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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-08-13 17:12:07 UTC

Update Date

2021-09-14 14:57:29 UTC

HMDB ID

HMDB0006867

Secondary Accession Numbers

HMDB06867

Metabolite Identification

Common Name

S-(3-Methylbutanoyl)-dihydrolipoamide-E

Description

S-(3-Methylbutanoyl)-dihydrolipoamide-E is an intermediate in valine, leucine and isoleucine degradation(KEGG ID C15975 ). It is the second to last step in the synthesis of branched chain fatty acid and is converted from 3-methyl-hydroxybutyl-ThPP via the enzyme 2-oxoisovalerate dehydrogenase [EC:1.2.4.4]. It is then converted to 3-methylbutanoyl-CoA via the enzyme dihydrolipoyllysine-residue (2-methylpropanoyl)transferase[EC:2.3.1.168].

Structure

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

HMDB0006867
     RDKit          3D
S-(3-Methylbutanoyl)-dihydrolipoamide-E
 43 42  0  0  0  0  0  0  0  0999 V2000
    5.1057    0.8275   -1.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8539    1.6469    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6142    2.9744    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4089    1.9884    0.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5076    0.8414    0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9164   -0.2949    0.4218 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7609    1.1095    0.6925 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1660   -0.4366    0.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449   -1.2210   -0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401   -2.4889   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1540   -3.4478    1.0718 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3922   -2.2384    0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0480   -1.4689   -1.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5024   -1.1975   -0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7780   -0.4012    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1719    0.9430    0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1713    1.8257    1.4886 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6404    1.3727   -0.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4176    1.0830   -1.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0776   -0.2499   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1795    1.0147   -1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2401    1.0573    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7513    3.2066   -0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5655    2.9423    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0091    3.7805    0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820    2.5928   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    2.6939    1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968   -0.1769    1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393   -1.0723    1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905   -1.5468   -0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -0.6767   -1.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8828   -3.1268   -1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9667   -4.5085    1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435   -1.6911    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726   -3.2397    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388   -2.0987   -2.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5431   -0.5216   -1.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0800   -2.1662   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8895   -0.6770   -1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3666   -0.8916    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8853   -0.2898    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0211    2.3048    1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2351    1.9235    1.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  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
  3 23  1  0
  3 24  1  0
  3 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  0  0            999 V2000
   12.4343   -4.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1454   -4.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7231   -4.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4343   -3.3644    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.8565   -4.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0121   -4.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6094   -4.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0121   -3.3644    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.3204   -4.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0315   -4.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0315   -5.4558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8263   -4.2010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3010   -2.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5899   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788   -2.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3010   -2.1095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1677   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8788   -2.1095    0.0000 C   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
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006867

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
KMUSXGCRMMQDBP-UHFFFAOYSA-N

> <FORMULA>
C13H25NO2S2

> <MOLECULAR_WEIGHT>
291.473

> <EXACT_MASS>
291.132670429

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.88628635156876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[(3-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
2.6685916873333335

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.64136740256065

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.059200822546359

> <JCHEM_PKA_STRONGEST_BASIC>
-0.579109915468308

> <JCHEM_POLAR_SURFACE_AREA>
60.160000000000004

> <JCHEM_REFRACTIVITY>
81.0031

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(3-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006867
     RDKit          3D
S-(3-Methylbutanoyl)-dihydrolipoamide-E
 43 42  0  0  0  0  0  0  0  0999 V2000
    5.1057    0.8275   -1.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8539    1.6469    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6142    2.9744    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4089    1.9884    0.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5076    0.8414    0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9164   -0.2949    0.4218 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7609    1.1095    0.6925 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1660   -0.4366    0.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449   -1.2210   -0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401   -2.4889   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1540   -3.4478    1.0718 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3922   -2.2384    0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0480   -1.4689   -1.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5024   -1.1975   -0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7780   -0.4012    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1719    0.9430    0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1713    1.8257    1.4886 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6404    1.3727   -0.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4176    1.0830   -1.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0776   -0.2499   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1795    1.0147   -1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2401    1.0573    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7513    3.2066   -0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5655    2.9423    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0091    3.7805    0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820    2.5928   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    2.6939    1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968   -0.1769    1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393   -1.0723    1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905   -1.5468   -0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -0.6767   -1.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8828   -3.1268   -1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9667   -4.5085    1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435   -1.6911    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726   -3.2397    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388   -2.0987   -2.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5431   -0.5216   -1.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0800   -2.1662   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8895   -0.6770   -1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3666   -0.8916    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8853   -0.2898    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0211    2.3048    1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2351    1.9235    1.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  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
  3 23  1  0
  3 24  1  0
  3 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      23.211  -7.842   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.538  -8.623   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.883  -8.623   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      23.211  -6.280   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0      25.865  -7.842   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.556  -7.842   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.271  -8.623   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0      20.556  -6.280   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0      28.598  -7.842   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.925  -8.623   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      29.925 -10.184   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      31.409  -7.842   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      19.229  -5.499   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.901  -6.280   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.574  -5.499   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      19.229  -3.938   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.246  -6.280   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.574  -3.938   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1                                                            
CONECT    5    2    7                                                       
CONECT    6    3    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   13                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   17   18                                                  
CONECT   16   13                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0006867
HETATM    1  C1  UNL     1       5.106   0.828  -1.066  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.854   1.647   0.191  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.614   2.974   0.091  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.409   1.988   0.365  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.508   0.841   0.475  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.916  -0.295   0.422  1.00  0.00           O  
HETATM    7  S1  UNL     1       0.761   1.110   0.693  1.00  0.00           S  
HETATM    8  C6  UNL     1      -0.166  -0.437   0.808  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.145  -1.221  -0.483  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.940  -2.489  -0.279  1.00  0.00           C  
HETATM   11  S2  UNL     1      -0.154  -3.448   1.072  1.00  0.00           S  
HETATM   12  C9  UNL     1      -2.392  -2.238   0.049  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.048  -1.469  -1.083  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.502  -1.198  -0.798  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.778  -0.401   0.423  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.172   0.943   0.343  1.00  0.00           C  
HETATM   17  N1  UNL     1      -4.171   1.826   1.489  1.00  0.00           N  
HETATM   18  O2  UNL     1      -3.640   1.373  -0.706  1.00  0.00           O  
HETATM   19  H1  UNL     1       4.418   1.083  -1.877  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.078  -0.250  -0.784  1.00  0.00           H  
HETATM   21  H3  UNL     1       6.180   1.015  -1.365  1.00  0.00           H  
HETATM   22  H4  UNL     1       5.240   1.057   1.045  1.00  0.00           H  
HETATM   23  H5  UNL     1       5.751   3.207  -0.986  1.00  0.00           H  
HETATM   24  H6  UNL     1       6.565   2.942   0.654  1.00  0.00           H  
HETATM   25  H7  UNL     1       5.009   3.781   0.552  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.082   2.593  -0.523  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.334   2.694   1.226  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.197  -0.177   1.061  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.339  -1.072   1.570  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.890  -1.547  -0.743  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.523  -0.677  -1.351  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.883  -3.127  -1.181  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.967  -4.508   1.463  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.544  -1.691   0.977  1.00  0.00           H  
HETATM   35  H17 UNL     1      -2.873  -3.240   0.143  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.939  -2.099  -2.017  1.00  0.00           H  
HETATM   37  H19 UNL     1      -2.543  -0.522  -1.280  1.00  0.00           H  
HETATM   38  H20 UNL     1      -5.080  -2.166  -0.751  1.00  0.00           H  
HETATM   39  H21 UNL     1      -4.889  -0.677  -1.721  1.00  0.00           H  
HETATM   40  H22 UNL     1      -4.367  -0.892   1.327  1.00  0.00           H  
HETATM   41  H23 UNL     1      -5.885  -0.290   0.571  1.00  0.00           H  
HETATM   42  H24 UNL     1      -5.021   2.305   1.804  1.00  0.00           H  
HETATM   43  H25 UNL     1      -3.235   1.924   1.952  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   22
CONECT    3   23   24   25
CONECT    4    5   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

HMDB0006867
     RDKit          3D
S-(3-Methylbutanoyl)-dihydrolipoamide-E
 43 42  0  0  0  0  0  0  0  0999 V2000
    5.1057    0.8275   -1.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8539    1.6469    0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6142    2.9744    0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4089    1.9884    0.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5076    0.8414    0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9164   -0.2949    0.4218 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7609    1.1095    0.6925 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1660   -0.4366    0.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449   -1.2210   -0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401   -2.4889   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1540   -3.4478    1.0718 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3922   -2.2384    0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0480   -1.4689   -1.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5024   -1.1975   -0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7780   -0.4012    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1719    0.9430    0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1713    1.8257    1.4886 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6404    1.3727   -0.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4176    1.0830   -1.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0776   -0.2499   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1795    1.0147   -1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2401    1.0573    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7513    3.2066   -0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5655    2.9423    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0091    3.7805    0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820    2.5928   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339    2.6939    1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968   -0.1769    1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393   -1.0723    1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905   -1.5468   -0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227   -0.6767   -1.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8828   -3.1268   -1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9667   -4.5085    1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435   -1.6911    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8726   -3.2397    0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388   -2.0987   -2.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5431   -0.5216   -1.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0800   -2.1662   -0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8895   -0.6770   -1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3666   -0.8916    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8853   -0.2898    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0211    2.3048    1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2351    1.9235    1.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  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
  3 23  1  0
  3 24  1  0
  3 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-(3-Methylbutanoyl)-dihydrolipoamide	ChEBI
S-(3-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-[(3-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide

Traditional Name

8-[(3-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

KMUSXGCRMMQDBP-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:27462 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006867)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006867)

Source

Endogenous

Endogenous (HMDB: HMDB0006867)

Animal

Animal (HMDB: HMDB0006867)

Exogenous

Food

Food (HMDB: HMDB0006867)

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: HMDB0006867)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006867)
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: HMDB0006867)

Biochemical process

Lipid transport (HMDB: HMDB0006867)

Role

Biological role

Energy source (HMDB: HMDB0006867)

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	0.011 g/L	ALOGPS
logP	3.35	ALOGPS
logP	2.67	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 m³·mol⁻¹	ChemAxon
Polarizability	33.89 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]+	170.416	31661259
DarkChem	[M-H]-	164.341	31661259
DeepCCS	[M+H]+	168.612	30932474
DeepCCS	[M-H]-	165.949	30932474
DeepCCS	[M-2H]-	201.333	30932474
DeepCCS	[M+Na]+	177.427	30932474
AllCCS	[M+H]+	168.7	32859911
AllCCS	[M+H-H2O]+	166.0	32859911
AllCCS	[M+NH4]+	171.2	32859911
AllCCS	[M+Na]+	172.0	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	172.9	32859911
AllCCS	[M+HCOO]-	174.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-(3-Methylbutanoyl)-dihydrolipoamide-E	CC(C)CC(=O)SCCC(S)CCCCC(N)=O	3487.3	Standard polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E	CC(C)CC(=O)SCCC(S)CCCCC(N)=O	2122.8	Standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E	CC(C)CC(=O)SCCC(S)CCCCC(N)=O	2447.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C	2485.6	Semi standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C	2351.7	Standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C	3712.1	Standard polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C	2483.7	Semi standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C	2326.4	Standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C	3110.8	Standard polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C	2537.2	Semi standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C	2537.6	Standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C	2974.5	Standard polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2514.9	Semi standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2441.3	Standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	3045.0	Standard polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C	2602.4	Semi standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C	2632.4	Standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C	2757.1	Standard polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C	2741.3	Semi standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C	2584.2	Standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C	3682.0	Standard polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C	2714.7	Semi standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C	2536.5	Standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,1TBDMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C	3179.9	Standard polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	3035.3	Semi standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2908.1	Standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #1	CC(C)CC(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	3058.4	Standard polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2996.7	Semi standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2826.7	Standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,2TBDMS,isomer #2	CC(C)CC(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3168.7	Standard polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TBDMS,isomer #1	CC(C)CC(=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	3325.8	Semi standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TBDMS,isomer #1	CC(C)CC(=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	3146.4	Standard non polar	33892256
S-(3-Methylbutanoyl)-dihydrolipoamide-E,3TBDMS,isomer #1	CC(C)CC(=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	3002.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9330000000-7645e890a76a3a061254	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 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-(3-Methylbutanoyl)-dihydrolipoamide-E 10V, Positive-QTOF	splash10-0adl-1590000000-73c597c9ff41eaa096da	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 20V, Positive-QTOF	splash10-05bo-9860000000-959ec4437326b233f8c5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 40V, Positive-QTOF	splash10-0r03-8900000000-a1e7f4573030a9fe253d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 10V, Negative-QTOF	splash10-0abc-3290000000-451e0e77862833c4f8a0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 20V, Negative-QTOF	splash10-05al-9460000000-643c13495fbd0a3ab1fd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 40V, Negative-QTOF	splash10-000x-9100000000-be2cd4708826cfbabdff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 10V, Negative-QTOF	splash10-0006-0090000000-d3adc271f810363a2afc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 20V, Negative-QTOF	splash10-0avi-3960000000-19b3ed40b33008867234	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 40V, Negative-QTOF	splash10-0006-9000000000-179d1961f85de3e54022	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 10V, Positive-QTOF	splash10-052f-0290000000-2ee95e606494ba3b1dc0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 20V, Positive-QTOF	splash10-05ai-2790000000-dd330a5aa1d579c5bdd5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methylbutanoyl)-dihydrolipoamide-E 40V, Positive-QTOF	splash10-000i-9500000000-dae67f00fee8e6329c5f	2021-09-24	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

FDB024123

KNApSAcK ID

Not Available

Chemspider ID

389466

KEGG Compound ID

C05119

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440566

PDB ID

Not Available

ChEBI ID

27462

Food Biomarker Ontology

Not Available

VMH ID

HC01377

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-(3-Methylbutanoyl)-dihydrolipoamide-E (HMDB0006867)

MOL for HMDB0006867 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

3D MOL for HMDB0006867 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

3D SDF for HMDB0006867 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

3D-SDF for HMDB0006867 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

PDB for HMDB0006867 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

3D PDB for HMDB0006867 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

SMILES for HMDB0006867 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

INCHI for HMDB0006867 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

Structure for HMDB0006867 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

3D Structure for HMDB0006867 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes