MiMeDB: Showing metabocard for S-(3-Methylbutanoyl)-dihydrolipoamide-E (MMDBc0047957)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:18:53 UTC

Update Date

2022-09-01 02:13:16 UTC

Metabolite ID

MMDBc0047957

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>
MMDBc0047957

> <DATABASE_NAME>
MIME

> <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

Synonyms

Value	Source
S-(3-Methylbutanoyl)-dihydrolipoamide	ChEBI
S-(3-Methylbutanoyl)dihydrolipoyllysine	HMDB
[Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase]	HMDB

Molecular Formula

C₁₃H₂₅NO₂S₂

Average Mass

291.473

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

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

Biological Properties

Cellular Locations

Membrane

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
MMDBp0191969	2-oxoisovalerate dehydrogenase subunit beta, mitochondrial	Enzyme	P21953	Homo sapiens
MMDBp0191970	2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial	Unknown	P12694	Homo sapiens
MMDBp0193802	Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial	Enzyme	P11182	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0002530	Ketoleucine	Carbon dioxide	Branched chain keto acid dehydrogenase e1, alpha polypeptide	4-Methyl-2-Oxopentanoate:[Dihydrolipoyllysine-Residue (2-Methylpropanoyl)Transferase] Lipoyllysine 2-Oxidoreductase (Decarboxylating, Acceptor-2-Methylpropanoylating)	VMH	11839747 12387880 15576032
MMDBr0002652	Coenzyme A	Dihydrolipoamide	Dihydrolipoamide branched chain transacylase e2	3-Methylbutanoyl Coenzyme A:Enzyme N6- (Dihydrolipoyl)Lysine S- (3-Methylbutanoyl)Transferase Valine, Leucine And Isoleucine Degradation	VMH	1943690
MMDBr0008358	3-Methyl-1-hydroxybutyl-TPP	S-(3-Methylbutanoyl)-dihydrolipoamide-E	Not Available	LPAMMBT	VMH	30371894

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	36	Human feces; Human sputum; Human ; Human pleural fluid plaque	Metabolic reconstruction
Bacteria	Firmicutes	93	Human feces; Human ; Human sputum; Human saliva; Human urine; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	13	Human feces; Human	Metabolic reconstruction
Bacteria	Bacteroidetes	8	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	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

HMDB0006867

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

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for S-(3-Methylbutanoyl)-dihydrolipoamide-E (MMDBc0047957)

MOL for #<Metabolite:0x000055c79c1f4528>

3D MOL for #<Metabolite:0x000055c79c1f4528>

3D SDF for #<Metabolite:0x000055c79c1f4528>

3D-SDF for #<Metabolite:0x000055c79c1f4528>

PDB for #<Metabolite:0x000055c79c1f4528>

3D PDB for #<Metabolite:0x000055c79c1f4528>

SMILES for #<Metabolite:0x000055c79c1f4528>

INCHI for #<Metabolite:0x000055c79c1f4528>

Structure for #<Metabolite:0x000055c79c1f4528>

3D Structure for #<Metabolite:0x000055c79c1f4528>