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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:22 UTC

HMDB ID

HMDB0000985

Secondary Accession Numbers

HMDB0006948
HMDB00985
HMDB06948

Metabolite Identification

Common Name

Dihydrolipoamide

Description

Dihydrolipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG ID C00579). It is converted to lipoamide via the enzyme dihydrolipoamide dehydrogenase [EC:1.8.1.4]. Dihydrolipoamide is also a substrate of enzyme Acyltransferases [EC 2.3.1.-]. (KEGG).

Structure

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

HMDB0000985
     RDKit          3D
Dihydrolipoamide
 29 28  0  0  0  0  0  0  0  0999 V2000
    4.1040    1.9360    0.5509 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8491    0.8947   -0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8573    0.0203   -0.5345 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    0.5899   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0955   -0.7513   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176   -1.2049   -0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2839   -0.2175    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121   -0.6303   -0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1117   -2.2397    0.4728 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6135    0.4606    0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0626    0.2113    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0077    1.5972    0.6984 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248    2.5777    0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6793   -0.1469    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    1.4075   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4878    0.5719   -1.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2497   -0.7138    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -1.4855   -0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400   -2.1670    0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6276   -1.4306   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1312    0.8119   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294   -0.2256    1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124   -0.6830   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154   -3.2550   -0.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3092    1.4010   -0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4377    0.5135    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3864   -0.7460    0.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624    0.1734   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1743    2.7306    0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
M  END

HMDB0000985
     RDKit          3D
Dihydrolipoamide
 29 28  0  0  0  0  0  0  0  0999 V2000
    4.1040    1.9360    0.5509 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8491    0.8947   -0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8573    0.0203   -0.5345 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    0.5899   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0955   -0.7513   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176   -1.2049   -0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2839   -0.2175    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121   -0.6303   -0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1117   -2.2397    0.4728 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6135    0.4606    0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0626    0.2113    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0077    1.5972    0.6984 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248    2.5777    0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6793   -0.1469    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    1.4075   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4878    0.5719   -1.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2497   -0.7138    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -1.4855   -0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400   -2.1670    0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6276   -1.4306   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1312    0.8119   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294   -0.2256    1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124   -0.6830   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154   -3.2550   -0.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3092    1.4010   -0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4377    0.5135    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3864   -0.7460    0.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624    0.1734   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1743    2.7306    0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  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      23.145 -16.596   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.375 -17.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.685 -16.596   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.835 -17.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.685 -13.929   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.145 -13.929   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.455 -15.262   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.065 -19.263   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      18.525 -19.263   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      20.835 -20.597   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0      22.375 -12.595   0.000  0.00  0.00           S+0
HETATM   12  S   UNK     0      26.995 -15.262   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    7    6                                                       
CONECT    6    5   11                                                       
CONECT    7    3    5   12                                                  
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0000985
HETATM    1  N1  UNL     1       4.104   1.936   0.551  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.849   0.895  -0.162  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.857   0.020  -0.535  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.467   0.590  -0.613  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.095  -0.751  -0.048  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.718  -1.205  -0.416  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.284  -0.217   0.093  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.712  -0.630  -0.254  1.00  0.00           C  
HETATM    9  S1  UNL     1      -2.112  -2.240   0.473  1.00  0.00           S  
HETATM   10  C7  UNL     1      -2.613   0.461   0.272  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.063   0.211   0.013  1.00  0.00           C  
HETATM   12  S2  UNL     1      -5.008   1.597   0.698  1.00  0.00           S  
HETATM   13  H1  UNL     1       3.325   2.578   0.817  1.00  0.00           H  
HETATM   14  H2  UNL     1       5.679  -0.147   0.027  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.816   1.407  -0.301  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.488   0.572  -1.739  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.250  -0.714   1.037  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.834  -1.485  -0.445  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.540  -2.167   0.129  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.628  -1.431  -1.480  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.131   0.812  -0.231  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.229  -0.226   1.203  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.812  -0.683  -1.352  1.00  0.00           H  
HETATM   24  H12 UNL     1      -2.115  -3.255  -0.504  1.00  0.00           H  
HETATM   25  H13 UNL     1      -2.309   1.401  -0.219  1.00  0.00           H  
HETATM   26  H14 UNL     1      -2.438   0.513   1.373  1.00  0.00           H  
HETATM   27  H15 UNL     1      -4.386  -0.746   0.492  1.00  0.00           H  
HETATM   28  H16 UNL     1      -4.262   0.173  -1.079  1.00  0.00           H  
HETATM   29  H17 UNL     1      -4.174   2.731   0.717  1.00  0.00           H  
CONECT    1    2    2   13
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   10   23
CONECT    9   24
CONECT   10   11   25   26
CONECT   11   12   27   28
CONECT   12   29
END

HMDB0000985
     RDKit          3D
Dihydrolipoamide
 29 28  0  0  0  0  0  0  0  0999 V2000
    4.1040    1.9360    0.5509 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8491    0.8947   -0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8573    0.0203   -0.5345 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    0.5899   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0955   -0.7513   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176   -1.2049   -0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2839   -0.2175    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121   -0.6303   -0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1117   -2.2397    0.4728 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6135    0.4606    0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0626    0.2113    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0077    1.5972    0.6984 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248    2.5777    0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6793   -0.1469    0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    1.4075   -0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4878    0.5719   -1.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2497   -0.7138    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -1.4855   -0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400   -2.1670    0.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6276   -1.4306   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1312    0.8119   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294   -0.2256    1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8124   -0.6830   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154   -3.2550   -0.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3092    1.4010   -0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4377    0.5135    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3864   -0.7460    0.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624    0.1734   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1743    2.7306    0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,8-Dimercaptooctanamide	ChEBI
Dihydrothioctamide	ChEBI
6,8-Bis-sulfanyloctanamide	HMDB
6,8-Dimercapto-octanamide	HMDB
6,8-Disulfanyloctanamide	HMDB
Dihydrolipoamide, (+-)-isomer	HMDB

Chemical Formula

C₈H₁₇NOS₂

Average Molecular Weight

207.357

Monoisotopic Molecular Weight

207.075155551

IUPAC Name

6,8-disulfanyloctanimidic acid

Traditional Name

dihydrothioctamide

CAS Registry Number

3884-47-7

SMILES

OC(=N)CCCCC(S)CCS

InChI Identifier

InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10)

InChI Key

VLYUGYAKYZETRF-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
Primary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Alkylthiol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:17694 )
dithiol (CHEBI:17694 )
a small molecule (DIHYDROLIPOAMIDE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0000985)

Cytoplasm (HMDB: HMDB0000985)
Cell membrane (HMDB: HMDB0000985)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000985)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000985)

Source

Endogenous

Endogenous (HMDB: HMDB0000985)

Plant

Animal

Animal (HMDB: HMDB0000985)

Exogenous

Food

Food (HMDB: HMDB0000985)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000985)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000985)
Pyruvate Metabolism (PathBank: SMP0087394)
Valine, Leucine, and Isoleucine Degradation (PathBank: SMP0063689)
Glycolysis and Pyruvate Dehydrogenase (PathBank: SMP0000807)

Disease pathway

2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120439)
Methylmalonate Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120523)
Isovaleric Acidemia (PathBank: SMP0120589)
3-Methylglutaconic Aciduria Type I (PathBank: SMP0120663)
Beta-Ketothiolase Deficiency (PathBank: SMP0120679)
Leigh Syndrome (PathBank: SMP0120726)
3-Hydroxyisobutyric Aciduria (PathBank: SMP0120806)
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I (PathBank: SMP0120441)
3-Methylglutaconic Aciduria Type IV (PathBank: SMP0120444)
Methylmalonic Aciduria (PathBank: SMP0120525)
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency) (PathBank: SMP0120533)
Pyruvate Kinase Deficiency (PathBank: SMP0120623)
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency (PathBank: SMP0120661)
3-Methylglutaconic Aciduria Type III (PathBank: SMP0120664)
Primary Hyperoxaluria II, PH2 (PathBank: SMP0120841)
Maple Syrup Urine Disease (PathBank: SMP0120516)
Pyruvate Dehydrogenase Complex Deficiency (PathBank: SMP0120531)
Propionic Acidemia (PathBank: SMP0120537)
Isobutyryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120588)
Isovaleric Aciduria (PathBank: SMP0120723)
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency (PathBank: SMP0120586)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0000137)

Lipid metabolism pathway (HMDB: HMDB0000985)

Biochemical process

Lipid transport (HMDB: HMDB0000985)

Role

Biological role

Energy source (HMDB: HMDB0000985)

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	0.099 g/L	ALOGPS
logP	2.22	ALOGPS
logP	1.44	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.68	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	44.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.7 m³·mol⁻¹	ChemAxon
Polarizability	23.77 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]+	146.928	31661259
DarkChem	[M-H]-	142.641	31661259
AllCCS	[M+H]+	145.297	32859911
AllCCS	[M-H]-	150.976	32859911
DeepCCS	[M+H]+	148.347	30932474
DeepCCS	[M-H]-	145.931	30932474
DeepCCS	[M-2H]-	181.504	30932474
DeepCCS	[M+Na]+	156.714	30932474
AllCCS	[M+H]+	145.3	32859911
AllCCS	[M+H-H2O]+	141.8	32859911
AllCCS	[M+NH4]+	148.5	32859911
AllCCS	[M+Na]+	149.5	32859911
AllCCS	[M-H]-	151.0	32859911
AllCCS	[M+Na-2H]-	152.9	32859911
AllCCS	[M+HCOO]-	155.1	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.	3.73 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9669 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.66 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2509.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	340.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	135.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	201.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	240.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	444.5 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	563.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	319.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	995.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	352.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1164.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	300.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	306.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	430.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	458.8 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	129.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrolipoamide	OC(=N)CCCCC(S)CCS	3229.4	Standard polar	33892256
Dihydrolipoamide	OC(=N)CCCCC(S)CCS	1863.1	Standard non polar	33892256
Dihydrolipoamide	OC(=N)CCCCC(S)CCS	1961.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrolipoamide,1TMS,isomer #1	C[Si](C)(C)OC(=N)CCCCC(S)CCS	2065.0	Semi standard non polar	33892256
Dihydrolipoamide,1TMS,isomer #2	C[Si](C)(C)SC(CCS)CCCCC(=N)O	2131.6	Semi standard non polar	33892256
Dihydrolipoamide,1TMS,isomer #3	C[Si](C)(C)SCCC(S)CCCCC(=N)O	2174.0	Semi standard non polar	33892256
Dihydrolipoamide,1TMS,isomer #4	C[Si](C)(C)N=C(O)CCCCC(S)CCS	2047.1	Semi standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #1	C[Si](C)(C)OC(=N)CCCCC(CCS)S[Si](C)(C)C	2177.3	Semi standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #1	C[Si](C)(C)OC(=N)CCCCC(CCS)S[Si](C)(C)C	2113.2	Standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #1	C[Si](C)(C)OC(=N)CCCCC(CCS)S[Si](C)(C)C	2586.3	Standard polar	33892256
Dihydrolipoamide,2TMS,isomer #2	C[Si](C)(C)OC(=N)CCCCC(S)CCS[Si](C)(C)C	2230.3	Semi standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #2	C[Si](C)(C)OC(=N)CCCCC(S)CCS[Si](C)(C)C	2123.6	Standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #2	C[Si](C)(C)OC(=N)CCCCC(S)CCS[Si](C)(C)C	2676.7	Standard polar	33892256
Dihydrolipoamide,2TMS,isomer #3	C[Si](C)(C)N=C(CCCCC(S)CCS)O[Si](C)(C)C	2062.2	Semi standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #3	C[Si](C)(C)N=C(CCCCC(S)CCS)O[Si](C)(C)C	1996.1	Standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #3	C[Si](C)(C)N=C(CCCCC(S)CCS)O[Si](C)(C)C	2497.1	Standard polar	33892256
Dihydrolipoamide,2TMS,isomer #4	C[Si](C)(C)SCCC(CCCCC(=N)O)S[Si](C)(C)C	2258.7	Semi standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #4	C[Si](C)(C)SCCC(CCCCC(=N)O)S[Si](C)(C)C	2168.5	Standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #4	C[Si](C)(C)SCCC(CCCCC(=N)O)S[Si](C)(C)C	2815.7	Standard polar	33892256
Dihydrolipoamide,2TMS,isomer #5	C[Si](C)(C)N=C(O)CCCCC(CCS)S[Si](C)(C)C	2122.2	Semi standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #5	C[Si](C)(C)N=C(O)CCCCC(CCS)S[Si](C)(C)C	2067.0	Standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #5	C[Si](C)(C)N=C(O)CCCCC(CCS)S[Si](C)(C)C	2578.5	Standard polar	33892256
Dihydrolipoamide,2TMS,isomer #6	C[Si](C)(C)N=C(O)CCCCC(S)CCS[Si](C)(C)C	2179.7	Semi standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #6	C[Si](C)(C)N=C(O)CCCCC(S)CCS[Si](C)(C)C	2084.0	Standard non polar	33892256
Dihydrolipoamide,2TMS,isomer #6	C[Si](C)(C)N=C(O)CCCCC(S)CCS[Si](C)(C)C	2668.2	Standard polar	33892256
Dihydrolipoamide,3TMS,isomer #1	C[Si](C)(C)OC(=N)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C	2300.1	Semi standard non polar	33892256
Dihydrolipoamide,3TMS,isomer #1	C[Si](C)(C)OC(=N)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C	2304.3	Standard non polar	33892256
Dihydrolipoamide,3TMS,isomer #1	C[Si](C)(C)OC(=N)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C	2556.8	Standard polar	33892256
Dihydrolipoamide,3TMS,isomer #2	C[Si](C)(C)N=C(CCCCC(CCS)S[Si](C)(C)C)O[Si](C)(C)C	2142.2	Semi standard non polar	33892256
Dihydrolipoamide,3TMS,isomer #2	C[Si](C)(C)N=C(CCCCC(CCS)S[Si](C)(C)C)O[Si](C)(C)C	2188.2	Standard non polar	33892256
Dihydrolipoamide,3TMS,isomer #2	C[Si](C)(C)N=C(CCCCC(CCS)S[Si](C)(C)C)O[Si](C)(C)C	2399.1	Standard polar	33892256
Dihydrolipoamide,3TMS,isomer #3	C[Si](C)(C)N=C(CCCCC(S)CCS[Si](C)(C)C)O[Si](C)(C)C	2189.1	Semi standard non polar	33892256
Dihydrolipoamide,3TMS,isomer #3	C[Si](C)(C)N=C(CCCCC(S)CCS[Si](C)(C)C)O[Si](C)(C)C	2175.1	Standard non polar	33892256
Dihydrolipoamide,3TMS,isomer #3	C[Si](C)(C)N=C(CCCCC(S)CCS[Si](C)(C)C)O[Si](C)(C)C	2499.8	Standard polar	33892256
Dihydrolipoamide,3TMS,isomer #4	C[Si](C)(C)N=C(O)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C	2259.4	Semi standard non polar	33892256
Dihydrolipoamide,3TMS,isomer #4	C[Si](C)(C)N=C(O)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C	2267.0	Standard non polar	33892256
Dihydrolipoamide,3TMS,isomer #4	C[Si](C)(C)N=C(O)CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C	2657.9	Standard polar	33892256
Dihydrolipoamide,4TMS,isomer #1	C[Si](C)(C)N=C(CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C)O[Si](C)(C)C	2286.9	Semi standard non polar	33892256
Dihydrolipoamide,4TMS,isomer #1	C[Si](C)(C)N=C(CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C)O[Si](C)(C)C	2334.0	Standard non polar	33892256
Dihydrolipoamide,4TMS,isomer #1	C[Si](C)(C)N=C(CCCCC(CCS[Si](C)(C)C)S[Si](C)(C)C)O[Si](C)(C)C	2297.1	Standard polar	33892256
Dihydrolipoamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=N)CCCCC(S)CCS	2309.4	Semi standard non polar	33892256
Dihydrolipoamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)SC(CCS)CCCCC(=N)O	2343.2	Semi standard non polar	33892256
Dihydrolipoamide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCCC(S)CCCCC(=N)O	2396.0	Semi standard non polar	33892256
Dihydrolipoamide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=C(O)CCCCC(S)CCS	2264.5	Semi standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=N)CCCCC(CCS)S[Si](C)(C)C(C)(C)C	2662.6	Semi standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=N)CCCCC(CCS)S[Si](C)(C)C(C)(C)C	2532.3	Standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=N)CCCCC(CCS)S[Si](C)(C)C(C)(C)C	2712.0	Standard polar	33892256
Dihydrolipoamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=N)CCCCC(S)CCS[Si](C)(C)C(C)(C)C	2720.4	Semi standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=N)CCCCC(S)CCS[Si](C)(C)C(C)(C)C	2542.8	Standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=N)CCCCC(S)CCS[Si](C)(C)C(C)(C)C	2810.6	Standard polar	33892256
Dihydrolipoamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(CCCCC(S)CCS)O[Si](C)(C)C(C)(C)C	2508.3	Semi standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(CCCCC(S)CCS)O[Si](C)(C)C(C)(C)C	2379.4	Standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(CCCCC(S)CCS)O[Si](C)(C)C(C)(C)C	2687.1	Standard polar	33892256
Dihydrolipoamide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)SCCC(CCCCC(=N)O)S[Si](C)(C)C(C)(C)C	2749.4	Semi standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)SCCC(CCCCC(=N)O)S[Si](C)(C)C(C)(C)C	2621.8	Standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)SCCC(CCCCC(=N)O)S[Si](C)(C)C(C)(C)C	2836.7	Standard polar	33892256
Dihydrolipoamide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N=C(O)CCCCC(CCS)S[Si](C)(C)C(C)(C)C	2619.6	Semi standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N=C(O)CCCCC(CCS)S[Si](C)(C)C(C)(C)C	2479.4	Standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N=C(O)CCCCC(CCS)S[Si](C)(C)C(C)(C)C	2734.8	Standard polar	33892256
Dihydrolipoamide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N=C(O)CCCCC(S)CCS[Si](C)(C)C(C)(C)C	2662.3	Semi standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N=C(O)CCCCC(S)CCS[Si](C)(C)C(C)(C)C	2502.8	Standard non polar	33892256
Dihydrolipoamide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N=C(O)CCCCC(S)CCS[Si](C)(C)C(C)(C)C	2824.3	Standard polar	33892256
Dihydrolipoamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=N)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	3036.8	Semi standard non polar	33892256
Dihydrolipoamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=N)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2909.2	Standard non polar	33892256
Dihydrolipoamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=N)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2767.0	Standard polar	33892256
Dihydrolipoamide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(CCCCC(CCS)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2858.6	Semi standard non polar	33892256
Dihydrolipoamide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(CCCCC(CCS)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2740.4	Standard non polar	33892256
Dihydrolipoamide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C(CCCCC(CCS)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2664.6	Standard polar	33892256
Dihydrolipoamide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(CCCCC(S)CCS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2905.5	Semi standard non polar	33892256
Dihydrolipoamide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(CCCCC(S)CCS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2741.5	Standard non polar	33892256
Dihydrolipoamide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C(CCCCC(S)CCS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2761.3	Standard polar	33892256
Dihydrolipoamide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=C(O)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2977.2	Semi standard non polar	33892256
Dihydrolipoamide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=C(O)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2858.0	Standard non polar	33892256
Dihydrolipoamide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N=C(O)CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C	2840.7	Standard polar	33892256
Dihydrolipoamide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3226.2	Semi standard non polar	33892256
Dihydrolipoamide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2986.5	Standard non polar	33892256
Dihydrolipoamide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CCCCC(CCS[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2688.1	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Mitochondria

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

FDB022352

KNApSAcK ID

Not Available

Chemspider ID

643

KEGG Compound ID

C00579

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17694

Food Biomarker Ontology

Not Available

VMH ID

DHLAM

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Weitzman, P. D. J.; Hewson, Janet K.; Parker, M. G. Preparation of dihydrolipoamide by electrolytic reduction. FEBS Letters (1974), 43(1), 101-3.

Material Safety Data Sheet (MSDS)

Not Available

General References

Brautigam CA, Chuang JL, Tomchick DR, Machius M, Chuang DT: Crystal structure of human dihydrolipoamide dehydrogenase: NAD+/NADH binding and the structural basis of disease-causing mutations. J Mol Biol. 2005 Jul 15;350(3):543-52. [PubMed:15946682 ]
Kim H: Asparagine-473 residue is important to the efficient function of human dihydrolipoamide dehydrogenase. J Biochem Mol Biol. 2005 Mar 31;38(2):248-52. [PubMed:15826505 ]
McMillan PJ, Stimmler LM, Foth BJ, McFadden GI, Muller S: The human malaria parasite Plasmodium falciparum possesses two distinct dihydrolipoamide dehydrogenases. Mol Microbiol. 2005 Jan;55(1):27-38. [PubMed:15612914 ]
Li XJ, Grunwald D, Mathieu J, Morel F, Stasia MJ: Crucial role of two potential cytosolic regions of Nox2, 191TSSTKTIRRS200 and 484DESQANHFAVHHDEEKD500, on NADPH oxidase activation. J Biol Chem. 2005 Apr 15;280(15):14962-73. Epub 2005 Jan 31. [PubMed:15684431 ]
Deres P, Halmosi R, Toth A, Kovacs K, Palfi A, Habon T, Czopf L, Kalai T, Hideg K, Sumegi B, Toth K: Prevention of doxorubicin-induced acute cardiotoxicity by an experimental antioxidant compound. J Cardiovasc Pharmacol. 2005 Jan;45(1):36-43. [PubMed:15613977 ]

Enzymes

Enzyme Details

1. Dihydrolipoyl dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes. Involved in the hyperactivation of spermatazoa during capacitation and in the spermatazoal acrosome reaction.
Gene Name:: DLD
Uniprot ID:: P09622
Molecular weight:: 54176.91

Reactions

Dihydrolipoamide + NAD → Lipoamide + NADH + Hydrogen Ion	details

Enzyme Details

2. Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial

General function:: Involved in acyltransferase activity
Specific function:: The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of 3 enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:: DLST
Uniprot ID:: P36957
Molecular weight:: 48754.87

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

Enzyme Details

4. Dihydrolipoamide S-acetyltransferase

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: DLAT
Uniprot ID:: Q86YI5
Molecular weight:: 68996.0

Showing metabocard for Dihydrolipoamide (HMDB0000985)

MOL for HMDB0000985 (Dihydrolipoamide)

3D MOL for HMDB0000985 (Dihydrolipoamide)

3D SDF for HMDB0000985 (Dihydrolipoamide)

3D-SDF for HMDB0000985 (Dihydrolipoamide)

PDB for HMDB0000985 (Dihydrolipoamide)

3D PDB for HMDB0000985 (Dihydrolipoamide)

SMILES for HMDB0000985 (Dihydrolipoamide)

INCHI for HMDB0000985 (Dihydrolipoamide)

Structure for HMDB0000985 (Dihydrolipoamide)

3D Structure for HMDB0000985 (Dihydrolipoamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions