MiMeDB: Showing metabocard for S-Acetyldihydrolipoamide (MMDBc0029666)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:36:43 UTC

Update Date

2024-04-30 19:40:22 UTC

Metabolite ID

MMDBc0029666

Metabolite Identification

Common Name

S-Acetyldihydrolipoamide

Description

S-acetyldihydrolipoamide is a member of the chemical class known as N-acyl Amines. These are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. In E. coli the dihydrolipoyl transacetylase component (E2) of the pyruvate dehydrogenase complex catalyzes the reaction of acetyl coenzyme A (acetyl-CoA) with dihydrolipoamide, producing coenzyme A and S-acetyldihydrolipoamide. [PMID: 3101735 ]

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>
MMDBc0029666

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₀H₁₉NO₂S₂

Average Mass

249.393

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191720	Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial	Enzyme	P08559	Homo sapiens
MMDBp0194147	Dihydrolipoamide S-acetyltransferase	Enzyme	Q86YI5	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018856	Dihydrolipoamide	S-Acetyldihydrolipoamide	Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex	Dehydrogenation	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	7	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	146	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	242	Human feces; Human ; Human subgingival plaque; Cattle ; Human saliva	Metabolic reconstruction
Bacteria	Actinobacteria	11	Human feces; Human ; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	36	Human feces; Human ; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	65	Human feces; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Firmicutes	12	Human feces; Human ; Human subgingival plaque; Cattle ; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	5	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0001526

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

References

Synthesis Reference

Not Available

General References

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 ]
Yang YS, Frey PA: Dihydrolipoyl transacetylase of Escherichia coli. Formation of 8-S-acetyldihydrolipoamide. Biochemistry. 1986 Dec 16;25(25):8173-8. doi: 10.1021/bi00373a008. [PubMed:3101735 ]
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 ]

Showing metabocard for S-Acetyldihydrolipoamide (MMDBc0029666)

MOL for #<Metabolite:0x00007f91fa1a0368>

3D MOL for #<Metabolite:0x00007f91fa1a0368>

3D SDF for #<Metabolite:0x00007f91fa1a0368>

3D-SDF for #<Metabolite:0x00007f91fa1a0368>

PDB for #<Metabolite:0x00007f91fa1a0368>

3D PDB for #<Metabolite:0x00007f91fa1a0368>

SMILES for #<Metabolite:0x00007f91fa1a0368>

INCHI for #<Metabolite:0x00007f91fa1a0368>

Structure for #<Metabolite:0x00007f91fa1a0368>

3D Structure for #<Metabolite:0x00007f91fa1a0368>