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Showing metabocard for (R)-Lipoic acid (HMDB0001451)

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enzymes (8) Show 8 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:43 UTC
HMDB IDHMDB0001451
Secondary Accession Numbers
  • HMDB01451
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.
Structure
Data?1676999743
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001451 ((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 HMDB0001451 ((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 HMDB0001451 ((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>
HMDB0001451

> <DATABASE_NAME>
hmdb

> <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 HMDB0001451 ((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 HMDB0001451 ((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 HMDB0001451 ((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 HMDB0001451 ((R)-Lipoic acid)

OC(=O)CCCC[C@@H]1CCSS1
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INCHI for HMDB0001451 ((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 JSmolView Stereo Labels
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
Chemical FormulaC8H14O2S2
Average Molecular Weight206.326
Monoisotopic Molecular Weight206.043521072
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
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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point60.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.29931661259
DarkChem[M+H]+146.29931661259
DarkChem[M-H]-140.3731661259
DarkChem[M-H]-140.3731661259
AllCCS[M+H]+143.44232859911
AllCCS[M-H]-149.64832859911
DeepCCS[M+H]+142.33430932474
DeepCCS[M-H]-139.93930932474
DeepCCS[M-2H]-175.29330932474
DeepCCS[M+Na]+149.6430932474
AllCCS[M+H]+143.432859911
AllCCS[M+H-H2O]+139.732859911
AllCCS[M+NH4]+147.032859911
AllCCS[M+Na]+148.032859911
AllCCS[M-H]-149.632859911
AllCCS[M+Na-2H]-150.932859911
AllCCS[M+HCOO]-152.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-Lipoic acidOC(=O)CCCC[C@@H]1CCSS13018.9Standard polar33892256
(R)-Lipoic acidOC(=O)CCCC[C@@H]1CCSS11761.0Standard non polar33892256
(R)-Lipoic acidOC(=O)CCCC[C@@H]1CCSS11862.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Lipoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCC[C@@H]1CCSS11966.8Semi standard non polar33892256
(R)-Lipoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1CCSS12207.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (R)-Lipoic acid GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-Lipoic acid GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-Lipoic acid GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-Lipoic acid GC-EI-TOF (Non-derivatized)splash10-0aba-3900000000-46fc1d57abcc26f6720e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Lipoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufu-5900000000-716655e029db4b97efd92016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Lipoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0hbi-6920000000-011fb15a0f9ca45130292017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Lipoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Lipoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4r-0940000000-dead1b29e79e0002da2a2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Lipoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0f8c-9200000000-b6035bdb4abd0d2672972012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Lipoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0059-9000000000-62e73cabbac1531f51452012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Lipoic acid 20V, Negative-QTOFsplash10-03di-9100000000-e420d2c931e889befcfa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Lipoic acid 10V, Negative-QTOFsplash10-0229-6900000000-90386d8704ab5bfe8e702021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Lipoic acid 40V, Negative-QTOFsplash10-03di-9000000000-042d27906c9bde31821f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Lipoic acid 35V, Negative-QTOFsplash10-03di-9000000000-6572cec5a1c9f68d96792021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 10V, Positive-QTOFsplash10-0a4r-0940000000-6cecd351951f396a30352016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 20V, Positive-QTOFsplash10-08gr-6910000000-f169816d57d2290b0d9e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 40V, Positive-QTOFsplash10-0m2c-9700000000-57ae386a681b98208a4b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 10V, Negative-QTOFsplash10-0a4i-1920000000-2b265e3ed116fbc0a2ea2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 20V, Negative-QTOFsplash10-0ab9-2910000000-9142e84d978f4a4815512016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 40V, Negative-QTOFsplash10-0a4i-9200000000-8bdfe1c35977a8c809852016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 10V, Positive-QTOFsplash10-0a4r-0970000000-0ae5b11a032d11c1ba6d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 20V, Positive-QTOFsplash10-03di-1900000000-decf255617c1bbd69bfb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 40V, Positive-QTOFsplash10-000i-6900000000-eb58a3d8135ba85d42832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 10V, Negative-QTOFsplash10-0a4i-0190000000-014d2ea36cfae0726a9e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 20V, Negative-QTOFsplash10-0a4i-5950000000-4e2dd5ccdcd5b0a936a02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Lipoic acid 40V, Negative-QTOFsplash10-0a59-9500000000-9bbbd7b252fb9a0b438d2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Neuron
  • Placenta
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.077 +/- 0.017 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00166
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDLIPOATE
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]

Enzymes

Enzyme Details
1. Pyruvate dehydrogenase protein X component, mitochondrial
General function:
Involved in acyltransferase activity
Specific function:
Required for anchoring dihydrolipoamide dehydrogenase (E3) to the dihydrolipoamide transacetylase (E2) core of the pyruvate dehydrogenase complexes of eukaryotes. This specific binding is essential for a functional PDH complex
Gene Name:
PDHX
Uniprot ID:
O00330
Molecular weight:
54121.8
Enzyme Details
2. Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial
General function:
Involved in acyltransferase activity
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
DLAT
Uniprot ID:
P10515
Molecular weight:
68996.03
Enzyme Details
3. NADPH--cytochrome P450 reductase
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name:
POR
Uniprot ID:
P16435
Molecular weight:
77047.575
Enzyme Details
4. 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
5. Glycine cleavage system H protein, mitochondrial
General function:
Involved in glycine catabolic process
Specific function:
The glycine cleavage system catalyzes the degradation of glycine. The H protein shuttles the methylamine group of glycine from the P protein to the T protein.
Gene Name:
GCSH
Uniprot ID:
P23434
Molecular weight:
Not Available
Enzyme Details
6. 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
7. 3-oxoacyl-[acyl-carrier-protein] synthase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
May play a role in the biosynthesis of lipoic acid as well as longer chain fatty acids required for optimal mitochondrial function.
Gene Name:
OXSM
Uniprot ID:
Q9NWU1
Molecular weight:
40034.535
Enzyme Details
8. Lipoyltransferase 1, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of the lipoyl group from lipoyl-AMP to the specific lysine residue of lipoyl domains of lipoate-dependent enzymes (By similarity).
Gene Name:
LIPT1
Uniprot ID:
Q9Y234
Molecular weight:
42478.8