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Showing NP-Card for (R)-lipoic acid (NP0000443)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:47:04 UTC
NP-MRD IDNP0000443
Secondary Accession NumbersNone
Natural Product 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.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000443 ((R)-lipoic acid)


  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 NP0000443 ((R)-lipoic acid)

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 NP0000443 ((R)-lipoic acid)


  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>
NP0000443

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000443 ((R)-lipoic acid)

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

PDB for NP0000443 ((R)-lipoic acid)

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 NP0000443 ((R)-lipoic acid)

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 NP0000443 ((R)-lipoic acid)

OC(=O)CCCC[C@@H]1CCSS1
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INCHI for NP0000443 ((R)-lipoic acid)

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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View in JSmol
Synonyms
ValueSource
(+)-alpha-Lipoic acidChEBI
(R)-(+)-LipoateChEBI
(R)-(+)-Lipoic acidChEBI
(R)-1,2-Dithiolane-3-pentanoic acidChEBI
(R)-1,2-Dithiolane-3-valeric acidChEBI
(R)-6,8-Thioctic acidChEBI
alpha-Lipoic acidChEBI
Lipoic acidChEBI
R-(+)-Lipoic acidChEBI
R-LAChEBI
RLAChEBI
Thioctic acidChEBI
Thioctic acid D-formChEBI
1,2-Dithiolane-3R-pentanoic acidKegg
(+)-a-LipoateGenerator
(+)-a-Lipoic acidGenerator
(+)-alpha-LipoateGenerator
(+)-Α-lipoateGenerator
(+)-Α-lipoic acidGenerator
(R)-1,2-Dithiolane-3-pentanoateGenerator
(R)-1,2-Dithiolane-3-valerateGenerator
(R)-6,8-ThioctateGenerator
a-LipoateGenerator
a-Lipoic acidGenerator
alpha-LipoateGenerator
Α-lipoateGenerator
Α-lipoic acidGenerator
LipoateGenerator
R-(+)-LipoateGenerator
ThioctateGenerator
Thioctate D-formGenerator
1,2-Dithiolane-3R-pentanoateGenerator
(R)-LipoateGenerator
Acid, alpha-lipoicHMDB
alpha Lipoic acidHMDB
(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
(R)-Lipoic acidKEGG
Chemical FormulaC8H14O2S2
Average Mass206.3260 Da
Monoisotopic Mass206.04352 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Escherichia coliBacteria
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Porphyra tenera--
Solanum lycopersicumLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lipoic acids and derivatives. Lipoic acids and derivatives are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDithiolanes
Sub ClassLipoic acids and derivatives
Direct ParentLipoic acids and derivatives
Alternative Parents
Substituents
  • Lipoic_acid_derivative
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Thia fatty acid
  • Fatty acyl
  • Fatty acid
  • 1,2-dithiolane
  • Organic disulfide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point60.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP2.75ALOGPS
logP2.11ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity54.37 m³·mol⁻¹ChemAxon
Polarizability21.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001451
DrugBank IDDB00166
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022631
KNApSAcK IDC00000754
Chemspider ID5886
KEGG Compound IDC16241
BioCyc IDLIPOIC-ACID
BiGG ID35801
Wikipedia LinkLipoic_acid
METLIN ID126
PubChem Compound6112
PDB IDNot Available
ChEBI ID30314
Good Scents IDrw1582041
References
General References
  1. Teichert J, Tuemmers T, Achenbach H, Preiss C, Hermann R, Ruus P, Preiss R: Pharmacokinetics of alpha-lipoic acid in subjects with severe kidney damage and end-stage renal disease. J Clin Pharmacol. 2005 Mar;45(3):313-28. [PubMed:15703366 ]
  2. Arner ES, Nordberg J, Holmgren A: Efficient reduction of lipoamide and lipoic acid by mammalian thioredoxin reductase. Biochem Biophys Res Commun. 1996 Aug 5;225(1):268-74. [PubMed:8769129 ]
  3. Henriksen EJ, Saengsirisuwan V: Exercise training and antioxidants: relief from oxidative stress and insulin resistance. Exerc Sport Sci Rev. 2003 Apr;31(2):79-84. [PubMed:12715971 ]
  4. Loginov AS, Nilova TV, Bendikov EA, Petrakov AV: [Pharmacokinetics of preparations of lipoic acid and their effect on ATP synthesis, processes of microsomal and cytosol oxidation in hepatocytes in liver damage in man]. Farmakol Toksikol. 1989 Jul-Aug;52(4):78-82. [PubMed:2509239 ]
  5. Baker H, Deangelis B, Baker ER, Hutner SH: A practical assay of lipoate in biologic fluids and liver in health and disease. Free Radic Biol Med. 1998 Sep;25(4-5):473-9. [PubMed:9741583 ]
  6. Konrad D: Utilization of the insulin-signaling network in the metabolic actions of alpha-lipoic acid-reduction or oxidation? Antioxid Redox Signal. 2005 Jul-Aug;7(7-8):1032-9. [PubMed:15998258 ]
  7. Bruggraber SF, Leung PS, Amano K, Quan C, Kurth MJ, Nantz MH, Benson GD, Van de Water J, Luketic V, Roche TE, Ansari AA, Coppel RL, Gershwin ME: Autoreactivity to lipoate and a conjugated form of lipoate in primary biliary cirrhosis. Gastroenterology. 2003 Dec;125(6):1705-13. [PubMed:14724823 ]
  8. Redden PR, Melanson RL, Douglas JA, Dick AJ: Acyloxymethyl acidic drug derivatives: in vitro hydrolytic reactivity. Int J Pharm. 1999 Apr 15;180(2):151-60. [PubMed:10370185 ]
  9. Tankova T, Cherninkova S, Koev D: Treatment for diabetic mononeuropathy with alpha-lipoic acid. Int J Clin Pract. 2005 Jun;59(6):645-50. [PubMed:15924591 ]
  10. Chevion S, Hofmann M, Ziegler R, Chevion M, Nawroth PP: The antioxidant properties of thioctic acid: characterization by cyclic voltammetry. Biochem Mol Biol Int. 1997 Feb;41(2):317-27. [PubMed:9063572 ]
  11. Barbiroli B, Medori R, Tritschler HJ, Klopstock T, Seibel P, Reichmann H, Iotti S, Lodi R, Zaniol P: Lipoic (thioctic) acid increases brain energy availability and skeletal muscle performance as shown by in vivo 31P-MRS in a patient with mitochondrial cytopathy. J Neurol. 1995 Jul;242(7):472-7. [PubMed:7595680 ]
  12. Burke DG, Chilibeck PD, Parise G, Tarnopolsky MA, Candow DG: Effect of alpha-lipoic acid combined with creatine monohydrate on human skeletal muscle creatine and phosphagen concentration. Int J Sport Nutr Exerc Metab. 2003 Sep;13(3):294-302. [PubMed:14669930 ]
  13. Haj-Yehia AI, Assaf P, Nassar T, Katzhendler J: Determination of lipoic acid and dihydrolipoic acid in human plasma and urine by high-performance liquid chromatography with fluorimetric detection. J Chromatogr A. 2000 Feb 18;870(1-2):381-8. [PubMed:10722093 ]
  14. Nagamatsu M, Nickander KK, Schmelzer JD, Raya A, Wittrock DA, Tritschler H, Low PA: Lipoic acid improves nerve blood flow, reduces oxidative stress, and improves distal nerve conduction in experimental diabetic neuropathy. Diabetes Care. 1995 Aug;18(8):1160-7. [PubMed:7587852 ]
  15. Steinmann B, Gitzelmann R: Strychnine treatment attempted in newborn twins with severe nonketotic hyperglycinemia. Helv Paediatr Acta. 1979;34(6):589-99. [PubMed:541222 ]
  16. Lee WJ, Lee IK, Kim HS, Kim YM, Koh EH, Won JC, Han SM, Kim MS, Jo I, Oh GT, Park IS, Youn JH, Park SW, Lee KU, Park JY: Alpha-lipoic acid prevents endothelial dysfunction in obese rats via activation of AMP-activated protein kinase. Arterioscler Thromb Vasc Biol. 2005 Dec;25(12):2488-94. Epub 2005 Oct 13. [PubMed:16224049 ]
  17. McCormick DB: A trail of research on cofactors: an odyssey with friends. J Nutr. 2000 Feb;130(2S Suppl):323S-330S. [PubMed:10721897 ]
  18. Semenova TV, Azhitskii GIu, Sarnatskaia VV, Nikolaev VG: [Effect of various specific agents on the heat stability of human serum albumin]. Ukr Biokhim Zh (1978). 1993 Sep-Oct;65(5):26-30. [PubMed:8160293 ]