MiMeDB: Showing metabocard for S-(2-Methylpropionyl)-dihydrolipoamide-E (MMDBc0047958)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:18:57 UTC

Update Date

2024-04-30 20:33:49 UTC

Metabolite ID

MMDBc0047958

Metabolite Identification

Common Name

S-(2-Methylpropionyl)-dihydrolipoamide-E

Description

S-(2-Methylpropionyl)-dihydrolipoamide-E is an intermediate in valine, leucine and isoleucine degradation(KEGG ID C15977). It is the second to last step in the synthesis of branched chain fatty acid and is converted from 2-methyl-1-hydroxypropyl-ThPP via the enzyme 2-oxoisovalerate dehydrogenase [EC:1.2.4.4]. It is then converted to isobutyryl-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

HMDB0006868
     RDKit          3D
S-(2-Methylpropionyl)-dihydrolipoamide-E
 40 39  0  0  0  0  0  0  0  0999 V2000
   -3.9412    2.3787   -1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1226    0.9655   -0.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784   -0.0595   -1.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2210    0.7111    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4986    1.6265    0.7223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968   -0.8844    1.1290 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -0.9037    2.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -0.7566    2.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0998   -1.8276    1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767   -1.9022   -0.3503 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3653   -1.6593    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991   -0.3594    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2010   -0.3365    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624    0.9199   -0.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1225    0.8629   -0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    1.9378   -1.4086 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7640   -0.1310   -0.4093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9506    2.3077   -2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9126    2.7579   -1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7303    3.0459   -0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1963    0.8810   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6493   -1.0298   -1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813   -0.2192   -2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0104    0.2489   -2.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -1.8453    3.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -0.0815    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245   -0.8168    3.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4847    0.2211    1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2756   -2.8002    1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886   -3.1222   -0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7385   -2.4728    0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -1.7530    1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033   -0.2461   -0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482    0.5320    0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4150   -1.2263   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350   -0.5101    0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308    1.1123   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363    1.7862    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7156    2.1166   -2.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3998    2.5650   -0.8322 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
M  END


  Mrv0541 02231220542D          

 17 16  0  0  0  0            999 V2000
   12.0735   -4.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7847   -4.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3626   -4.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0735   -3.3718    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.4957   -4.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6515   -4.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2486   -4.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6515   -3.3718    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.9596   -4.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6707   -4.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6707   -5.4632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4654   -4.2084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9404   -2.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -3.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5182   -2.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9404   -2.1170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2292   -4.2237    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
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047958

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H23NO2S2/c1-9(2)12(15)17-8-7-10(16)5-3-4-6-11(13)14/h9-10,16H,3-8H2,1-2H3,(H2,13,14)

> <INCHI_KEY>
UEFURMXXHJCLJP-UHFFFAOYSA-N

> <FORMULA>
C12H23NO2S2

> <MOLECULAR_WEIGHT>
277.447

> <EXACT_MASS>
277.117020365

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.12260650241717

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.4799902043333333

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.640445216657476

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.059200810345372

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5791100055119881

> <JCHEM_POLAR_SURFACE_AREA>
60.160000000000004

> <JCHEM_REFRACTIVITY>
76.42800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006868
     RDKit          3D
S-(2-Methylpropionyl)-dihydrolipoamide-E
 40 39  0  0  0  0  0  0  0  0999 V2000
   -3.9412    2.3787   -1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1226    0.9655   -0.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784   -0.0595   -1.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2210    0.7111    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4986    1.6265    0.7223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968   -0.8844    1.1290 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -0.9037    2.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -0.7566    2.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0998   -1.8276    1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767   -1.9022   -0.3503 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3653   -1.6593    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991   -0.3594    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2010   -0.3365    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624    0.9199   -0.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1225    0.8629   -0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    1.9378   -1.4086 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7640   -0.1310   -0.4093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9506    2.3077   -2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9126    2.7579   -1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7303    3.0459   -0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1963    0.8810   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6493   -1.0298   -1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813   -0.2192   -2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0104    0.2489   -2.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -1.8453    3.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -0.0815    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245   -0.8168    3.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4847    0.2211    1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2756   -2.8002    1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886   -3.1222   -0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7385   -2.4728    0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -1.7530    1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033   -0.2461   -0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482    0.5320    0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4150   -1.2263   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350   -0.5101    0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308    1.1123   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363    1.7862    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7156    2.1166   -2.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3998    2.5650   -0.8322 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  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      22.537  -7.856   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.865  -8.636   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.210  -8.636   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      22.537  -6.294   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0      25.192  -7.856   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.883  -7.856   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.597  -8.636   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0      19.883  -6.294   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0      27.925  -7.856   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.252  -8.636   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      29.252 -10.198   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      30.735  -7.856   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      18.555  -5.513   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.228  -6.294   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.901  -5.513   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      18.555  -3.952   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      17.228  -7.884   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   17                                                  
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0006868
HETATM    1  C1  UNL     1      -3.941   2.379  -1.334  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.123   0.965  -0.819  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.878  -0.060  -1.900  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.221   0.711   0.335  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.499   1.627   0.722  1.00  0.00           O  
HETATM    6  S1  UNL     1      -3.197  -0.884   1.129  1.00  0.00           S  
HETATM    7  C5  UNL     1      -2.045  -0.904   2.491  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.613  -0.757   2.129  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.100  -1.828   1.226  1.00  0.00           C  
HETATM   10  S2  UNL     1      -0.977  -1.902  -0.350  1.00  0.00           S  
HETATM   11  C8  UNL     1       1.365  -1.659   0.937  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.699  -0.359   0.271  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.201  -0.337   0.047  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.662   0.920  -0.617  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.122   0.863  -0.796  1.00  0.00           C  
HETATM   16  N1  UNL     1       5.800   1.938  -1.409  1.00  0.00           N  
HETATM   17  O2  UNL     1       5.764  -0.131  -0.409  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.951   2.308  -2.443  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.913   2.758  -1.072  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.730   3.046  -0.936  1.00  0.00           H  
HETATM   21  H4  UNL     1      -5.196   0.881  -0.475  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.649  -1.030  -1.385  1.00  0.00           H  
HETATM   23  H6  UNL     1      -4.781  -0.219  -2.529  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.010   0.249  -2.484  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.238  -1.845   3.087  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.335  -0.081   3.195  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.025  -0.817   3.076  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.485   0.221   1.624  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.276  -2.800   1.735  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.589  -3.122  -0.977  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.739  -2.473   0.280  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.934  -1.753   1.886  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.203  -0.246  -0.714  1.00  0.00           H  
HETATM   34  H17 UNL     1       1.448   0.532   0.871  1.00  0.00           H  
HETATM   35  H18 UNL     1       3.415  -1.226  -0.605  1.00  0.00           H  
HETATM   36  H19 UNL     1       3.735  -0.510   0.982  1.00  0.00           H  
HETATM   37  H20 UNL     1       3.131   1.112  -1.583  1.00  0.00           H  
HETATM   38  H21 UNL     1       3.436   1.786   0.057  1.00  0.00           H  
HETATM   39  H22 UNL     1       5.716   2.117  -2.412  1.00  0.00           H  
HETATM   40  H23 UNL     1       6.400   2.565  -0.832  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   21
CONECT    3   22   23   24
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   25   26
CONECT    8    9   27   28
CONECT    9   10   11   29
CONECT   10   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   16   17   17
CONECT   16   39   40
END

HMDB0006868
     RDKit          3D
S-(2-Methylpropionyl)-dihydrolipoamide-E
 40 39  0  0  0  0  0  0  0  0999 V2000
   -3.9412    2.3787   -1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1226    0.9655   -0.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784   -0.0595   -1.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2210    0.7111    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4986    1.6265    0.7223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968   -0.8844    1.1290 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -0.9037    2.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -0.7566    2.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0998   -1.8276    1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767   -1.9022   -0.3503 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3653   -1.6593    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991   -0.3594    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2010   -0.3365    0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624    0.9199   -0.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1225    0.8629   -0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8001    1.9378   -1.4086 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7640   -0.1310   -0.4093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9506    2.3077   -2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9126    2.7579   -1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7303    3.0459   -0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1963    0.8810   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6493   -1.0298   -1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813   -0.2192   -2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0104    0.2489   -2.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -1.8453    3.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -0.0815    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245   -0.8168    3.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4847    0.2211    1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2756   -2.8002    1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886   -3.1222   -0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7385   -2.4728    0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336   -1.7530    1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2033   -0.2461   -0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482    0.5320    0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4150   -1.2263   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350   -0.5101    0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308    1.1123   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4363    1.7862    0.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7156    2.1166   -2.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3998    2.5650   -0.8322 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
M  END

Synonyms

Value	Source
S-(2-Methylpropanoyl)-dihydrolipoamide	ChEBI
S-(2-Methylpropionyl)-dihydrolipoamide	ChEBI
S-(2-Methylpropanoyl)-dihydrolipoamide-e	HMDB
[Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase]S-(2-methylpropanoyl)dihydrolipoyllysine	HMDB

Molecular Formula

C₁₂H₂₃NO₂S₂

Average Mass

277.447

Monoisotopic Mass

277.117020365

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H23NO2S2/c1-9(2)12(15)17-8-7-10(16)5-3-4-6-11(13)14/h9-10,16H,3-8H2,1-2H3,(H2,13,14)

InChI Key

UEFURMXXHJCLJP-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

Fatty amides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

S-substituted dihydrolipoamide (CHEBI:17577 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.48	ChemAxon
logS	-4.2	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	10	ChemAxon
Refractivity	76.43 m³·mol⁻¹	ChemAxon
Polarizability	32.12 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	splash10-006x-9430000000-898ad5ac7f8d34382fce	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0200-1590000000-256cf1b407c15039646a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-7960000000-68678b3f077aeb471401	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k96-9600000000-b142c6b121e61d161a14	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-062c-3590000000-dd8c6dd74f1ee11d43e7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0axu-6790000000-b1e8d0173e84691b6bbb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-ec64c5922fd146f463b0	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0190000000-7ce7db6d296a0c9ccd1c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-044l-3950000000-408139b7c147c5ffb59b	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-007d-9400000000-69ca2ae5bb862cef6baf	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-8ed120c1f1da33069a71	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zmi-2940000000-f72c23450f1a5b08d40c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-daf484d53de0437afb9f	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

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0002529	alpha-Ketoisovaleric acid	S-(2-Methylpropionyl)-dihydrolipoamide-E	branched chain keto acid dehydrogenase E1, alpha polypeptide	VMH	11839747 12387880 15576032
MMDBr0002602	S-(2-Methylpropionyl)-dihydrolipoamide-E	Dihydrolipoamide	dihydrolipoamide branched chain transacylase E2	VMH	10966480 1429740 1943690 7963542
MMDBr0004704	Dihydrolipoamide	S-(2-Methylpropionyl)-dihydrolipoamide-E	branched chain keto acid dehydrogenase E1, beta polypeptide	VMH	2699399 9665099
MMDBr0008354	Dihydrolipoamide	S-(2-Methylpropionyl)-dihydrolipoamide-E	Not Available	VMH	30371894
MMDBr0008360	2-Methyl-1-hydroxypropyl-TPP	S-(2-Methylpropionyl)-dihydrolipoamide-E	Not Available	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	43	Human feces; Human sputum; Human ; Human pleural fluid plaque	Metabolic reconstruction
Bacteria	Actinobacteria	66	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Firmicutes	94	Human feces; Human ; Human sputum; Human saliva; Human urine; Human supragingival plaque; Human subgingival plaque	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

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

HMDB0006868

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024124

KNApSAcK ID

Not Available

Chemspider ID

10128135

KEGG Compound ID

C04424

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11953835

PDB ID

Not Available

ChEBI ID

17577

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-(2-Methylpropionyl)-dihydrolipoamide-E (MMDBc0047958)

MOL for #<Metabolite:0x00007fdb708c0ef8>

3D MOL for #<Metabolite:0x00007fdb708c0ef8>

3D SDF for #<Metabolite:0x00007fdb708c0ef8>

3D-SDF for #<Metabolite:0x00007fdb708c0ef8>

PDB for #<Metabolite:0x00007fdb708c0ef8>

3D PDB for #<Metabolite:0x00007fdb708c0ef8>

SMILES for #<Metabolite:0x00007fdb708c0ef8>

INCHI for #<Metabolite:0x00007fdb708c0ef8>

Structure for #<Metabolite:0x00007fdb708c0ef8>

3D Structure for #<Metabolite:0x00007fdb708c0ef8>