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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 03:07:21 UTC

Update Date

2021-09-24 03:07:21 UTC

HMDB ID

HMDB0303595

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(R)-Menthone 8-thioacetate

Description

(2R,5S)-2-[2-(acetylsulfanyl)propan-2-yl]-5-methylcyclohexan-1-one 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 very few articles have been published on (2R,5S)-2-[2-(acetylsulfanyl)propan-2-yl]-5-methylcyclohexan-1-one.

Structure

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

HMDB0303595
     RDKit          3D
(R)-Menthone 8-thioacetate
 35 35  0  0  0  0  0  0  0  0999 V2000
    5.0722    1.3268   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9765    0.3710    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297   -0.7996    0.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2969    0.9383    0.0945 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -0.3743    0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442   -1.3432   -0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074   -1.1114    1.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    0.1785    0.6513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2762   -0.9108    0.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -0.4462    1.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676    0.6215    0.2390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9080    0.0610   -0.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344    1.5726   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065    0.9787   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    1.1387   -1.4592 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7640    2.3823   -0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9387    1.1683    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3964    1.2420   -1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2068   -1.3499   -1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -1.0969   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642   -2.3737   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5800   -1.2014    1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932   -0.6273    2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0386   -2.1343    1.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2386    0.7989    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2409   -1.7045    0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328   -1.4341    1.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884   -0.1407    2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435   -1.3315    1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255    1.2240    0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8439   -0.4304   -0.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -0.6156   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1893    0.9570   -1.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0277    2.4077    0.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237    2.0584   -1.2069 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
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
M  END


  Mrv0541 10241203472D          

 15 15  0  0  0  0            999 V2000
   -1.2670   -4.7437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9814   -5.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814   -5.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -6.3938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5525   -5.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5525   -5.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -3.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620   -6.3938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -7.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5525   -7.6313    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814   -7.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -8.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5525   -8.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620   -8.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -8.8688    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  6  0  0  0
  5  8  2  0  0  0  0
  4  9  1  6  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303595

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O2S/c1-8-5-6-10(11(14)7-8)12(3,4)15-9(2)13/h8,10H,5-7H2,1-4H3/t8-,10+/m0/s1

> <INCHI_KEY>
AMXPURQVAMENCC-WCBMZHEXSA-N

> <FORMULA>
C12H20O2S

> <MOLECULAR_WEIGHT>
228.351

> <EXACT_MASS>
228.118400574

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.50910515540429

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,5S)-2-[2-(acetylsulfanyl)propan-2-yl]-5-methylcyclohexan-1-one

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
2.619001199999999

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.02119369525864

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
63.797000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5S)-2-[2-(acetylsulfanyl)propan-2-yl]-5-methylcyclohexan-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0303595
     RDKit          3D
(R)-Menthone 8-thioacetate
 35 35  0  0  0  0  0  0  0  0999 V2000
    5.0722    1.3268   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9765    0.3710    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297   -0.7996    0.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2969    0.9383    0.0945 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -0.3743    0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442   -1.3432   -0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074   -1.1114    1.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    0.1785    0.6513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2762   -0.9108    0.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -0.4462    1.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676    0.6215    0.2390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9080    0.0610   -0.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344    1.5726   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065    0.9787   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    1.1387   -1.4592 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7640    2.3823   -0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9387    1.1683    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3964    1.2420   -1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2068   -1.3499   -1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -1.0969   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642   -2.3737   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5800   -1.2014    1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932   -0.6273    2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0386   -2.1343    1.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2386    0.7989    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2409   -1.7045    0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328   -1.4341    1.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884   -0.1407    2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435   -1.3315    1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255    1.2240    0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8439   -0.4304   -0.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -0.6156   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1893    0.9570   -1.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0277    2.4077    0.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237    2.0584   -1.2069 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
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
M  END

HEADER    PROTEIN                                 24-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-OCT-12         0                                  
HETATM    1  C   UNK     0      -2.365  -8.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.699  -9.625   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.699 -11.165   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.365 -11.935   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.031 -11.165   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.031  -9.625   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.365  -7.315   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.302 -11.935   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.365 -13.475   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0      -1.031 -14.245   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0      -3.699 -14.245   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.365 -15.015   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.031 -15.785   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.302 -16.555   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.365 -16.555   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                                                            
CONECT    9    4   10   11   12                                             
CONECT   10    9   13                                                       
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0303595
HETATM    1  C1  UNL     1       5.072   1.327  -0.152  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.976   0.371   0.074  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.230  -0.800   0.244  1.00  0.00           O  
HETATM    4  S1  UNL     1       2.297   0.938   0.094  1.00  0.00           S  
HETATM    5  C3  UNL     1       1.096  -0.374   0.421  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.144  -1.343  -0.730  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.507  -1.111   1.673  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.282   0.179   0.651  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.276  -0.911   0.921  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.658  -0.446   1.133  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.168   0.622   0.239  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.908   0.061  -0.983  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.134   1.573  -0.286  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.807   0.979  -0.459  1.00  0.00           C  
HETATM   15  O2  UNL     1      -0.178   1.139  -1.459  1.00  0.00           O  
HETATM   16  H1  UNL     1       4.764   2.382  -0.003  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.939   1.168   0.530  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.396   1.242  -1.201  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.207  -1.350  -1.108  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.488  -1.097  -1.566  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.964  -2.374  -0.331  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.580  -1.201   1.803  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.993  -0.627   2.535  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.039  -2.134   1.592  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.239   0.799   1.595  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.241  -1.704   0.124  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.933  -1.434   1.855  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.788  -0.141   2.213  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.344  -1.331   1.021  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.926   1.224   0.783  1.00  0.00           H  
HETATM   31  H16 UNL     1      -4.844  -0.430  -0.704  1.00  0.00           H  
HETATM   32  H17 UNL     1      -3.228  -0.616  -1.565  1.00  0.00           H  
HETATM   33  H18 UNL     1      -4.189   0.957  -1.606  1.00  0.00           H  
HETATM   34  H19 UNL     1      -2.028   2.408   0.466  1.00  0.00           H  
HETATM   35  H20 UNL     1      -2.524   2.058  -1.207  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    7    8
CONECT    6   19   20   21
CONECT    7   22   23   24
CONECT    8    9   14   25
CONECT    9   10   26   27
CONECT   10   11   28   29
CONECT   11   12   13   30
CONECT   12   31   32   33
CONECT   13   14   34   35
CONECT   14   15   15
END

HMDB0303595
     RDKit          3D
(R)-Menthone 8-thioacetate
 35 35  0  0  0  0  0  0  0  0999 V2000
    5.0722    1.3268   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9765    0.3710    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297   -0.7996    0.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2969    0.9383    0.0945 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -0.3743    0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442   -1.3432   -0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074   -1.1114    1.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2823    0.1785    0.6513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2762   -0.9108    0.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -0.4462    1.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676    0.6215    0.2390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9080    0.0610   -0.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344    1.5726   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065    0.9787   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778    1.1387   -1.4592 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7640    2.3823   -0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9387    1.1683    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3964    1.2420   -1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2068   -1.3499   -1.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -1.0969   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642   -2.3737   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5800   -1.2014    1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9932   -0.6273    2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0386   -2.1343    1.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2386    0.7989    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2409   -1.7045    0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328   -1.4341    1.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884   -0.1407    2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435   -1.3315    1.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255    1.2240    0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8439   -0.4304   -0.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -0.6156   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1893    0.9570   -1.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0277    2.4077    0.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237    2.0584   -1.2069 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
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  1
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R,5S)-2-[2-(Acetylsulphanyl)propan-2-yl]-5-methylcyclohexan-1-one	Generator
(R)-Menthone 8-thioacetic acid	Generator

Chemical Formula

C₁₂H₂₀O₂S

Average Molecular Weight

228.351

Monoisotopic Molecular Weight

228.118400574

IUPAC Name

(2R,5S)-2-[2-(acetylsulfanyl)propan-2-yl]-5-methylcyclohexan-1-one

Traditional Name

(2R,5S)-2-[2-(acetylsulfanyl)propan-2-yl]-5-methylcyclohexan-1-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H20O2S/c1-8-5-6-10(11(14)7-8)12(3,4)15-9(2)13/h8,10H,5-7H2,1-4H3/t8-,10+/m0/s1

InChI Key

AMXPURQVAMENCC-WCBMZHEXSA-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

Monocyclic monoterpenoid
P-menthane monoterpenoid
Ketone
Thiocarboxylic acid ester
Cyclic ketone
Carbothioic s-ester
Sulfenyl compound
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Carbonyl group
Organosulfur compound
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

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	3.27	ALOGPS
logP	2.62	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.8 m³·mol⁻¹	ChemAxon
Polarizability	25.51 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]+	149.793	32859911
AllCCS	[M+H-H2O]+	146.239	32859911
AllCCS	[M+Na]+	154.043	32859911
AllCCS	[M+NH4]+	153.093	32859911
AllCCS	[M-H]-	157.578	32859911
AllCCS	[M+Na-2H]-	158.562	32859911
AllCCS	[M+HCOO]-	159.74	32859911
DeepCCS	[M+H]+	155.847	30932474
DeepCCS	[M-H]-	153.452	30932474
DeepCCS	[M-2H]-	186.413	30932474
DeepCCS	[M+Na]+	161.794	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Menthone 8-thioacetate,1TMS,isomer #1	CC(=O)SC(C)(C)C1=C(O[Si](C)(C)C)C[C@@H](C)CC1	1713.8	Semi standard non polar	33892256
(R)-Menthone 8-thioacetate,1TMS,isomer #1	CC(=O)SC(C)(C)C1=C(O[Si](C)(C)C)C[C@@H](C)CC1	1765.6	Standard non polar	33892256
(R)-Menthone 8-thioacetate,1TMS,isomer #1	CC(=O)SC(C)(C)C1=C(O[Si](C)(C)C)C[C@@H](C)CC1	2038.9	Standard polar	33892256
(R)-Menthone 8-thioacetate,1TMS,isomer #2	CC(=O)SC(C)(C)[C@@H]1CC[C@H](C)C=C1O[Si](C)(C)C	1715.6	Semi standard non polar	33892256
(R)-Menthone 8-thioacetate,1TMS,isomer #2	CC(=O)SC(C)(C)[C@@H]1CC[C@H](C)C=C1O[Si](C)(C)C	1792.4	Standard non polar	33892256
(R)-Menthone 8-thioacetate,1TMS,isomer #2	CC(=O)SC(C)(C)[C@@H]1CC[C@H](C)C=C1O[Si](C)(C)C	2057.8	Standard polar	33892256
(R)-Menthone 8-thioacetate,1TBDMS,isomer #1	CC(=O)SC(C)(C)C1=C(O[Si](C)(C)C(C)(C)C)C[C@@H](C)CC1	1944.7	Semi standard non polar	33892256
(R)-Menthone 8-thioacetate,1TBDMS,isomer #1	CC(=O)SC(C)(C)C1=C(O[Si](C)(C)C(C)(C)C)C[C@@H](C)CC1	1980.9	Standard non polar	33892256
(R)-Menthone 8-thioacetate,1TBDMS,isomer #1	CC(=O)SC(C)(C)C1=C(O[Si](C)(C)C(C)(C)C)C[C@@H](C)CC1	2182.5	Standard polar	33892256
(R)-Menthone 8-thioacetate,1TBDMS,isomer #2	CC(=O)SC(C)(C)[C@@H]1CC[C@H](C)C=C1O[Si](C)(C)C(C)(C)C	1933.0	Semi standard non polar	33892256
(R)-Menthone 8-thioacetate,1TBDMS,isomer #2	CC(=O)SC(C)(C)[C@@H]1CC[C@H](C)C=C1O[Si](C)(C)C(C)(C)C	1967.8	Standard non polar	33892256
(R)-Menthone 8-thioacetate,1TBDMS,isomer #2	CC(=O)SC(C)(C)[C@@H]1CC[C@H](C)C=C1O[Si](C)(C)C(C)(C)C	2195.0	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 10V, Positive-QTOF	splash10-002r-1950000000-2018fff359ffe024b7b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 20V, Positive-QTOF	splash10-02vi-9630000000-328278073e9c27dba070	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 40V, Positive-QTOF	splash10-016r-7900000000-41baa7b50f92a3e06f1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 10V, Negative-QTOF	splash10-000i-1940000000-972d7a95f41a42ba1c1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 20V, Negative-QTOF	splash10-000i-2910000000-6cf1874478173222b4bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 40V, Negative-QTOF	splash10-0006-9500000000-a0d98c63a2479feebb70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 10V, Positive-QTOF	splash10-0iki-4930000000-a7d1089cbca7d1147be3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 20V, Positive-QTOF	splash10-0570-9610000000-813c41e92f5466548cba	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 40V, Positive-QTOF	splash10-0596-9200000000-70836195c816766cc73f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 20V, Negative-QTOF	splash10-009i-7960000000-323e6906b1d13ae12838	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Menthone 8-thioacetate 40V, Negative-QTOF	splash10-00di-9200000000-78d4d5650254b065c53f	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

FDB016427

KNApSAcK ID

Not Available

Chemspider ID

19973410

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 (R)-Menthone 8-thioacetate (HMDB0303595)

MOL for HMDB0303595 ((R)-Menthone 8-thioacetate)

3D MOL for HMDB0303595 ((R)-Menthone 8-thioacetate)

3D SDF for HMDB0303595 ((R)-Menthone 8-thioacetate)

3D-SDF for HMDB0303595 ((R)-Menthone 8-thioacetate)

PDB for HMDB0303595 ((R)-Menthone 8-thioacetate)

3D PDB for HMDB0303595 ((R)-Menthone 8-thioacetate)

SMILES for HMDB0303595 ((R)-Menthone 8-thioacetate)

INCHI for HMDB0303595 ((R)-Menthone 8-thioacetate)

Structure for HMDB0303595 ((R)-Menthone 8-thioacetate)

3D Structure for HMDB0303595 ((R)-Menthone 8-thioacetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra