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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:35 UTC

Update Date

2022-03-07 02:53:17 UTC

HMDB ID

HMDB0032223

Secondary Accession Numbers

HMDB32223

Metabolite Identification

Common Name

Diisopentyl thiomalate

Description

Diisopentyl thiomalate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a significant number of articles have been published on Diisopentyl thiomalate.

Structure

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

HMDB0032223
     RDKit          3D
Diisopentyl thiomalate
 45 44  0  0  0  0  0  0  0  0999 V2000
   -6.5412    0.7537    1.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4720    0.5170    0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1815    0.2908   -0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6543   -0.6677    1.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -0.9781    0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7110    0.1512   -0.0031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6155    0.1679   -0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -0.8630   -1.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7007    1.3177   -1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    1.1441   -0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738    0.8159    1.3874 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926    0.1112   -1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040   -0.5419   -2.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -0.1950   -0.5628 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5339   -1.1777   -1.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857   -1.3738   -0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7511   -0.1479   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0609   -0.5628    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1775    0.9766    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5169    0.2954    1.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7045    1.8223    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2674    0.2153    2.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8539    1.4366    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5158    0.3549   -1.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6894   -0.6923   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9312    1.1212   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2398   -0.4912    2.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3373   -1.5533    1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0330   -1.2006   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0273   -1.8928    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580    2.2210   -0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5844    1.6297   -2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1551    2.1432   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482   -0.1137    1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134   -2.1760   -1.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5808   -0.9666   -2.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4275   -2.1365   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8229   -1.7750    0.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0387    0.1774   -1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7773   -0.7831    1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7965    0.2728    0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4507   -1.4816   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7831    1.7827   -0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9583    1.4180    0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605    0.6340    0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
M  END


  Mrv0541 05061306252D          

 19 18  0  0  0  0            999 V2000
    6.6217    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4783    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -0.1105    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  5  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  2  0  0  0  0
 17  7  1  0  0  0  0
 17 13  1  0  0  0  0
 18  8  1  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032223

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CCOC(=O)CC(S)C(=O)OCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H26O4S/c1-10(2)5-7-17-13(15)9-12(19)14(16)18-8-6-11(3)4/h10-12,19H,5-9H2,1-4H3

> <INCHI_KEY>
HHNLQBYPOOATIP-UHFFFAOYSA-N

> <FORMULA>
C14H26O4S

> <MOLECULAR_WEIGHT>
290.419

> <EXACT_MASS>
290.15518001

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.84584054844805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-bis(3-methylbutyl) 2-sulfanylbutanedioate

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
3.443796373333333

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.109193466597334

> <JCHEM_PKA_STRONGEST_BASIC>
-6.817192123630319

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
77.38480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-bis(3-methylbutyl) 2-sulfanylbutanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032223
     RDKit          3D
Diisopentyl thiomalate
 45 44  0  0  0  0  0  0  0  0999 V2000
   -6.5412    0.7537    1.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4720    0.5170    0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1815    0.2908   -0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6543   -0.6677    1.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -0.9781    0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7110    0.1512   -0.0031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6155    0.1679   -0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -0.8630   -1.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7007    1.3177   -1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    1.1441   -0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738    0.8159    1.3874 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926    0.1112   -1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040   -0.5419   -2.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -0.1950   -0.5628 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5339   -1.1777   -1.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857   -1.3738   -0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7511   -0.1479   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0609   -0.5628    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1775    0.9766    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5169    0.2954    1.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7045    1.8223    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2674    0.2153    2.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8539    1.4366    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5158    0.3549   -1.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6894   -0.6923   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9312    1.1212   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2398   -0.4912    2.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3373   -1.5533    1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0330   -1.2006   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0273   -1.8928    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580    2.2210   -0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5844    1.6297   -2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1551    2.1432   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482   -0.1137    1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134   -2.1760   -1.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5808   -0.9666   -2.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4275   -2.1365   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8229   -1.7750    0.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0387    0.1774   -1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7773   -0.7831    1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7965    0.2728    0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4507   -1.4816   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7831    1.7827   -0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9583    1.4180    0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605    0.6340    0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.361   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.027  -0.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.977   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.644   3.644   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.693   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.310   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.359   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.976   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.358   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.027   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.644   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.025   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.692   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.691   2.104   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.692  -0.206   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.691   3.644   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.026   2.104   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.357   1.334   0.000  0.00  0.00           O+0
HETATM   19  S   UNK     0       3.025  -0.206   0.000  0.00  0.00           S+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   11                                                            
CONECT    5    7   10                                                       
CONECT    6    8   11                                                       
CONECT    7    5   17                                                       
CONECT    8    6   18                                                       
CONECT    9   12   13                                                       
CONECT   10    1    2    5                                                  
CONECT   11    3    4    6                                                  
CONECT   12    9   14   19                                                  
CONECT   13    9   15   17                                                  
CONECT   14   12   16   18                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
CONECT   17    7   13                                                       
CONECT   18    8   14                                                       
CONECT   19   12                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0032223
HETATM    1  C1  UNL     1      -6.541   0.754   1.745  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.472   0.517   0.681  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.181   0.291  -0.630  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.654  -0.668   1.102  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.566  -0.978   0.104  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.711   0.151  -0.003  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.615   0.168  -0.856  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.409  -0.863  -1.534  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.701   1.318  -1.001  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.648   1.144  -0.407  1.00  0.00           C  
HETATM   11  S1  UNL     1       0.574   0.816   1.387  1.00  0.00           S  
HETATM   12  C9  UNL     1       1.493   0.111  -1.038  1.00  0.00           C  
HETATM   13  O3  UNL     1       1.104  -0.542  -2.034  1.00  0.00           O  
HETATM   14  O4  UNL     1       2.769  -0.195  -0.563  1.00  0.00           O  
HETATM   15  C10 UNL     1       3.534  -1.178  -1.188  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.886  -1.374  -0.555  1.00  0.00           C  
HETATM   17  C12 UNL     1       5.751  -0.148  -0.565  1.00  0.00           C  
HETATM   18  C13 UNL     1       7.061  -0.563   0.119  1.00  0.00           C  
HETATM   19  C14 UNL     1       5.178   0.977   0.268  1.00  0.00           C  
HETATM   20  H1  UNL     1      -7.517   0.295   1.417  1.00  0.00           H  
HETATM   21  H2  UNL     1      -6.705   1.822   1.937  1.00  0.00           H  
HETATM   22  H3  UNL     1      -6.267   0.215   2.690  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.854   1.437   0.635  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.516   0.355  -1.513  1.00  0.00           H  
HETATM   25  H6  UNL     1      -6.689  -0.692  -0.633  1.00  0.00           H  
HETATM   26  H7  UNL     1      -6.931   1.121  -0.759  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.240  -0.491   2.112  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.337  -1.553   1.183  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.033  -1.201  -0.882  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.027  -1.893   0.415  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.158   2.221  -0.496  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.584   1.630  -2.066  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.155   2.143  -0.483  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.548  -0.114   1.732  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.013  -2.176  -1.084  1.00  0.00           H  
HETATM   36  H17 UNL     1       3.581  -0.967  -2.270  1.00  0.00           H  
HETATM   37  H18 UNL     1       5.428  -2.137  -1.181  1.00  0.00           H  
HETATM   38  H19 UNL     1       4.823  -1.775   0.455  1.00  0.00           H  
HETATM   39  H20 UNL     1       6.039   0.177  -1.586  1.00  0.00           H  
HETATM   40  H21 UNL     1       6.777  -0.783   1.182  1.00  0.00           H  
HETATM   41  H22 UNL     1       7.797   0.273   0.113  1.00  0.00           H  
HETATM   42  H23 UNL     1       7.451  -1.482  -0.335  1.00  0.00           H  
HETATM   43  H24 UNL     1       4.783   1.783  -0.383  1.00  0.00           H  
HETATM   44  H25 UNL     1       5.958   1.418   0.917  1.00  0.00           H  
HETATM   45  H26 UNL     1       4.360   0.634   0.936  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4   23
CONECT    3   24   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   31   32
CONECT   10   11   12   33
CONECT   11   34
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   35   36
CONECT   16   17   37   38
CONECT   17   18   19   39
CONECT   18   40   41   42
CONECT   19   43   44   45
END

HMDB0032223
     RDKit          3D
Diisopentyl thiomalate
 45 44  0  0  0  0  0  0  0  0999 V2000
   -6.5412    0.7537    1.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4720    0.5170    0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1815    0.2908   -0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6543   -0.6677    1.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -0.9781    0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7110    0.1512   -0.0031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6155    0.1679   -0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -0.8630   -1.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7007    1.3177   -1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    1.1441   -0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738    0.8159    1.3874 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926    0.1112   -1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040   -0.5419   -2.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -0.1950   -0.5628 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5339   -1.1777   -1.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857   -1.3738   -0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7511   -0.1479   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0609   -0.5628    0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1775    0.9766    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5169    0.2954    1.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7045    1.8223    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2674    0.2153    2.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8539    1.4366    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5158    0.3549   -1.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6894   -0.6923   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9312    1.1212   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2398   -0.4912    2.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3373   -1.5533    1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0330   -1.2006   -0.8825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0273   -1.8928    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580    2.2210   -0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5844    1.6297   -2.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1551    2.1432   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482   -0.1137    1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134   -2.1760   -1.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5808   -0.9666   -2.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4275   -2.1365   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8229   -1.7750    0.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0387    0.1774   -1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7773   -0.7831    1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7965    0.2728    0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4507   -1.4816   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7831    1.7827   -0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9583    1.4180    0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605    0.6340    0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Diisopentyl thiomalic acid	Generator

Chemical Formula

C₁₄H₂₆O₄S

Average Molecular Weight

290.419

Monoisotopic Molecular Weight

290.15518001

IUPAC Name

1,4-bis(3-methylbutyl) 2-sulfanylbutanedioate

Traditional Name

1,4-bis(3-methylbutyl) 2-sulfanylbutanedioate

CAS Registry Number

68084-03-7

SMILES

CC(C)CCOC(=O)CC(S)C(=O)OCCC(C)C

InChI Identifier

InChI=1S/C14H26O4S/c1-10(2)5-7-17-13(15)9-12(19)14(16)18-8-6-11(3)4/h10-12,19H,5-9H2,1-4H3

InChI Key

HHNLQBYPOOATIP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Alkylthiol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0032223)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032223)

Source

Endogenous

Endogenous (HMDB: HMDB0032223)

Animal

Animal (HMDB: HMDB0032223)

Exogenous

Food

Food (HMDB: HMDB0032223)

Exogenous (HMDB: HMDB0032223)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032223)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032223)

Lipid metabolism pathway (HMDB: HMDB0032223)

Biochemical process

Lipid transport (HMDB: HMDB0032223)

Role

Biological role

Energy source (HMDB: HMDB0032223)

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
Water Solubility	0.018 g/L	ALOGPS
logP	4.26	ALOGPS
logP	3.44	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	77.38 m³·mol⁻¹	ChemAxon
Polarizability	32.85 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
DarkChem	[M+H]+	171.092	31661259
DarkChem	[M-H]-	165.173	31661259
DeepCCS	[M+H]+	172.316	30932474
DeepCCS	[M-H]-	169.958	30932474
DeepCCS	[M-2H]-	202.843	30932474
DeepCCS	[M+Na]+	178.409	30932474
AllCCS	[M+H]+	170.8	32859911
AllCCS	[M+H-H2O]+	168.2	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.0	32859911
AllCCS	[M-H]-	169.7	32859911
AllCCS	[M+Na-2H]-	171.0	32859911
AllCCS	[M+HCOO]-	172.5	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.	8.33 minutes	32390414
Predicted by Siyang on May 30, 2022	20.7783 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.83 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3390.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	670.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	240.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	387.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	244.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	950.7 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	1115.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	156.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1612.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	652.0 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	2016.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	564.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	473.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	608.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	509.1 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	20.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diisopentyl thiomalate	CC(C)CCOC(=O)CC(S)C(=O)OCCC(C)C	2520.3	Standard polar	33892256
Diisopentyl thiomalate	CC(C)CCOC(=O)CC(S)C(=O)OCCC(C)C	1726.5	Standard non polar	33892256
Diisopentyl thiomalate	CC(C)CCOC(=O)CC(S)C(=O)OCCC(C)C	1871.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diisopentyl thiomalate,1TMS,isomer #1	CC(C)CCOC(=O)CC(S[Si](C)(C)C)C(=O)OCCC(C)C	2013.7	Semi standard non polar	33892256
Diisopentyl thiomalate,1TMS,isomer #1	CC(C)CCOC(=O)CC(S[Si](C)(C)C)C(=O)OCCC(C)C	1938.4	Standard non polar	33892256
Diisopentyl thiomalate,1TBDMS,isomer #1	CC(C)CCOC(=O)CC(S[Si](C)(C)C(C)(C)C)C(=O)OCCC(C)C	2224.6	Semi standard non polar	33892256
Diisopentyl thiomalate,1TBDMS,isomer #1	CC(C)CCOC(=O)CC(S[Si](C)(C)C(C)(C)C)C(=O)OCCC(C)C	2114.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Diisopentyl thiomalate GC-MS (Non-derivatized) - 70eV, Positive	splash10-002o-9450000000-711b537fc3e05c9c168d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diisopentyl thiomalate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diisopentyl thiomalate 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 - Diisopentyl thiomalate 10V, Positive-QTOF	splash10-0fdo-2390000000-00bd1220acb943d52c87	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopentyl thiomalate 20V, Positive-QTOF	splash10-00di-9400000000-9c72d5ab545d45fab5ea	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopentyl thiomalate 40V, Positive-QTOF	splash10-05fr-9200000000-f61a34913582ae064282	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopentyl thiomalate 10V, Negative-QTOF	splash10-0f79-2190000000-b4b94bf17446648e4c63	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopentyl thiomalate 20V, Negative-QTOF	splash10-0f9i-5930000000-52d89a33b9cf452cbbf0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopentyl thiomalate 40V, Negative-QTOF	splash10-0a4r-8910000000-efb3e391d2cda52073cf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopentyl thiomalate 10V, Negative-QTOF	splash10-000i-2490000000-330f59cfb39e9f3039d5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopentyl thiomalate 20V, Negative-QTOF	splash10-0gwn-4930000000-97baa4a96be85fba2ab2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopentyl thiomalate 40V, Negative-QTOF	splash10-0pb9-6910000000-2d43085581edfb81a21e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopentyl thiomalate 10V, Positive-QTOF	splash10-0006-1290000000-c5e4af69cc4440c40724	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopentyl thiomalate 20V, Positive-QTOF	splash10-0fki-8930000000-d6f60bf8184dc8b07c56	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diisopentyl thiomalate 40V, Positive-QTOF	splash10-00di-9000000000-78aba4c2915ee7da16b5	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB009296

KNApSAcK ID

Not Available

Chemspider ID

95905

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

106530

PDB ID

Not Available

ChEBI ID

38708

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

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 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Diisopentyl thiomalate (HMDB0032223)

MOL for HMDB0032223 (Diisopentyl thiomalate)

3D MOL for HMDB0032223 (Diisopentyl thiomalate)

3D SDF for HMDB0032223 (Diisopentyl thiomalate)

3D-SDF for HMDB0032223 (Diisopentyl thiomalate)

PDB for HMDB0032223 (Diisopentyl thiomalate)

3D PDB for HMDB0032223 (Diisopentyl thiomalate)

SMILES for HMDB0032223 (Diisopentyl thiomalate)

INCHI for HMDB0032223 (Diisopentyl thiomalate)

Structure for HMDB0032223 (Diisopentyl thiomalate)

3D Structure for HMDB0032223 (Diisopentyl thiomalate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra