Showing metabocard for Dihydrolipoate (MMDBc0047967)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:19:33 UTC
Update Date2022-09-01 02:13:43 UTC
Metabolite IDMMDBc0047967
Metabolite Identification
Common NameDihydrolipoate
DescriptionDihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups. It is optically active but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.( from Wiki). Inside the cell, alpha lipoic acid is readily reduced or broken down to dihydrolipoic acid. Dihydrolipoic acid is even more potent than alpha lipoic acid, neutralizing free radicals, preventing them from causing harm. It directly destroys damaging superoxide radicals, hydroperoxy radicals and hydroxyl radicals. It has been shown in vitro that dihydrolipoate (DL-6,8-dithioloctanoic acid) has antioxidant activity against microsomal lipid peroxidation.Dihydrolipoate is tested for its neuroprotective activity using models of hypoxic and excitotoxic neuronal damage in vitro and rodent models of cerebral ischemia in vivo. Dihydrolipoate, similarly to dimethylthiourea, is able to protect neurons against ischemic damage by diminishing the accumulation of reactive oxygen species within the cerebral tissue.(PMID: 1345759 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fe2d42f1430>


  Mrv0541 02241203502D          

 12 11  0  0  0  0            999 V2000
    7.0111   -8.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7283   -8.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3053   -8.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4453   -8.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8712   -8.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1540   -8.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5881   -8.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1571   -8.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8742   -8.3544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1519   -9.5874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4371   -8.7532    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5881   -7.5178    0.0000 S   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
  2  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fe2d42f1430>

HMDB0012210
     RDKit          3D
Dihydrolipoate
 28 27  0  0  0  0  0  0  0  0999 V2000
    3.2640    0.6797   -1.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8123    0.8155   -0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9785    1.5920   -0.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2732    0.1744    0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0220   -0.6148    0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627    0.1904    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3628   -0.7159    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5376    0.0657   -0.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9536    1.3816    0.7259 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7284   -0.8287   -0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9453   -0.1018   -1.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4368    1.2432   -0.0025 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7829    1.4607   -0.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0508   -0.5209    1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1419    0.9510    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2817   -1.4571    0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950   -1.0998    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0514    0.7221   -0.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393    0.9607    0.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427   -1.5413   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488   -1.1656    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3114    0.4901   -1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308    2.3563    0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9607   -1.3222    0.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5229   -1.6503   -1.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7874   -0.8237   -1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7400    0.3452   -2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7467    0.7603    1.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  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
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fe2d42f1430>


  Mrv0541 02241203502D          

 12 11  0  0  0  0            999 V2000
    7.0111   -8.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7283   -8.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3053   -8.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4453   -8.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8712   -8.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1540   -8.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5881   -8.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1571   -8.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8742   -8.3544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1519   -9.5874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4371   -8.7532    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5881   -7.5178    0.0000 S   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
  2  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  5  6  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047967

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CCCCC(S)CCS

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)

> <INCHI_KEY>
IZFHEQBZOYJLPK-UHFFFAOYSA-N

> <FORMULA>
C8H16O2S2

> <MOLECULAR_WEIGHT>
208.341

> <EXACT_MASS>
208.059171136

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.29676034092345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8-disulfanyloctanoic acid

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.2028031356666666

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.819261357853792

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.91049046621903

> <JCHEM_PKA_STRONGEST_BASIC>
-9.560948851014338

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
55.936600000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrolipoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007fe2d42f1430>

HMDB0012210
     RDKit          3D
Dihydrolipoate
 28 27  0  0  0  0  0  0  0  0999 V2000
    3.2640    0.6797   -1.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8123    0.8155   -0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9785    1.5920   -0.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2732    0.1744    0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0220   -0.6148    0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8627    0.1904    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3628   -0.7159    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5376    0.0657   -0.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9536    1.3816    0.7259 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7284   -0.8287   -0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9453   -0.1018   -1.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4368    1.2432   -0.0025 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7829    1.4607   -0.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0508   -0.5209    1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1419    0.9510    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2817   -1.4571    0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950   -1.0998    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0514    0.7221   -0.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5393    0.9607    0.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427   -1.5413   -0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488   -1.1656    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3114    0.4901   -1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308    2.3563    0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9607   -1.3222    0.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5229   -1.6503   -1.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7874   -0.8237   -1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7400    0.3452   -2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7467    0.7603    1.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  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
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
M  END
Download

PDB for #<Metabolite:0x00007fe2d42f1430>

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      13.087 -15.578   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.426 -16.339   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.770 -16.339   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.765 -15.578   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.093 -16.339   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.754 -15.578   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.431 -15.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.093 -16.356   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      18.432 -15.595   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      17.084 -17.896   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0       6.416 -16.339   0.000  0.00  0.00           S+0
HETATM   12  S   UNK     0      10.431 -14.033   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
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3D PDB for #<Metabolite:0x00007fe2d42f1430>

COMPND    HMDB0012210
HETATM    1  O1  UNL     1       3.264   0.680  -1.360  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.812   0.816  -0.245  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.979   1.592  -0.093  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.273   0.174   0.971  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.022  -0.615   0.757  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.863   0.190   0.241  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.363  -0.716   0.061  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.538   0.066  -0.454  1.00  0.00           C  
HETATM    9  S1  UNL     1      -1.954   1.382   0.726  1.00  0.00           S  
HETATM   10  C7  UNL     1      -2.728  -0.829  -0.599  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.945  -0.102  -1.115  1.00  0.00           C  
HETATM   12  S2  UNL     1      -4.437   1.243  -0.002  1.00  0.00           S  
HETATM   13  H1  UNL     1       5.783   1.461  -0.684  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.051  -0.521   1.381  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.142   0.951   1.778  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.282  -1.457   0.064  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.695  -1.100   1.700  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.051   0.722  -0.705  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.539   0.961   0.971  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.143  -1.541  -0.640  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.649  -1.166   1.032  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.311   0.490  -1.461  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.931   2.356   0.620  1.00  0.00           H  
HETATM   24  H12 UNL     1      -2.961  -1.322   0.356  1.00  0.00           H  
HETATM   25  H13 UNL     1      -2.523  -1.650  -1.342  1.00  0.00           H  
HETATM   26  H14 UNL     1      -4.787  -0.824  -1.130  1.00  0.00           H  
HETATM   27  H15 UNL     1      -3.740   0.345  -2.108  1.00  0.00           H  
HETATM   28  H16 UNL     1      -4.747   0.760   1.280  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9   10   22
CONECT    9   23
CONECT   10   11   24   25
CONECT   11   12   26   27
CONECT   12   28
END
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SMILES for #<Metabolite:0x00007fe2d42f1430>

OC(=O)CCCCC(S)CCS
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INCHI for #<Metabolite:0x00007fe2d42f1430>

InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
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Synonyms
ValueSource
6,8-Bis-sulfanyloctanoic acidChEBI
6,8-Dihydrothioctic acidChEBI
6,8-Dimercapto-octanoic acidChEBI
6,8-Dimercaptooctanoic acidChEBI
DHLAChEBI
Dihydro-alpha-lipoic acidChEBI
Dihydro-lipoic acidChEBI
Dihydrothioctic acidChEBI
Dihydrolipoic acidKegg
6,8-Bis-sulfanyloctanoateGenerator
6,8-Bis-sulphanyloctanoateGenerator
6,8-Bis-sulphanyloctanoic acidGenerator
6,8-DihydrothioctateGenerator
6,8-Dimercapto-octanoateGenerator
6,8-DimercaptooctanoateGenerator
Dihydro-a-lipoateGenerator
Dihydro-a-lipoic acidGenerator
Dihydro-alpha-lipoateGenerator
Dihydro-α-lipoateGenerator
Dihydro-α-lipoic acidGenerator
Dihydro-lipoateGenerator
DihydrothioctateGenerator
6,8-DisulfanyloctanoateHMDB
6,8-Disulfanyloctanoic acidHMDB
D,L-DihydrolipoateHMDB
D,L-Dihydrolipoic acidHMDB
dihydro-DL-alpha-LipoateHMDB
dihydro-DL-alpha-Lipoic acidHMDB
dihydro-Thioctic acidHMDB
dihydro-Thiocytic acidHMDB
DL-dihydro-a-6-Thioctic acidHMDB
DL-dihydro-alpha-6-Thioctic acidHMDB
Reduced DL-6,8-thioctic acidHMDB
Reduced lipoateHMDB
Reduced lipoic acidHMDB
Reduced thioctic acidHMDB
Dihydrolipoic acid, (+-)-isomerMeSH, HMDB
Dihydrolipoic acid, sodium saltMeSH, HMDB
Molecular FormulaC8H16O2S2
Average Mass208.341
Monoisotopic Mass208.059171136
IUPAC Name6,8-disulfanyloctanoic acid
Traditional Namedihydrolipoic acid
CAS Registry Number462-20-4
SMILES
OC(=O)CCCCC(S)CCS
InChI Identifier
InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
InChI KeyIZFHEQBZOYJLPK-UHFFFAOYSA-N