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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-08-13 17:20:38 UTC

Update Date

2021-09-14 15:43:42 UTC

HMDB ID

HMDB0006869

Secondary Accession Numbers

HMDB06869

Metabolite Identification

Common Name

S-(2-Methylbutanoyl)-dihydrolipoamide

Description

S-(2-Methylbutanoyl)-dihydrolipoamide-E is an intermediate in isoleucine degradation. S-(2-Methylbutanoyl)-dihydrolipoamide is normally conjugated to a lysine residue of the methylpropanoyltransferase enzyme (E stands for enzyme). The structure shown here is the free form. Specifically S-(2-Methylbutanoyl)-dihydrolipoamide-E is the 2-methylbutanoyl thioester of the reduced lipoyllysine residue in dihydrolipoyllysine-residue (2-methylpropanoyl)transferase.

Structure

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

HMDB0006869
     RDKit          3D
S-(2-Methylbutanoyl)-dihydrolipoamide
 43 42  0  0  0  0  0  0  0  0999 V2000
    5.9256   -0.4644   -0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -0.6266   -1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278    0.0883   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    1.5549   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4099   -0.5819    0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423   -1.5711    0.9205 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480   -0.1585    2.0688 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935    1.2370    1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2257    1.0302    0.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044   -0.1075    1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -1.6661    1.3197 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8616   -0.1553    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067   -1.2667    0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9623   -1.3457   -0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7293   -0.0694   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8998   -0.0968   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7056    1.0525   -1.4144 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1849   -1.0938   -2.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7037    0.0415   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7925    0.1261    0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3623   -1.4422   -0.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3890   -1.6911   -1.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6726   -0.1139   -2.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546   -0.0047   -1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895    2.2055   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8039    1.7600   -1.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1462    1.8252    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423    2.1022    1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698    1.5025    2.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3981    1.9782    0.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5654    0.9327   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1195    0.1871    2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0575   -2.5092    0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4740   -0.2912   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687    0.8249    0.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718   -2.2340    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1600   -1.0405    1.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6710   -2.1613   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5907   -1.5915   -1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1767    0.0371    0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1646    0.8412   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8467    1.5287   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1610    1.4272   -0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
M  END


  Mrv0541 02231220542D          

 18 17  0  0  1  0            999 V2000
    4.4688   -8.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1970   -8.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8970   -8.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6251   -8.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3251   -8.5265    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0532   -8.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7532   -8.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4814   -8.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1813   -8.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9095   -8.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6095   -8.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3376   -8.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0376   -8.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8688   -9.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6533   -7.2653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5096   -7.3628    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.7658   -8.3338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0095   -9.5461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  1  0  0  0
 15  4  2  0  0  0  0
 16  8  1  0  0  0  0
 17 13  1  0  0  0  0
 18 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006869

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)C(=O)SCCC(S)CCCCC(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H25NO2S2/c1-3-10(2)13(16)18-9-8-11(17)6-4-5-7-12(14)15/h10-11,17H,3-9H2,1-2H3,(H2,14,15)

> <INCHI_KEY>
UFNCWFSSEGPJNL-UHFFFAOYSA-N

> <FORMULA>
C13H25NO2S2

> <MOLECULAR_WEIGHT>
291.473

> <EXACT_MASS>
291.132670429

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.50074662210743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[(2-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide

> <ALOGPS_LOGP>
3.67

> <JCHEM_LOGP>
2.9245588693333335

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.640352941214918

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.059200810272236

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5791100140301085

> <JCHEM_POLAR_SURFACE_AREA>
60.160000000000004

> <JCHEM_REFRACTIVITY>
81.02899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(2-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006869
     RDKit          3D
S-(2-Methylbutanoyl)-dihydrolipoamide
 43 42  0  0  0  0  0  0  0  0999 V2000
    5.9256   -0.4644   -0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -0.6266   -1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278    0.0883   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    1.5549   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4099   -0.5819    0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423   -1.5711    0.9205 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480   -0.1585    2.0688 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935    1.2370    1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2257    1.0302    0.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044   -0.1075    1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -1.6661    1.3197 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8616   -0.1553    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067   -1.2667    0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9623   -1.3457   -0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7293   -0.0694   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8998   -0.0968   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7056    1.0525   -1.4144 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1849   -1.0938   -2.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7037    0.0415   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7925    0.1261    0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3623   -1.4422   -0.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3890   -1.6911   -1.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6726   -0.1139   -2.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546   -0.0047   -1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895    2.2055   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8039    1.7600   -1.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1462    1.8252    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423    2.1022    1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698    1.5025    2.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3981    1.9782    0.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5654    0.9327   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1195    0.1871    2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0575   -2.5092    0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4740   -0.2912   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687    0.8249    0.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718   -2.2340    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1600   -1.0405    1.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6710   -2.1613   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5907   -1.5915   -1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1767    0.0371    0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1646    0.8412   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8467    1.5287   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1610    1.4272   -0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  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       8.342 -15.734   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.701 -15.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.008 -15.825   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.367 -15.101   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0      13.674 -15.916   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0      15.033 -15.192   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.339 -16.007   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.699 -15.283   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.005 -16.098   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.364 -15.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.671 -16.189   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.030 -15.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.337 -16.280   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.955 -17.364   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.419 -13.562   0.000  0.00  0.00           O+0
HETATM   16  S   UNK     0      17.751 -13.744   0.000  0.00  0.00           S+0
HETATM   17  N   UNK     0      25.696 -15.556   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      24.284 -17.819   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   17   18                                                  
CONECT   14    3                                                            
CONECT   15    4                                                            
CONECT   16    8                                                            
CONECT   17   13                                                            
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0006869
HETATM    1  C1  UNL     1       5.926  -0.464  -0.654  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.621  -0.627  -1.377  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.528   0.088  -0.573  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.875   1.555  -0.452  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.410  -0.582   0.727  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.142  -1.571   0.921  1.00  0.00           O  
HETATM    7  S1  UNL     1       2.348  -0.158   2.069  1.00  0.00           S  
HETATM    8  C6  UNL     1       1.293   1.237   1.750  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.226   1.030   0.721  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.704  -0.107   1.131  1.00  0.00           C  
HETATM   11  S2  UNL     1       0.155  -1.666   1.320  1.00  0.00           S  
HETATM   12  C9  UNL     1      -1.862  -0.155   0.158  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.807  -1.267   0.526  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.962  -1.346  -0.428  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.729  -0.069  -0.407  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.900  -0.097  -1.335  1.00  0.00           C  
HETATM   17  N1  UNL     1      -6.706   1.053  -1.414  1.00  0.00           N  
HETATM   18  O2  UNL     1      -6.185  -1.094  -2.035  1.00  0.00           O  
HETATM   19  H1  UNL     1       6.704   0.042  -1.286  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.793   0.126   0.264  1.00  0.00           H  
HETATM   21  H3  UNL     1       6.362  -1.442  -0.359  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.389  -1.691  -1.445  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.673  -0.114  -2.357  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.555  -0.005  -1.109  1.00  0.00           H  
HETATM   25  H7  UNL     1       3.089   2.206  -0.886  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.804   1.760  -1.050  1.00  0.00           H  
HETATM   27  H9  UNL     1       4.146   1.825   0.589  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.942   2.102   1.464  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.770   1.503   2.709  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.398   1.978   0.749  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.565   0.933  -0.314  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.120   0.187   2.120  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.058  -2.509   0.215  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.474  -0.291  -0.868  1.00  0.00           H  
HETATM   35  H17 UNL     1      -2.369   0.825   0.229  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.272  -2.234   0.616  1.00  0.00           H  
HETATM   37  H19 UNL     1      -3.160  -1.041   1.571  1.00  0.00           H  
HETATM   38  H20 UNL     1      -4.671  -2.161  -0.172  1.00  0.00           H  
HETATM   39  H21 UNL     1      -3.591  -1.592  -1.447  1.00  0.00           H  
HETATM   40  H22 UNL     1      -5.177   0.037   0.619  1.00  0.00           H  
HETATM   41  H23 UNL     1      -4.165   0.841  -0.637  1.00  0.00           H  
HETATM   42  H24 UNL     1      -6.847   1.529  -2.320  1.00  0.00           H  
HETATM   43  H25 UNL     1      -7.161   1.427  -0.567  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4    5   24
CONECT    4   25   26   27
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   28   29
CONECT    9   10   30   31
CONECT   10   11   12   32
CONECT   11   33
CONECT   12   13   34   35
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16   40   41
CONECT   16   17   18   18
CONECT   17   42   43
END

HMDB0006869
     RDKit          3D
S-(2-Methylbutanoyl)-dihydrolipoamide
 43 42  0  0  0  0  0  0  0  0999 V2000
    5.9256   -0.4644   -0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -0.6266   -1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278    0.0883   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    1.5549   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4099   -0.5819    0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423   -1.5711    0.9205 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480   -0.1585    2.0688 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935    1.2370    1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2257    1.0302    0.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044   -0.1075    1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -1.6661    1.3197 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8616   -0.1553    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067   -1.2667    0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9623   -1.3457   -0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7293   -0.0694   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8998   -0.0968   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7056    1.0525   -1.4144 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1849   -1.0938   -2.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7037    0.0415   -1.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7925    0.1261    0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3623   -1.4422   -0.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3890   -1.6911   -1.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6726   -0.1139   -2.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546   -0.0047   -1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895    2.2055   -0.8856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8039    1.7600   -1.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1462    1.8252    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423    2.1022    1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698    1.5025    2.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3981    1.9782    0.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5654    0.9327   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1195    0.1871    2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0575   -2.5092    0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4740   -0.2912   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687    0.8249    0.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2718   -2.2340    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1600   -1.0405    1.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6710   -2.1613   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5907   -1.5915   -1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1767    0.0371    0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1646    0.8412   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8467    1.5287   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1610    1.4272   -0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
S-(2-Methylbutanoyl)dihydrolipoyllysine	HMDB
[Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase]	HMDB

Chemical Formula

C₁₃H₂₅NO₂S₂

Average Molecular Weight

291.473

Monoisotopic Molecular Weight

291.132670429

IUPAC Name

8-[(2-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide

Traditional Name

8-[(2-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)SCCC(S)CCCCC(N)=O

InChI Identifier

InChI=1S/C13H25NO2S2/c1-3-10(2)13(16)18-9-8-11(17)6-4-5-7-12(14)15/h10-11,17H,3-9H2,1-2H3,(H2,14,15)

InChI Key

UFNCWFSSEGPJNL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl thioesters. These are thioester derivatives of a fatty acid with the general formula RC(=O)SR', where R is the fatty acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Fatty acyl thioesters

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

S-(methylbutanoyl)dihydrolipoamide (CHEBI:28692 )
a small molecule (CPD-941 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006869)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006869)

Source

Endogenous

Endogenous (HMDB: HMDB0006869)

Animal

Animal (HMDB: HMDB0006869)

Exogenous

Food

Food (HMDB: HMDB0006869)

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)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006869)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006869)
Valine, Leucine, and Isoleucine Degradation (PathBank: SMP0063689)

Disease pathway

2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120439)
Methylmalonate Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120523)
Isovaleric Acidemia (PathBank: SMP0120589)
3-Methylglutaconic Aciduria Type I (PathBank: SMP0120663)
Beta-Ketothiolase Deficiency (PathBank: SMP0120679)
3-Hydroxyisobutyric Aciduria (PathBank: SMP0120806)
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I (PathBank: SMP0120441)
3-Methylglutaconic Aciduria Type IV (PathBank: SMP0120444)
Methylmalonic Aciduria (PathBank: SMP0120525)
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency (PathBank: SMP0120661)
3-Methylglutaconic Aciduria Type III (PathBank: SMP0120664)
Maple Syrup Urine Disease (PathBank: SMP0120516)
Propionic Acidemia (PathBank: SMP0120537)
Isobutyryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120588)
Isovaleric Aciduria (PathBank: SMP0120723)
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency (PathBank: SMP0120586)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0000137)

Lipid metabolism pathway (HMDB: HMDB0006869)

Biochemical process

Lipid transport (HMDB: HMDB0006869)

Role

Biological role

Energy source (HMDB: HMDB0006869)

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	0.01 g/L	ALOGPS
logP	3.67	ALOGPS
logP	2.92	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	10.06	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	11	ChemAxon
Refractivity	81.03 m³·mol⁻¹	ChemAxon
Polarizability	33.5 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]+	168.508	31661259
DarkChem	[M-H]-	166.216	31661259
DeepCCS	[M+H]+	168.434	30932474
DeepCCS	[M-H]-	166.076	30932474
DeepCCS	[M-2H]-	200.51	30932474
DeepCCS	[M+Na]+	176.525	30932474
AllCCS	[M+H]+	168.9	32859911
AllCCS	[M+H-H2O]+	166.1	32859911
AllCCS	[M+NH4]+	171.4	32859911
AllCCS	[M+Na]+	172.1	32859911
AllCCS	[M-H]-	171.6	32859911
AllCCS	[M+Na-2H]-	172.9	32859911
AllCCS	[M+HCOO]-	174.5	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.	6.27 minutes	32390414
Predicted by Siyang on May 30, 2022	16.0273 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2591.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	430.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	185.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	216.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	636.1 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	741.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1337.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	469.6 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	1504.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	301.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	418.7 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	32.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-(2-Methylbutanoyl)-dihydrolipoamide	CCC(C)C(=O)SCCC(S)CCCCC(N)=O	3427.9	Standard polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide	CCC(C)C(=O)SCCC(S)CCCCC(N)=O	2142.4	Standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide	CCC(C)C(=O)SCCC(S)CCCCC(N)=O	2457.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-(2-Methylbutanoyl)-dihydrolipoamide,1TMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C	2519.4	Semi standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,1TMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C	2383.5	Standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,1TMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C	3682.0	Standard polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,1TMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C	2495.8	Semi standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,1TMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C	2344.1	Standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,1TMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C	3113.6	Standard polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C	2567.7	Semi standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C	2558.5	Standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C	2974.6	Standard polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2540.2	Semi standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2455.1	Standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	3046.0	Standard polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,3TMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C	2652.4	Semi standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,3TMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C	2650.1	Standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,3TMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C	2775.9	Standard polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,1TBDMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C	2774.6	Semi standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,1TBDMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C	2612.7	Standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,1TBDMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C	3652.7	Standard polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,1TBDMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C	2743.3	Semi standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,1TBDMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C	2553.6	Standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,1TBDMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C	3179.8	Standard polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TBDMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	3082.5	Semi standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TBDMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2928.5	Standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TBDMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	3066.1	Standard polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TBDMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3031.3	Semi standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TBDMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2842.8	Standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,2TBDMS,isomer #2	CCC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3170.2	Standard polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,3TBDMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	3381.8	Semi standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,3TBDMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	3171.1	Standard non polar	33892256
S-(2-Methylbutanoyl)-dihydrolipoamide,3TBDMS,isomer #1	CCC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	3015.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9440000000-877a8908188a4b9ebf15	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 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-(2-Methylbutanoyl)-dihydrolipoamide 10V, Positive-QTOF	splash10-05ox-1590000000-8990b01bec1542bc8685	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 20V, Positive-QTOF	splash10-0a70-6950000000-ec727734be57f42cd429	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 40V, Positive-QTOF	splash10-0a4i-9600000000-66cf65ecaa53c1f3c282	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 10V, Negative-QTOF	splash10-0ab9-4590000000-2a509e71418cfb3b6499	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 20V, Negative-QTOF	splash10-0ac3-9680000000-907d9cdccee37b33c93c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 40V, Negative-QTOF	splash10-0006-9100000000-c6f4b7f06ed078762276	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 10V, Positive-QTOF	splash10-0006-0190000000-64102de5dbea75355e97	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 20V, Positive-QTOF	splash10-00a6-2940000000-98da17f6a6690d13a787	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 40V, Positive-QTOF	splash10-059i-9400000000-370f86855cf150dcc798	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 10V, Negative-QTOF	splash10-0006-0090000000-431d68145b7602d0fba0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 20V, Negative-QTOF	splash10-0avi-1940000000-95224a4cc03836a7327f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(2-Methylbutanoyl)-dihydrolipoamide 40V, Negative-QTOF	splash10-0006-9100000000-bf3e84c89d49f43b8761	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Valine, leucine and isoleucine degradation	Not Available
Beta-Ketothiolase Deficiency		Not Available
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency		Not Available
Propionic Acidemia		Not Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency		Not Available

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

FDB024125

KNApSAcK ID

Not Available

Chemspider ID

389465

KEGG Compound ID

C05118

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440565

PDB ID

Not Available

ChEBI ID

28692

Food Biomarker Ontology

Not Available

VMH ID

HC01376

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial

General function:: Involved in catalytic activity
Specific function:: The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:: BCKDHB
Uniprot ID:: P21953
Molecular weight:: 43122.065

Enzyme Details

2. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:: The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:: BCKDHA
Uniprot ID:: P12694
Molecular weight:: 50470.58

Enzyme Details

3. Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial

General function:: Involved in acyltransferase activity
Specific function:: The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:: DBT
Uniprot ID:: P11182
Molecular weight:: 53486.635

Showing metabocard for S-(2-Methylbutanoyl)-dihydrolipoamide (HMDB0006869)

MOL for HMDB0006869 (S-(2-Methylbutanoyl)-dihydrolipoamide)

3D MOL for HMDB0006869 (S-(2-Methylbutanoyl)-dihydrolipoamide)

3D SDF for HMDB0006869 (S-(2-Methylbutanoyl)-dihydrolipoamide)

3D-SDF for HMDB0006869 (S-(2-Methylbutanoyl)-dihydrolipoamide)

PDB for HMDB0006869 (S-(2-Methylbutanoyl)-dihydrolipoamide)

3D PDB for HMDB0006869 (S-(2-Methylbutanoyl)-dihydrolipoamide)

SMILES for HMDB0006869 (S-(2-Methylbutanoyl)-dihydrolipoamide)

INCHI for HMDB0006869 (S-(2-Methylbutanoyl)-dihydrolipoamide)

Structure for HMDB0006869 (S-(2-Methylbutanoyl)-dihydrolipoamide)

3D Structure for HMDB0006869 (S-(2-Methylbutanoyl)-dihydrolipoamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes