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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:45:46 UTC

HMDB ID

HMDB0001526

Secondary Accession Numbers

HMDB0006951
HMDB01526
HMDB06951

Metabolite Identification

Common Name

S-Acetyldihydrolipoamide

Description

S-Acetyldihydrolipoamide is a thio-acetylated form of dihydrolipoamide. The molecule is commonly conjugated to lysine residues. The structure shown is the free form of the molecule. Pyruvate dehydrogenase complex. The reaction is 2-(alpha-hydroxyethyl)-TPP + lipoamide => S-acetyldihydrolipoamide + TPP [Homo sapiens], occuring in mitochondrial matrix. (reactome.org). S-Acetyldihydrolipoamide is an intermediate in alanine, aspartate and pyruvate metabolism and glycolysis/gluconeogenesis (KEGG:C01136). It is converted from 2-hydroxyethyl-THPP and lipoamide via the enzyme pyruvate dehydrogenase (EC:1.2.4.1). It is then converted to acetyl-CoA via the enzyme pyruvate dehydrogenase E2 component (dihydrolipoamide acetyltransferase) (EC:2.3.1.12).

Structure

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

HMDB0001526
     RDKit          3D
S-Acetyldihydrolipoamide
 34 33  0  0  0  0  0  0  0  0999 V2000
   -3.7581   -2.6574    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597   -1.4924   -0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5060   -1.1274   -1.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2924   -0.6187    1.3258 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2060    0.7674    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113    1.7923    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    3.0007   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3253    4.1476   -1.0999 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0219    0.2543    0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6968   -0.7446    1.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081   -1.3332    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418   -0.2882   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1235   -0.9026   -0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -0.1324   -1.1109 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1813   -2.1433   -0.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3848   -3.5654   -0.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7823   -2.4615   -0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9403   -2.8745    1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8222    1.1636    1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840    1.3636   -0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226    2.1255    0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7102    3.4923    0.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322    2.7106   -0.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6397    3.6587   -1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6665    1.0881   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3894   -0.2707   -0.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0193   -1.6038    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9147   -0.3538    2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5455   -1.8761   -0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3816   -2.0537    1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524    0.3913   -0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2664    0.2756    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2275    0.4991   -1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1130   -0.2312   -0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
M  END


  Mrv0541 02231219112D          

 15 14  0  0  0  0            999 V2000
   -1.1896   -0.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4793   -0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1896    0.6378    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9033   -0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2379   -0.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4793    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205   -0.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9551   -0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2379    0.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4793    1.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205    0.6378    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -0.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3826   -0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0928   -0.1931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3826   -1.4309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001526

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)SC(CCS)CCCCC(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13)

> <INCHI_KEY>
ARGXEXVCHMNAQU-UHFFFAOYSA-N

> <FORMULA>
C10H19NO2S2

> <MOLECULAR_WEIGHT>
249.393

> <EXACT_MASS>
249.085720237

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.661351810788403

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(acetylsulfanyl)-8-sulfanyloctanamide

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
1.2364680790000007

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.552166740788277

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.190901379680659

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5791099252102924

> <JCHEM_POLAR_SURFACE_AREA>
60.160000000000004

> <JCHEM_REFRACTIVITY>
67.22659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S(6)-acetyldihydrolipoamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001526
     RDKit          3D
S-Acetyldihydrolipoamide
 34 33  0  0  0  0  0  0  0  0999 V2000
   -3.7581   -2.6574    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597   -1.4924   -0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5060   -1.1274   -1.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2924   -0.6187    1.3258 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2060    0.7674    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113    1.7923    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    3.0007   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3253    4.1476   -1.0999 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0219    0.2543    0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6968   -0.7446    1.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081   -1.3332    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418   -0.2882   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1235   -0.9026   -0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -0.1324   -1.1109 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1813   -2.1433   -0.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3848   -3.5654   -0.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7823   -2.4615   -0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9403   -2.8745    1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8222    1.1636    1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840    1.3636   -0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226    2.1255    0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7102    3.4923    0.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322    2.7106   -0.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6397    3.6587   -1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6665    1.0881   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3894   -0.2707   -0.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0193   -1.6038    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9147   -0.3538    2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5455   -1.8761   -0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3816   -2.0537    1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524    0.3913   -0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2664    0.2756    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2275    0.4991   -1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1130   -0.2312   -0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.221  -0.360   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.895  -1.133   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      -2.221   1.191   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      -3.553  -1.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.444  -0.360   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.895   1.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.892  -0.360   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.783  -1.133   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.444   1.191   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.895   3.495   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0      -4.892   1.191   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0       3.115  -0.360   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.448  -1.133   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.773  -0.360   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       4.448  -2.671   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    9   10                                                  
CONECT    7    4   11                                                       
CONECT    8    5   12                                                       
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0001526
HETATM    1  C1  UNL     1      -3.758  -2.657   0.032  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.860  -1.492  -0.113  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.506  -1.127  -1.209  1.00  0.00           O  
HETATM    4  S1  UNL     1      -2.292  -0.619   1.326  1.00  0.00           S  
HETATM    5  C3  UNL     1      -1.206   0.767   0.923  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.011   1.792   0.182  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.241   3.001  -0.217  1.00  0.00           C  
HETATM    8  S2  UNL     1      -2.325   4.148  -1.100  1.00  0.00           S  
HETATM    9  C6  UNL     1      -0.022   0.254   0.152  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.697  -0.745   1.016  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.908  -1.333   0.349  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.942  -0.288  -0.019  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.124  -0.903  -0.671  1.00  0.00           C  
HETATM   14  N1  UNL     1       5.230  -0.132  -1.111  1.00  0.00           N  
HETATM   15  O2  UNL     1       4.181  -2.143  -0.855  1.00  0.00           O  
HETATM   16  H1  UNL     1      -3.385  -3.565  -0.491  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.782  -2.461  -0.394  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.940  -2.875   1.109  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.822   1.164   1.892  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.484   1.364  -0.699  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.823   2.125   0.890  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.710   3.492   0.625  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.432   2.711  -0.936  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.640   3.659  -1.015  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.666   1.088  -0.112  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.389  -0.271  -0.748  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.019  -1.604   1.159  1.00  0.00           H  
HETATM   28  H13 UNL     1       0.915  -0.354   2.028  1.00  0.00           H  
HETATM   29  H14 UNL     1       1.545  -1.876  -0.554  1.00  0.00           H  
HETATM   30  H15 UNL     1       2.382  -2.054   1.045  1.00  0.00           H  
HETATM   31  H16 UNL     1       2.452   0.391  -0.773  1.00  0.00           H  
HETATM   32  H17 UNL     1       3.266   0.276   0.856  1.00  0.00           H  
HETATM   33  H18 UNL     1       5.227   0.499  -1.931  1.00  0.00           H  
HETATM   34  H19 UNL     1       6.113  -0.231  -0.536  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    9   19
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8   24
CONECT    9   10   25   26
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   15   15
CONECT   14   33   34
END

HMDB0001526
     RDKit          3D
S-Acetyldihydrolipoamide
 34 33  0  0  0  0  0  0  0  0999 V2000
   -3.7581   -2.6574    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597   -1.4924   -0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5060   -1.1274   -1.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2924   -0.6187    1.3258 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2060    0.7674    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113    1.7923    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410    3.0007   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3253    4.1476   -1.0999 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0219    0.2543    0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6968   -0.7446    1.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081   -1.3332    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418   -0.2882   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1235   -0.9026   -0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -0.1324   -1.1109 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1813   -2.1433   -0.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3848   -3.5654   -0.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7823   -2.4615   -0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9403   -2.8745    1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8222    1.1636    1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4840    1.3636   -0.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226    2.1255    0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7102    3.4923    0.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322    2.7106   -0.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6397    3.6587   -1.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6665    1.0881   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3894   -0.2707   -0.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0193   -1.6038    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9147   -0.3538    2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5455   -1.8761   -0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3816   -2.0537    1.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524    0.3913   -0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2664    0.2756    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2275    0.4991   -1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1130   -0.2312   -0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-S-Acetyldihydrolipoamide	ChEBI
6-Acetylsulfanyl-8-sulfanyl-octanamide	HMDB
S-[6-Amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioate	HMDB
S-[6-Amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioic acid	HMDB

Chemical Formula

C₁₀H₁₉NO₂S₂

Average Molecular Weight

249.393

Monoisotopic Molecular Weight

249.085720237

IUPAC Name

6-(acetylsulfanyl)-8-sulfanyloctanamide

Traditional Name

S(6)-acetyldihydrolipoamide

CAS Registry Number

Not Available

SMILES

CC(=O)SC(CCS)CCCCC(N)=O

InChI Identifier

InChI=1S/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13)

InChI Key

ARGXEXVCHMNAQU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

Fatty amides

Alternative Parents

Substituents

Fatty amide
Carboxamide group
Primary carboxylic acid amide
Thiocarboxylic acid ester
Carbothioic s-ester
Sulfenyl compound
Thiocarboxylic acid or derivatives
Alkylthiol
Carboxylic acid derivative
Carbonyl group
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

S-substituted dihydrolipoamide (CHEBI:16807 )
a small molecule (S-ACETYLDIHYDROLIPOAMIDE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001526)
Cell membrane (HMDB: HMDB0001526)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001526)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001526)

Source

Endogenous

Endogenous (HMDB: HMDB0001526)

Plant

Animal

Animal (HMDB: HMDB0001526)

Exogenous

Food

Food (HMDB: HMDB0001526)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

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)

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)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

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

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001526)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0001526)
Glycolysis and Pyruvate Dehydrogenase (PathBank: SMP0000807)

Lipid metabolism pathway (HMDB: HMDB0001526)

Biochemical process

Lipid transport (HMDB: HMDB0001526)

Role

Biological role

Energy source (HMDB: HMDB0001526)

Physical Properties

State

Solid

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	0.036 g/L	ALOGPS
logP	2.46	ALOGPS
logP	1.24	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	10.19	ChemAxon
pKa (Strongest Basic)	-0.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.16 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	67.23 m³·mol⁻¹	ChemAxon
Polarizability	27.66 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]+	156.448	31661259
DarkChem	[M-H]-	154.149	31661259
AllCCS	[M+H]+	155.748	32859911
AllCCS	[M-H]-	159.988	32859911
DeepCCS	[M+H]+	158.578	30932474
DeepCCS	[M-H]-	155.667	30932474
DeepCCS	[M-2H]-	192.028	30932474
DeepCCS	[M+Na]+	167.69	30932474
AllCCS	[M+H]+	155.7	32859911
AllCCS	[M+H-H2O]+	152.6	32859911
AllCCS	[M+NH4]+	158.7	32859911
AllCCS	[M+Na]+	159.5	32859911
AllCCS	[M-H]-	160.0	32859911
AllCCS	[M+Na-2H]-	161.3	32859911
AllCCS	[M+HCOO]-	162.9	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.	4.58 minutes	32390414
Predicted by Siyang on May 30, 2022	12.8986 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.53 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2265.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	330.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	151.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	193.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	126.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	465.5 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	557.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	121.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1086.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	369.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1203.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	341.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	309.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	374.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	369.3 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	87.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-Acetyldihydrolipoamide	CC(=O)SC(CCS)CCCCC(N)=O	3328.3	Standard polar	33892256
S-Acetyldihydrolipoamide	CC(=O)SC(CCS)CCCCC(N)=O	1941.7	Standard non polar	33892256
S-Acetyldihydrolipoamide	CC(=O)SC(CCS)CCCCC(N)=O	2228.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-Acetyldihydrolipoamide,1TMS,isomer #1	CC(=O)SC(CCCCC(N)=O)CCS[Si](C)(C)C	2254.9	Semi standard non polar	33892256
S-Acetyldihydrolipoamide,1TMS,isomer #1	CC(=O)SC(CCCCC(N)=O)CCS[Si](C)(C)C	2164.7	Standard non polar	33892256
S-Acetyldihydrolipoamide,1TMS,isomer #1	CC(=O)SC(CCCCC(N)=O)CCS[Si](C)(C)C	3531.7	Standard polar	33892256
S-Acetyldihydrolipoamide,1TMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N[Si](C)(C)C	2185.9	Semi standard non polar	33892256
S-Acetyldihydrolipoamide,1TMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N[Si](C)(C)C	2111.8	Standard non polar	33892256
S-Acetyldihydrolipoamide,1TMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N[Si](C)(C)C	2864.9	Standard polar	33892256
S-Acetyldihydrolipoamide,2TMS,isomer #1	CC(=O)SC(CCCCC(=O)N[Si](C)(C)C)CCS[Si](C)(C)C	2334.2	Semi standard non polar	33892256
S-Acetyldihydrolipoamide,2TMS,isomer #1	CC(=O)SC(CCCCC(=O)N[Si](C)(C)C)CCS[Si](C)(C)C	2347.7	Standard non polar	33892256
S-Acetyldihydrolipoamide,2TMS,isomer #1	CC(=O)SC(CCCCC(=O)N[Si](C)(C)C)CCS[Si](C)(C)C	2849.4	Standard polar	33892256
S-Acetyldihydrolipoamide,2TMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2244.4	Semi standard non polar	33892256
S-Acetyldihydrolipoamide,2TMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2232.6	Standard non polar	33892256
S-Acetyldihydrolipoamide,2TMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2776.2	Standard polar	33892256
S-Acetyldihydrolipoamide,3TMS,isomer #1	CC(=O)SC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)CCS[Si](C)(C)C	2418.0	Semi standard non polar	33892256
S-Acetyldihydrolipoamide,3TMS,isomer #1	CC(=O)SC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)CCS[Si](C)(C)C	2446.9	Standard non polar	33892256
S-Acetyldihydrolipoamide,3TMS,isomer #1	CC(=O)SC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)CCS[Si](C)(C)C	2622.2	Standard polar	33892256
S-Acetyldihydrolipoamide,1TBDMS,isomer #1	CC(=O)SC(CCCCC(N)=O)CCS[Si](C)(C)C(C)(C)C	2499.9	Semi standard non polar	33892256
S-Acetyldihydrolipoamide,1TBDMS,isomer #1	CC(=O)SC(CCCCC(N)=O)CCS[Si](C)(C)C(C)(C)C	2400.1	Standard non polar	33892256
S-Acetyldihydrolipoamide,1TBDMS,isomer #1	CC(=O)SC(CCCCC(N)=O)CCS[Si](C)(C)C(C)(C)C	3524.1	Standard polar	33892256
S-Acetyldihydrolipoamide,1TBDMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N[Si](C)(C)C(C)(C)C	2411.5	Semi standard non polar	33892256
S-Acetyldihydrolipoamide,1TBDMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N[Si](C)(C)C(C)(C)C	2329.3	Standard non polar	33892256
S-Acetyldihydrolipoamide,1TBDMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N[Si](C)(C)C(C)(C)C	2924.4	Standard polar	33892256
S-Acetyldihydrolipoamide,2TBDMS,isomer #1	CC(=O)SC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)CCS[Si](C)(C)C(C)(C)C	2838.1	Semi standard non polar	33892256
S-Acetyldihydrolipoamide,2TBDMS,isomer #1	CC(=O)SC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)CCS[Si](C)(C)C(C)(C)C	2744.9	Standard non polar	33892256
S-Acetyldihydrolipoamide,2TBDMS,isomer #1	CC(=O)SC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)CCS[Si](C)(C)C(C)(C)C	2906.4	Standard polar	33892256
S-Acetyldihydrolipoamide,2TBDMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2712.2	Semi standard non polar	33892256
S-Acetyldihydrolipoamide,2TBDMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2638.2	Standard non polar	33892256
S-Acetyldihydrolipoamide,2TBDMS,isomer #2	CC(=O)SC(CCS)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2888.5	Standard polar	33892256
S-Acetyldihydrolipoamide,3TBDMS,isomer #1	CC(=O)SC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCS[Si](C)(C)C(C)(C)C	3150.7	Semi standard non polar	33892256
S-Acetyldihydrolipoamide,3TBDMS,isomer #1	CC(=O)SC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCS[Si](C)(C)C(C)(C)C	3015.8	Standard non polar	33892256
S-Acetyldihydrolipoamide,3TBDMS,isomer #1	CC(=O)SC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCS[Si](C)(C)C(C)(C)C	2858.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-Acetyldihydrolipoamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9310000000-0f17192770cd2eed81e2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-Acetyldihydrolipoamide 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-Acetyldihydrolipoamide 10V, Positive-QTOF	splash10-0pc0-0390000000-f4f7a106ce708d65c83c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide 20V, Positive-QTOF	splash10-001i-5590000000-4df718aaa87a6fbbd795	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide 40V, Positive-QTOF	splash10-03k9-4900000000-d4adb6f2a43bf9e5b1b9	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide 10V, Negative-QTOF	splash10-0a4j-2290000000-229a9fb285c737cc2c9f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide 20V, Negative-QTOF	splash10-0a4l-6590000000-6678ae77fcef8223dec9	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide 40V, Negative-QTOF	splash10-0006-9000000000-5de0a80883e527f54fbb	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide 10V, Positive-QTOF	splash10-0uxr-0490000000-9d67c94cbf8b72b1f312	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide 20V, Positive-QTOF	splash10-01x0-1940000000-dafc5697832c093d7224	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide 40V, Positive-QTOF	splash10-06tf-9600000000-853bdf0beb7957a18af3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide 10V, Negative-QTOF	splash10-03di-1390000000-2259a6df55463871f988	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide 20V, Negative-QTOF	splash10-00di-5950000000-5706c02348bf4fe9bb55	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-Acetyldihydrolipoamide 40V, Negative-QTOF	splash10-00dl-9200000000-a65938d00822602054fb	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022671

KNApSAcK ID

Not Available

Chemspider ID

1046

KEGG Compound ID

C01136

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6299

PubChem Compound

1076

PDB ID

Not Available

ChEBI ID

16807

Food Biomarker Ontology

Not Available

VMH ID

ADHLAM

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Yang YS, Frey PA: Dihydrolipoyl transacetylase of Escherichia coli. Formation of 8-S-acetyldihydrolipoamide. Biochemistry. 1986 Dec 16;25(25):8173-8. [PubMed:3101735 ]
Butterworth PJ, Tsai CS, Eley MH, Roche TE, Reed LJ: A kinetic study of dihydrolipoyl transacetylase from bovine kidney. J Biol Chem. 1975 Mar 10;250(5):1921-5. [PubMed:1089667 ]
O'Connor TP, Roche TE, Paukstelis JV: 13C nuclear magnetic resonance study of the pyruvate dehydrogenase-catalyzed acetylation of dihydrolipoamide. J Biol Chem. 1982 Mar 25;257(6):3110-2. [PubMed:6801041 ]

Enzymes

Enzyme Details

1. Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: PDHA1
Uniprot ID:: P08559
Molecular weight:: 43295.255

Enzyme Details

2. Dihydrolipoamide S-acetyltransferase

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: DLAT
Uniprot ID:: Q86YI5
Molecular weight:: 68996.0

Showing metabocard for S-Acetyldihydrolipoamide (HMDB0001526)

MOL for HMDB0001526 (S-Acetyldihydrolipoamide)

3D MOL for HMDB0001526 (S-Acetyldihydrolipoamide)

3D SDF for HMDB0001526 (S-Acetyldihydrolipoamide)

3D-SDF for HMDB0001526 (S-Acetyldihydrolipoamide)

PDB for HMDB0001526 (S-Acetyldihydrolipoamide)

3D PDB for HMDB0001526 (S-Acetyldihydrolipoamide)

SMILES for HMDB0001526 (S-Acetyldihydrolipoamide)

INCHI for HMDB0001526 (S-Acetyldihydrolipoamide)

Structure for HMDB0001526 (S-Acetyldihydrolipoamide)

3D Structure for HMDB0001526 (S-Acetyldihydrolipoamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes