Showing metabocard for (R)-Lipoic acid (MMDBc0000197)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:39:25 UTC
Update Date2024-04-30 19:31:27 UTC
Metabolite IDMMDBc0000197
Metabolite Identification
Common Name(R)-Lipoic acid
DescriptionLipoic acid is a vitamin-like antioxidant that acts as a free-radical scavenger. Alpha-lipoic acid is also known as thioctic acid. It is a naturally occurring compound that is synthesized by both plants and animals. Lipoic acid contains two thiol groups which may be either oxidized or reduced. The reduced form is known as dihydrolipoic acid (DHLA). Lipoic acid (Delta E= -0.288) is therefore capable of thiol-disulfide exchange, giving it antioxidant activity. Lipoate is a critical cofactor for aerobic metabolism, participating in the transfer of acyl or methylamine groups via the 2-Oxoacid dehydrogenase (2-OADH) or alpha-ketoglutarate dehydrogenase complex. This enzyme catalyzes the conversion of alpha-ketoglutarate to succinyl CoA. This activity results in the catabolism of the branched chain amino acids (leucine, isoleucine and valine). Lipoic acid also participates in the glycine cleavage system(GCV). The glycine cleavage system is a multi-enzyme complex that catalyzes the oxidation of glycine to form 5,10 methylene tetrahydrofolate, an important cofactor in nucleic acid synthesis. Since Lipoic acid is an essential cofactor for many enzyme complexes, it is essential for aerobic life as we know it. This system is used by many organisms and plays a crucial role in the photosynthetic carbon cycle. Lipoic acid was first postulated to be an effective antioxidant when it was found it prevented vitamin C and vitamin E deficiency. It is able to scavenge reactive oxygen species and reduce other metabolites, such as glutathione or vitamins, maintaining a healthy cellular redox state. Lipoic acid has been shown in cell culture experiments to increase cellular uptake of glucose by recruiting the glucose transporter GLUT4 to the cell membrane, suggesting its use in diabetes. Studies of rat aging have suggested that the use of L-carnitine and lipoic acid results in improved memory performance and delayed structural mitochondrial decay. As a result, it may be helpful for people with Alzheimer's disease or Parkinson's disease. -- Wikipedia .
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fd0f8117f30>


  Mrv1652305261923502D          

 12 12  0  0  0  0            999 V2000
   -0.0308    0.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -0.5669    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    0.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4433   -0.5669    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    0.2177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3511    0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0656    0.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801    0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945    0.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2090    0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2090    1.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9235    0.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fd0f8117f30>

HMDB0001451
     RDKit          3D
(R)-Lipoic acid
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.4270   -0.3763   -1.0240 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522   -0.5691    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4148   -1.2350    0.8430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2335   -0.1546    1.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383    0.4575    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748   -0.5409   -0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328    0.0606   -1.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268    0.5141   -0.7002 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2945   -0.5100    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1669    0.2725    1.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4493    0.9129   -0.0203 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0697    1.1240   -1.6813 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410   -1.0602    0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5472    0.5136    1.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774   -1.0876    1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4708    1.3925   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3369    0.8126    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1907   -1.3998   -0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2945   -0.9652   -1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8418   -0.5715   -2.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0840    0.9828   -2.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3209    1.3671   -0.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585   -1.2312    0.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0241   -1.0940   -0.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5354    1.0924    1.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5944   -0.3788    1.8941 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  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  1
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fd0f8117f30>


  Mrv1652305261923502D          

 12 12  0  0  0  0            999 V2000
   -0.0308    0.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -0.5669    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6982    0.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4433   -0.5669    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    0.2177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3511    0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0656    0.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801    0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945    0.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2090    0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2090    1.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9235    0.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000197

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CCCC[C@@H]1CCSS1

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1

> <INCHI_KEY>
AGBQKNBQESQNJD-SSDOTTSWSA-N

> <FORMULA>
C8H14O2S2

> <MOLECULAR_WEIGHT>
206.326

> <EXACT_MASS>
206.043521072

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.744975428939433

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
2.1137794076666667

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.523468122735193

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
54.3714

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lipoic acid

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007fd0f8117f30>

HMDB0001451
     RDKit          3D
(R)-Lipoic acid
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.4270   -0.3763   -1.0240 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522   -0.5691    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4148   -1.2350    0.8430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2335   -0.1546    1.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383    0.4575    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748   -0.5409   -0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328    0.0606   -1.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268    0.5141   -0.7002 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2945   -0.5100    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1669    0.2725    1.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4493    0.9129   -0.0203 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0697    1.1240   -1.6813 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410   -1.0602    0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5472    0.5136    1.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774   -1.0876    1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4708    1.3925   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3369    0.8126    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1907   -1.3998   -0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2945   -0.9652   -1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8418   -0.5715   -2.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0840    0.9828   -2.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3209    1.3671   -0.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585   -1.2312    0.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0241   -1.0940   -0.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5354    1.0924    1.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5944   -0.3788    1.8941 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  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  1
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
M  END
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PDB for #<Metabolite:0x00007fd0f8117f30>

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.057   1.312   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       0.713  -1.058   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      -1.303   0.406   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      -0.827  -1.058   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       1.188   0.406   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.522   1.176   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.856   0.406   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.190   1.176   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.523   0.406   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.857   1.176   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.857   2.716   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.191   0.406   0.000  0.00  0.00           O+0
CONECT    1    5    3                                                       
CONECT    2    5    4                                                       
CONECT    3    1    4                                                       
CONECT    4    2    3                                                       
CONECT    5    1    2    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for #<Metabolite:0x00007fd0f8117f30>

COMPND    HMDB0001451
HETATM    1  O1  UNL     1       3.427  -0.376  -1.024  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.352  -0.569   0.201  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.415  -1.235   0.843  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.233  -0.155   1.045  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.138   0.457   0.238  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.575  -0.541  -0.743  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.533   0.061  -1.569  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.627   0.514  -0.700  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.295  -0.510   0.148  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.167   0.272   1.141  1.00  0.00           C  
HETATM   11  S1  UNL     1      -4.449   0.913  -0.020  1.00  0.00           S  
HETATM   12  S2  UNL     1      -3.070   1.124  -1.681  1.00  0.00           S  
HETATM   13  H1  UNL     1       5.341  -1.060   0.478  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.547   0.514   1.882  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.877  -1.088   1.576  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.471   1.392  -0.286  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.337   0.813   0.951  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.191  -1.400  -0.128  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.295  -0.965  -1.440  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.842  -0.572  -2.402  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.084   0.983  -2.044  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.321   1.367  -0.064  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.659  -1.231   0.651  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.024  -1.094  -0.465  1.00  0.00           H  
HETATM   25  H13 UNL     1      -2.535   1.092   1.519  1.00  0.00           H  
HETATM   26  H14 UNL     1      -3.594  -0.379   1.894  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   12   22
CONECT    9   10   23   24
CONECT   10   11   25   26
CONECT   11   12
END
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SMILES for #<Metabolite:0x00007fd0f8117f30>

OC(=O)CCCC[C@@H]1CCSS1
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INCHI for #<Metabolite:0x00007fd0f8117f30>

InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
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Synonyms
ValueSource
(+)-alpha-Lipoic acidChEBI, HMDB
(R)-(+)-LipoateChEBI, KEGG
(R)-(+)-Lipoic acidChEBI, Generator
(R)-1,2-Dithiolane-3-pentanoic acidChEBI, HMDB
(R)-1,2-Dithiolane-3-valeric acidChEBI, HMDB
(R)-6,8-Thioctic acidChEBI, HMDB
alpha-Lipoic acidChEBI, HMDB
Lipoic acidChEBI, HMDB
R-(+)-Lipoic acidChEBI, KEGG
R-LAChEBI, HMDB
RLAChEBI, HMDB
Thioctic acidChEBI, HMDB
Thioctic acid D-formChEBI, HMDB
(+)-a-LipoateGenerator, HMDB
(+)-a-Lipoic acidGenerator, HMDB
(+)-alpha-LipoateGenerator, HMDB
(+)-α-lipoateGenerator, HMDB
(+)-α-lipoic acidGenerator, HMDB
(R)-LipoateGenerator
(R)-1,2-Dithiolane-3-pentanoateGenerator, HMDB
(R)-1,2-Dithiolane-3-valerateGenerator, HMDB
(R)-6,8-ThioctateGenerator, HMDB
a-LipoateGenerator, HMDB
a-Lipoic acidGenerator, HMDB
alpha-LipoateGenerator, HMDB
α-lipoateGenerator, HMDB
α-Lipoic acidGenerator, HMDB
LipoateGenerator, HMDB
R-(+)-LipoateGenerator
ThioctateGenerator, HMDB
Thioctate D-formGenerator, HMDB
Acid, alpha-lipoicMeSH, HMDB
alpha Lipoic acidMeSH, HMDB
1,2-Dithiolane-3R-pentanoic acidKEGG
1,2-Dithiolane-3R-pentanoateGenerator
(R)-Lipoic acidKEGG
(3R)-1,2-Dithiolane-3-pentanoic acidHMDB
(R)-(+)-1,2-Dithiolane-3-pentanoic acidHMDB
(R)-(+)-alpha-Lipoic acidHMDB
(R)-(+)-α-Lipoic acidHMDB
(R)-5-(1,2-Dithiolan-3-yl)pentanoicacidHMDB
(R)-alpha-Lipoic acidHMDB
(R)-α-Lipoic acidHMDB
ALAHMDB
alpha-(+)-Lipoic acidHMDB
α-(+)-Lipoic acidHMDB
1,2-Dithiolane-3-valeric acidHMDB
5-(1,2-Dithiolan-3-yl)pentanoic acidHMDB
5-(1,2-Dithiolan-3-yl)valeric acidHMDB
6,8-Thioctic acidHMDB
6-Thioctic acidHMDB
Molecular FormulaC8H14O2S2
Average Mass206.326
Monoisotopic Mass206.043521072
IUPAC Name5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
Traditional Namelipoic acid
CAS Registry Number1200-22-2
SMILES
OC(=O)CCCC[C@@H]1CCSS1
InChI Identifier
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
InChI KeyAGBQKNBQESQNJD-SSDOTTSWSA-N