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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 07:16:11 UTC

Update Date

2021-09-24 07:16:11 UTC

HMDB ID

HMDB0304111

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-(6'-methylthio)hexylmalate

Description

3-(6'-methylthio)hexylmalate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 3-(6'-methylthio)hexylmalate can be found in a number of food items such as feijoa, chanterelle, pepper (c. baccatum), and date, which makes 3-(6'-methylthio)hexylmalate a potential biomarker for the consumption of these food products.

Structure

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

HMDB0304111
     RDKit          3D
3-(6'-methylthio)hexylmalate
 35 34  0  0  0  0  0  0  0  0999 V2000
    5.7303   -0.6001    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2182   -1.5352    0.6805 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8899   -0.8772   -0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247    0.5632   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375    1.1743   -0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175    0.4440   -0.7176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3091    0.4290    0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6047   -0.3070    0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7028    0.2904   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0406    1.6676    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2903    2.6590   -0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862    1.9946    0.8906 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.9211   -0.5912   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4555   -1.8203   -0.6741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4631   -0.8771    1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2070   -0.0954    1.8463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1423   -2.0790    1.8865 O   0  0  0  0  0  1  0  0  0  0  0  0
    6.6091   -0.9501    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5098    0.4685    0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436   -0.7367   -0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1665   -0.9876   -1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9675   -1.4789   -0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443    1.1641   -0.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3022    0.5759    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    1.0517   -1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441    2.2591   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535   -0.5752   -1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4762    0.9610   -1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476    1.4275    1.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210   -0.1586    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -1.3490    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233   -0.3317    1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    0.2619   -1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6679   -0.1706   -0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6542   -1.8711   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 13 34  1  0
 14 35  1  0
M  CHG  2  12  -1  17  -1
M  END

  Mrv1533005141521392D          

 17 16  0  0  0  0            999 V2000
    3.5211    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.2368    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    1.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    1.6204    0.0000 O   0  5  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  CHG  2  14  -1  17  -1
M  END
> <DATABASE_ID>
HMDB0304111

> <DATABASE_NAME>
hmdb

> <SMILES>
CSCCCCCCC(C(O)C([O-])=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H20O5S/c1-17-7-5-3-2-4-6-8(10(13)14)9(12)11(15)16/h8-9,12H,2-7H2,1H3,(H,13,14)(H,15,16)/p-2

> <INCHI_KEY>
LQQZHLHCFSCJCU-UHFFFAOYSA-L

> <FORMULA>
C11H18O5S

> <MOLECULAR_WEIGHT>
262.32

> <EXACT_MASS>
262.088592013

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.38326224961748

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-[6-(methylsulfanyl)hexyl]butanedioate

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.853888164666667

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.578658641587203

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.838796737605913

> <JCHEM_PKA_STRONGEST_BASIC>
-4.012149840589015

> <JCHEM_POLAR_SURFACE_AREA>
100.49000000000001

> <JCHEM_REFRACTIVITY>
86.7372

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-[6-(methylsulfanyl)hexyl]butanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304111
     RDKit          3D
3-(6'-methylthio)hexylmalate
 35 34  0  0  0  0  0  0  0  0999 V2000
    5.7303   -0.6001    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2182   -1.5352    0.6805 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8899   -0.8772   -0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247    0.5632   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375    1.1743   -0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175    0.4440   -0.7176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3091    0.4290    0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6047   -0.3070    0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7028    0.2904   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0406    1.6676    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2903    2.6590   -0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862    1.9946    0.8906 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.9211   -0.5912   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4555   -1.8203   -0.6741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4631   -0.8771    1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2070   -0.0954    1.8463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1423   -2.0790    1.8865 O   0  0  0  0  0  1  0  0  0  0  0  0
    6.6091   -0.9501    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5098    0.4685    0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436   -0.7367   -0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1665   -0.9876   -1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9675   -1.4789   -0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443    1.1641   -0.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3022    0.5759    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    1.0517   -1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441    2.2591   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535   -0.5752   -1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4762    0.9610   -1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476    1.4275    1.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210   -0.1586    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -1.3490    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233   -0.3317    1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    0.2619   -1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6679   -0.1706   -0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6542   -1.8711   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 13 34  1  0
 14 35  1  0
M  CHG  2  12  -1  17  -1
M  END

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  C   UNK     0       6.573   5.335   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       7.906   6.105   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      18.576   7.645   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O-1
HETATM   15  C   UNK     0      17.242   3.795   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      18.576   3.025   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      15.908   3.025   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0304111
HETATM    1  C1  UNL     1       5.730  -0.600   0.228  1.00  0.00           C  
HETATM    2  S1  UNL     1       4.218  -1.535   0.680  1.00  0.00           S  
HETATM    3  C2  UNL     1       2.890  -0.877  -0.385  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.625   0.563  -0.005  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.538   1.174  -0.848  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.217   0.444  -0.718  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.309   0.429   0.673  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.605  -0.307   0.742  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.703   0.290  -0.124  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.041   1.668   0.215  1.00  0.00           C  
HETATM   11  O1  UNL     1      -2.290   2.659  -0.096  1.00  0.00           O  
HETATM   12  O2  UNL     1      -4.186   1.995   0.891  1.00  0.00           O1-
HETATM   13  C10 UNL     1      -3.921  -0.591  -0.116  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.455  -1.820  -0.674  1.00  0.00           O  
HETATM   15  C11 UNL     1      -4.463  -0.877   1.234  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.207  -0.095   1.846  1.00  0.00           O  
HETATM   17  O5  UNL     1      -4.142  -2.079   1.886  1.00  0.00           O1-
HETATM   18  H1  UNL     1       6.609  -0.950   0.780  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.510   0.468   0.436  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.944  -0.737  -0.860  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.167  -0.988  -1.446  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.967  -1.479  -0.225  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.544   1.164  -0.123  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.302   0.576   1.046  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.853   1.052  -1.914  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.444   2.259  -0.682  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.354  -0.575  -1.076  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.476   0.961  -1.418  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.348   1.427   1.151  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.421  -0.159   1.297  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.484  -1.349   0.421  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.023  -0.332   1.778  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.357   0.262  -1.208  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.668  -0.171  -0.813  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.654  -1.871  -1.631  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8   29   30
CONECT    8    9   31   32
CONECT    9   10   13   33
CONECT   10   11   11   12
CONECT   13   14   15   34
CONECT   14   35
CONECT   15   16   16   17
END

HMDB0304111
     RDKit          3D
3-(6'-methylthio)hexylmalate
 35 34  0  0  0  0  0  0  0  0999 V2000
    5.7303   -0.6001    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2182   -1.5352    0.6805 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8899   -0.8772   -0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247    0.5632   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375    1.1743   -0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175    0.4440   -0.7176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3091    0.4290    0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6047   -0.3070    0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7028    0.2904   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0406    1.6676    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2903    2.6590   -0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862    1.9946    0.8906 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.9211   -0.5912   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4555   -1.8203   -0.6741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4631   -0.8771    1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2070   -0.0954    1.8463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1423   -2.0790    1.8865 O   0  0  0  0  0  1  0  0  0  0  0  0
    6.6091   -0.9501    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5098    0.4685    0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436   -0.7367   -0.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1665   -0.9876   -1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9675   -1.4789   -0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443    1.1641   -0.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3022    0.5759    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    1.0517   -1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441    2.2591   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535   -0.5752   -1.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4762    0.9610   -1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476    1.4275    1.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210   -0.1586    1.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -1.3490    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233   -0.3317    1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    0.2619   -1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6679   -0.1706   -0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6542   -1.8711   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
 13 34  1  0
 14 35  1  0
M  CHG  2  12  -1  17  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-3-[6-(methylsulfanyl)hexyl]butanedioic acid	Generator
2-Hydroxy-3-[6-(methylsulphanyl)hexyl]butanedioate	Generator
2-Hydroxy-3-[6-(methylsulphanyl)hexyl]butanedioic acid	Generator
3-(6'-methylthio)Hexylmalic acid	MetaCyc, Generator

Chemical Formula

C₁₁H₁₈O₅S

Average Molecular Weight

262.32

Monoisotopic Molecular Weight

262.088592013

IUPAC Name

2-hydroxy-3-[6-(methylsulfanyl)hexyl]butanedioate

Traditional Name

2-hydroxy-3-[6-(methylsulfanyl)hexyl]butanedioate

CAS Registry Number

Not Available

SMILES

CSCCCCCCC(C(O)C([O-])=O)C([O-])=O

InChI Identifier

InChI=1S/C11H20O5S/c1-17-7-5-3-2-4-6-8(10(13)14)9(12)11(15)16/h8-9,12H,2-7H2,1H3,(H,13,14)(H,15,16)/p-2

InChI Key

LQQZHLHCFSCJCU-UHFFFAOYSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Branched fatty acid
Thia fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Dicarboxylic acid or derivatives
Monosaccharide
Secondary alcohol
Carboxylic acid derivative
Dialkylthioether
Carboxylic acid
Sulfenyl compound
Thioether
Alcohol
Organic oxygen compound
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

a small molecule (CPDQT-39 )

Ontology

Not Available

Exogenous (HMDB: HMDB0304111)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

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	1.72	ALOGPS
logP	1.85	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.84	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.49 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	86.74 m³·mol⁻¹	ChemAxon
Polarizability	27.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	159.983	32859911
AllCCS	[M+H-H2O]+	156.764	32859911
AllCCS	[M+Na]+	163.823	32859911
AllCCS	[M+NH4]+	162.966	32859911
AllCCS	[M-H]-	158.585	32859911
AllCCS	[M+Na-2H]-	159.163	32859911
AllCCS	[M+HCOO]-	159.91	32859911
DeepCCS	[M+H]+	155.817	30932474
DeepCCS	[M-H]-	152.365	30932474
DeepCCS	[M-2H]-	188.077	30932474
DeepCCS	[M+Na]+	164.369	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

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

FDB030398

KNApSAcK ID

Not Available

Chemspider ID

24784950

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44237339

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 3-(6'-methylthio)hexylmalate (HMDB0304111)

MOL for HMDB0304111 (3-(6'-methylthio)hexylmalate)

3D MOL for HMDB0304111 (3-(6'-methylthio)hexylmalate)

3D SDF for HMDB0304111 (3-(6'-methylthio)hexylmalate)

3D-SDF for HMDB0304111 (3-(6'-methylthio)hexylmalate)

PDB for HMDB0304111 (3-(6'-methylthio)hexylmalate)

3D PDB for HMDB0304111 (3-(6'-methylthio)hexylmalate)

SMILES for HMDB0304111 (3-(6'-methylthio)hexylmalate)

INCHI for HMDB0304111 (3-(6'-methylthio)hexylmalate)

Structure for HMDB0304111 (3-(6'-methylthio)hexylmalate)

3D Structure for HMDB0304111 (3-(6'-methylthio)hexylmalate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices