.23 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2508.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	617.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	226.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	356.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	835.1 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	805.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	88.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1509.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	545.5 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	1679.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	481.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	447.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	492.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	542.6 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	11.9 seconds	40023050

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 - (+)-Neomenthyl acetate 10V, Positive-QTOF	splash10-0002-1900000000-d72c827a469085629e5d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Neomenthyl acetate 20V, Positive-QTOF	splash10-0a4s-4900000000-bf6fb3a5690a1f032087	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Neomenthyl acetate 40V, Positive-QTOF	splash10-0aor-9200000000-cb81ded288f2424a3556	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Neomenthyl acetate 10V, Negative-QTOF	splash10-052b-0900000000-3501f1a47f8406c0d6f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Neomenthyl acetate 20V, Negative-QTOF	splash10-0a4i-2900000000-cb66f3b5eaa6461df117	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Neomenthyl acetate 40V, Negative-QTOF	splash10-0a4r-4900000000-dcd4936d192617ff7768	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Neomenthyl acetate 10V, Positive-QTOF	splash10-0002-9300000000-262f2d6c6ac2e6185671	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Neomenthyl acetate 20V, Positive-QTOF	splash10-0012-9300000000-24944363b89e43dd9c2b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Neomenthyl acetate 40V, Positive-QTOF	splash10-0006-9000000000-4f2ea1271e666be87dda	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Neomenthyl acetate 10V, Negative-QTOF	splash10-052b-2900000000-6b5ecc1c9ffb6ea43737	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Neomenthyl acetate 20V, Negative-QTOF	splash10-0a4i-9500000000-d0a742a52154626c4906	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Neomenthyl 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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75699

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 (+)-Neomenthyl acetate (HMDB0302743)

MOL for HMDB0302743 ((+)-Neomenthyl acetate)

3D MOL for HMDB0302743 ((+)-Neomenthyl acetate)

3D SDF for HMDB0302743 ((+)-Neomenthyl acetate)

3D-SDF for HMDB0302743 ((+)-Neomenthyl acetate)

PDB for HMDB0302743 ((+)-Neomenthyl acetate)

3D PDB for HMDB0302743 ((+)-Neomenthyl acetate)

SMILES for HMDB0302743 ((+)-Neomenthyl acetate)

INCHI for HMDB0302743 ((+)-Neomenthyl acetate)

Structure for HMDB0302743 ((+)-Neomenthyl acetate)

3D Structure for HMDB0302743 ((+)-Neomenthyl acetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra