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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:37:54 UTC

Update Date

2022-03-07 02:55:18 UTC

HMDB ID

HMDB0037386

Secondary Accession Numbers

HMDB37386

Metabolite Identification

Common Name

(S)-Menthone 8-thioacetate

Description

(S)-Menthone 8-thioacetate 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 (S)-Menthone 8-thioacetate.

Structure

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

HMDB0037386
     RDKit          3D
(S)-Menthone 8-thioacetate
 35 35  0  0  0  0  0  0  0  0999 V2000
   -4.4720    0.0194    1.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2727    0.3848    0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7217    1.4619    1.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079   -0.7367   -0.2993 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728   -0.0109   -1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6387    1.1639   -1.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6755   -1.0607   -2.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0731    0.3211   -0.1577 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3880   -0.9300    0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6019   -0.5565    1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7660   -0.4739    0.4177 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0008   -0.0255    1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4831    0.3999   -0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004    0.9358   -0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433    2.0057   -1.3944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8519   -0.9746    1.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2689    0.7624    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2785    0.1412    2.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9784    1.3040   -2.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6730    0.9170   -2.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7592    2.0958   -1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7828   -2.0434   -1.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3490   -1.0322   -3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3747   -0.8510   -2.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4783    1.0377    0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4063   -1.3699    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471   -1.6503   -0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676    0.3638    1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002   -1.4016    2.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -1.5173    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3676   -0.8688    1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120    0.2839    0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7570    0.7951    1.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1985    1.2522   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6834   -0.1422   -1.7166 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  6
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
M  END


  Mrv0541 10241203442D          

 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  1  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  1  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>
HMDB0037386

> <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-WPRPVWTQSA-N

> <FORMULA>
C12H20O2S

> <MOLECULAR_WEIGHT>
228.351

> <EXACT_MASS>
228.118400574

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.94250508484747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037386
     RDKit          3D
(S)-Menthone 8-thioacetate
 35 35  0  0  0  0  0  0  0  0999 V2000
   -4.4720    0.0194    1.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2727    0.3848    0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7217    1.4619    1.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079   -0.7367   -0.2993 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728   -0.0109   -1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6387    1.1639   -1.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6755   -1.0607   -2.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0731    0.3211   -0.1577 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3880   -0.9300    0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6019   -0.5565    1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7660   -0.4739    0.4177 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0008   -0.0255    1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4831    0.3999   -0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004    0.9358   -0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433    2.0057   -1.3944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8519   -0.9746    1.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2689    0.7624    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2785    0.1412    2.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9784    1.3040   -2.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6730    0.9170   -2.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7592    2.0958   -1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7828   -2.0434   -1.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3490   -1.0322   -3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3747   -0.8510   -2.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4783    1.0377    0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4063   -1.3699    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471   -1.6503   -0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676    0.3638    1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002   -1.4016    2.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -1.5173    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3676   -0.8688    1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120    0.2839    0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7570    0.7951    1.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1985    1.2522   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6834   -0.1422   -1.7166 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  6
 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    HMDB0037386
HETATM    1  C1  UNL     1      -4.472   0.019   1.746  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.273   0.385   0.920  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.722   1.462   1.064  1.00  0.00           O  
HETATM    4  S1  UNL     1      -2.608  -0.737  -0.299  1.00  0.00           S  
HETATM    5  C3  UNL     1      -1.173  -0.011  -1.131  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.639   1.164  -1.924  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.675  -1.061  -2.133  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.073   0.321  -0.158  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.388  -0.930   0.560  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.602  -0.556   1.375  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.766  -0.474   0.418  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.001  -0.026   1.171  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.483   0.400  -0.773  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.100   0.936  -0.787  1.00  0.00           C  
HETATM   15  O2  UNL     1       0.943   2.006  -1.394  1.00  0.00           O  
HETATM   16  H1  UNL     1      -4.852  -0.975   1.481  1.00  0.00           H  
HETATM   17  H2  UNL     1      -5.269   0.762   1.495  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.278   0.141   2.831  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.978   1.304  -2.810  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.673   0.917  -2.308  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.759   2.096  -1.339  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.783  -2.043  -1.655  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.349  -1.032  -3.011  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.375  -0.851  -2.427  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.478   1.038   0.581  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.406  -1.370   1.193  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.747  -1.650  -0.233  1.00  0.00           H  
HETATM   28  H13 UNL     1       1.468   0.364   1.964  1.00  0.00           H  
HETATM   29  H14 UNL     1       1.800  -1.402   2.078  1.00  0.00           H  
HETATM   30  H15 UNL     1       2.969  -1.517   0.066  1.00  0.00           H  
HETATM   31  H16 UNL     1       4.368  -0.869   1.793  1.00  0.00           H  
HETATM   32  H17 UNL     1       4.812   0.284   0.475  1.00  0.00           H  
HETATM   33  H18 UNL     1       3.757   0.795   1.863  1.00  0.00           H  
HETATM   34  H19 UNL     1       3.198   1.252  -0.736  1.00  0.00           H  
HETATM   35  H20 UNL     1       2.683  -0.142  -1.717  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

HMDB0037386
     RDKit          3D
(S)-Menthone 8-thioacetate
 35 35  0  0  0  0  0  0  0  0999 V2000
   -4.4720    0.0194    1.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2727    0.3848    0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7217    1.4619    1.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6079   -0.7367   -0.2993 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728   -0.0109   -1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6387    1.1639   -1.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6755   -1.0607   -2.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0731    0.3211   -0.1577 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3880   -0.9300    0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6019   -0.5565    1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7660   -0.4739    0.4177 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0008   -0.0255    1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4831    0.3999   -0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1004    0.9358   -0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433    2.0057   -1.3944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8519   -0.9746    1.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2689    0.7624    1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2785    0.1412    2.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9784    1.3040   -2.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6730    0.9170   -2.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7592    2.0958   -1.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7828   -2.0434   -1.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3490   -1.0322   -3.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3747   -0.8510   -2.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4783    1.0377    0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4063   -1.3699    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471   -1.6503   -0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676    0.3638    1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002   -1.4016    2.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -1.5173    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3676   -0.8688    1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120    0.2839    0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7570    0.7951    1.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1985    1.2522   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6834   -0.1422   -1.7166 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  6
 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
(S)-Menthone 8-thioacetic acid	Generator
8-acetylthio-P-Menthanone-3	HMDB
FEMA 3809	HMDB
Menthone 8-thioacetate	HMDB
(2S,5S)-2-[2-(Acetylsulphanyl)propan-2-yl]-5-methylcyclohexan-1-one	Generator

Chemical Formula

C₁₂H₂₀O₂S

Average Molecular Weight

228.351

Monoisotopic Molecular Weight

228.118400574

IUPAC Name

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

Traditional Name

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

CAS Registry Number

57129-12-1

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-WPRPVWTQSA-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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037386)

Source

Endogenous

Endogenous (HMDB: HMDB0037386)

Animal

Animal (HMDB: HMDB0037386)

Exogenous

Food

Food (HMDB: HMDB0037386)

Exogenous (HMDB: HMDB0037386)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037386)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037386)

Lipid metabolism pathway (HMDB: HMDB0037386)

Cellular process

Cell signaling (HMDB: HMDB0037386)

Biochemical process

Lipid transport (HMDB: HMDB0037386)

Role

Biological role

Energy source (HMDB: HMDB0037386)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037386)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037386)

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	392.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.092 g/L	ALOGPS
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	25.94 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]+	154.141	31661259
DarkChem	[M-H]-	148.789	31661259
DeepCCS	[M+H]+	155.554	30932474
DeepCCS	[M-H]-	153.159	30932474
DeepCCS	[M-2H]-	186.08	30932474
DeepCCS	[M+Na]+	161.467	30932474
AllCCS	[M+H]+	149.8	32859911
AllCCS	[M+H-H2O]+	146.2	32859911
AllCCS	[M+NH4]+	153.1	32859911
AllCCS	[M+Na]+	154.0	32859911
AllCCS	[M-H]-	157.6	32859911
AllCCS	[M+Na-2H]-	158.6	32859911
AllCCS	[M+HCOO]-	159.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.38 minutes	32390414
Predicted by Siyang on May 30, 2022	15.2545 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2279.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	477.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	236.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	134.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	536.6 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	542.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	66.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1142.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	431.9 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	1121.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	345.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	426.8 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	11.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Menthone 8-thioacetate	C[C@H]1CC[C@@H](C(=O)C1)C(C)(C)SC(C)=O	2178.2	Standard polar	33892256
(S)-Menthone 8-thioacetate	C[C@H]1CC[C@@H](C(=O)C1)C(C)(C)SC(C)=O	1624.6	Standard non polar	33892256
(S)-Menthone 8-thioacetate	C[C@H]1CC[C@@H](C(=O)C1)C(C)(C)SC(C)=O	1663.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-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
(S)-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
(S)-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
(S)-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
(S)-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
(S)-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
(S)-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
(S)-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

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Menthone 8-thioacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-05mo-9210000000-be3f8d1e48d597a124fd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Menthone 8-thioacetate 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 - (S)-Menthone 8-thioacetate 10V, Positive-QTOF	splash10-002r-1950000000-2018fff359ffe024b7b6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Menthone 8-thioacetate 20V, Positive-QTOF	splash10-02vi-9630000000-328278073e9c27dba070	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Menthone 8-thioacetate 40V, Positive-QTOF	splash10-016r-7900000000-41baa7b50f92a3e06f1c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-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 - (S)-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 - (S)-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 - (S)-Menthone 8-thioacetate 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Menthone 8-thioacetate 20V, Negative-QTOF	splash10-009i-7960000000-323e6906b1d13ae12838	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Menthone 8-thioacetate 40V, Negative-QTOF	splash10-00di-9200000000-78d4d5650254b065c53f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Menthone 8-thioacetate 10V, Positive-QTOF	splash10-0iki-4930000000-a7d1089cbca7d1147be3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Menthone 8-thioacetate 20V, Positive-QTOF	splash10-0570-9610000000-813c41e92f5466548cba	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Menthone 8-thioacetate 40V, Positive-QTOF	splash10-0596-9200000000-70836195c816766cc73f	2021-09-23	Wishart 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

FDB016428

KNApSAcK ID

Not Available

Chemspider ID

30777186

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92649

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1524301

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 (S)-Menthone 8-thioacetate (HMDB0037386)

MOL for HMDB0037386 ((S)-Menthone 8-thioacetate)

3D MOL for HMDB0037386 ((S)-Menthone 8-thioacetate)

3D SDF for HMDB0037386 ((S)-Menthone 8-thioacetate)

3D-SDF for HMDB0037386 ((S)-Menthone 8-thioacetate)

PDB for HMDB0037386 ((S)-Menthone 8-thioacetate)

3D PDB for HMDB0037386 ((S)-Menthone 8-thioacetate)

SMILES for HMDB0037386 ((S)-Menthone 8-thioacetate)

INCHI for HMDB0037386 ((S)-Menthone 8-thioacetate)

Structure for HMDB0037386 ((S)-Menthone 8-thioacetate)

3D Structure for HMDB0037386 ((S)-Menthone 8-thioacetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra