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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-08-13 17:15:34 UTC

Update Date

2021-09-14 15:48:20 UTC

HMDB ID

HMDB0006868

Secondary Accession Numbers

HMDB06868

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>
HMDB0006868

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₁₂H₂₃NO₂S₂

Average Molecular Weight

277.447

Monoisotopic Molecular Weight

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 )

Ontology

Not Available

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	0.016 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	163.854	31661259
DarkChem	[M-H]-	160.503	31661259
DeepCCS	[M+H]+	164.734	30932474
DeepCCS	[M-H]-	162.175	30932474
DeepCCS	[M-2H]-	197.466	30932474
DeepCCS	[M+Na]+	173.393	30932474
AllCCS	[M+H]+	163.7	32859911
AllCCS	[M+H-H2O]+	160.8	32859911
AllCCS	[M+NH4]+	166.4	32859911
AllCCS	[M+Na]+	167.1	32859911
AllCCS	[M-H]-	168.2	32859911
AllCCS	[M+Na-2H]-	169.5	32859911
AllCCS	[M+HCOO]-	171.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.76 minutes	32390414
Predicted by Siyang on May 30, 2022	14.6159 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.96 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2446.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	381.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	193.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	140.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	550.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	682.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1187.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	432.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1370.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	377.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	296.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	398.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	41.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-(2-Methylpropionyl)-dihydrolipoamide-E	CC(C)C(=O)SCCC(S)CCCCC(N)=O	3343.8	Standard polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E	CC(C)C(=O)SCCC(S)CCCCC(N)=O	2018.3	Standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E	CC(C)C(=O)SCCC(S)CCCCC(N)=O	2364.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C	2408.8	Semi standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C	2315.7	Standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C	3594.0	Standard polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C	2376.8	Semi standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C	2268.5	Standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C	3026.2	Standard polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C	2463.0	Semi standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C	2479.1	Standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C)S[Si](C)(C)C	2891.1	Standard polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2434.0	Semi standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2378.8	Standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2955.3	Standard polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,3TMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C	2563.6	Semi standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,3TMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C	2574.5	Standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,3TMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)S[Si](C)(C)C	2691.8	Standard polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TBDMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C	2662.8	Semi standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TBDMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C	2553.3	Standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TBDMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(N)=O)S[Si](C)(C)C(C)(C)C	3567.9	Standard polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TBDMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C	2632.7	Semi standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TBDMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C	2484.8	Standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,1TBDMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N[Si](C)(C)C(C)(C)C	3092.3	Standard polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TBDMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2977.7	Semi standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TBDMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2862.9	Standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TBDMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2980.8	Standard polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TBDMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2937.6	Semi standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TBDMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2778.0	Standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,2TBDMS,isomer #2	CC(C)C(=O)SCCC(S)CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3078.4	Standard polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,3TBDMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	3289.6	Semi standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,3TBDMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	3120.6	Standard non polar	33892256
S-(2-Methylpropionyl)-dihydrolipoamide-E,3TBDMS,isomer #1	CC(C)C(=O)SCCC(CCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2937.0	Standard polar	33892256

Spectra

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

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

VMH ID

2MPDHL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial

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

Enzyme Details

2. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial

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

Enzyme Details

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

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

Showing metabocard for S-(2-Methylpropionyl)-dihydrolipoamide-E (HMDB0006868)

MOL for HMDB0006868 (S-(2-Methylpropionyl)-dihydrolipoamide-E)

3D MOL for HMDB0006868 (S-(2-Methylpropionyl)-dihydrolipoamide-E)

3D SDF for HMDB0006868 (S-(2-Methylpropionyl)-dihydrolipoamide-E)

3D-SDF for HMDB0006868 (S-(2-Methylpropionyl)-dihydrolipoamide-E)

PDB for HMDB0006868 (S-(2-Methylpropionyl)-dihydrolipoamide-E)

3D PDB for HMDB0006868 (S-(2-Methylpropionyl)-dihydrolipoamide-E)

SMILES for HMDB0006868 (S-(2-Methylpropionyl)-dihydrolipoamide-E)

INCHI for HMDB0006868 (S-(2-Methylpropionyl)-dihydrolipoamide-E)

Structure for HMDB0006868 (S-(2-Methylpropionyl)-dihydrolipoamide-E)

3D Structure for HMDB0006868 (S-(2-Methylpropionyl)-dihydrolipoamide-E)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes