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Showing NP-Card for alpha-Lipoic acid (NP0002784)

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Record Information
Version2.0
Created at2020-11-23 19:40:21 UTC
Updated at2025-02-11 15:48:58 UTC
NP-MRD IDNP0002784
Natural Product DOIhttps://doi.org/10.57994/2994
Secondary Accession NumbersNone
Natural Product Identification
Common Namealpha-Lipoic acid
Provided ByBMRBBMRB logo
Description(S)-Lipoic acid, also known as L-6-thioctic acid or (S)-a-lipoate, 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 (S)-Lipoic acid exists in all living organisms, ranging from bacteria to humans. alpha-Lipoic acid was first documented in 1951 (PMID: 14854913). Based on a literature review a small amount of articles have been published on (S)-Lipoic acid (PMID: 10966480) (PMID: 8573188) (PMID: 7669066).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002784 (alpha-Lipoic acid)


     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
   -5.8149   -1.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0522   -0.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7894    1.2164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5522   -0.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0523   -0.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524   -0.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9475   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4475   -0.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9116   -0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6742    0.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6815    1.9266    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053    1.3299    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2893    1.2311    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5376    1.3953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5669   -1.6045    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0670   -1.6192    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0376    1.3807    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5671   -1.6339    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377    1.3660    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9622    1.3513    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329   -1.6486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761   -1.6535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2758   -1.1130    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4341   -1.9115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6888    1.9069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8791   -0.0914    0.0000 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  6
  4 15  1  0
  5 16  1  6
  5 17  1  0
  6 18  1  6
  6 19  1  0
  7 20  1  6
  7 21  1  0
  8 22  1  1
  9 23  1  6
  9 24  1  0
 10 25  1  6
 10 26  1  0
M  END
Download

3D MOL for NP0002784 (alpha-Lipoic acid)

NP0002784
     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
    3.7277    0.6792    1.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6061   -0.0203    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2979   -1.2353    0.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    0.4395   -0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3369    0.6999   -0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8713   -0.5999    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395   -0.6013    0.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5606   -0.1202    0.0129 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8700   -0.2260    0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9465    0.5992    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3736    1.9946   -0.7487 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2925    1.6631   -0.2865 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0880   -1.9758   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7207   -0.3551   -1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870    1.3950   -1.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7291    0.9899   -1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468    1.4883    0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871   -1.3187   -0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715   -1.0457    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6899   -1.6283    1.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323    0.0556    1.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5387   -0.6230   -0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786   -0.0469    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628   -1.3149    0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6929    0.0556   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5540    1.0515    1.0836 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  6
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
M  END
Download

3D SDF for NP0002784 (alpha-Lipoic acid)


     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
   -5.8149   -1.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0522   -0.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7894    1.2164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5522   -0.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0523   -0.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524   -0.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9475   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4475   -0.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9116   -0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6742    0.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6815    1.9266    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053    1.3299    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2893    1.2311    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5376    1.3953    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5669   -1.6045    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0670   -1.6192    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0376    1.3807    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5671   -1.6339    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377    1.3660    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9622    1.3513    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329   -1.6486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2761   -1.6535    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2758   -1.1130    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4341   -1.9115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6888    1.9069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8791   -0.0914    0.0000 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  6
  4 15  1  0
  5 16  1  6
  5 17  1  0
  6 18  1  6
  6 19  1  0
  7 20  1  6
  7 21  1  0
  8 22  1  1
  9 23  1  6
  9 24  1  0
 10 25  1  6
 10 26  1  0
M  END
> <DATABASE_ID>
NP0002784

> <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-/m0/s1

> <INCHI_KEY>
AGBQKNBQESQNJD-ZETCQYMHSA-N

> <FORMULA>
C8H14O2S2

> <MOLECULAR_WEIGHT>
206.326

> <EXACT_MASS>
206.043521072

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.913641567992176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(3S)-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>
54.37140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S-LA

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002784 (alpha-Lipoic acid)

NP0002784
     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
    3.7277    0.6792    1.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6061   -0.0203    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2979   -1.2353    0.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    0.4395   -0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3369    0.6999   -0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8713   -0.5999    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395   -0.6013    0.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5606   -0.1202    0.0129 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8700   -0.2260    0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9465    0.5992    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3736    1.9946   -0.7487 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2925    1.6631   -0.2865 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0880   -1.9758   -0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7207   -0.3551   -1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870    1.3950   -1.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7291    0.9899   -1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468    1.4883    0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871   -1.3187   -0.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715   -1.0457    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6899   -1.6283    1.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323    0.0556    1.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5387   -0.6230   -0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786   -0.0469    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628   -1.3149    0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6929    0.0556   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5540    1.0515    1.0836 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  6
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
M  END
Download

PDB for NP0002784 (alpha-Lipoic acid)

HEADER    PROTEIN                                 21-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-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
Download

3D PDB for NP0002784 (alpha-Lipoic acid)

COMPND    NP0002784
HETATM    1  O1  UNL     1       3.728   0.679   1.264  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.606  -0.020   0.211  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.298  -1.235   0.165  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.762   0.439  -0.913  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.337   0.700  -0.332  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.871  -0.600   0.201  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.440  -0.601   0.878  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.561  -0.120   0.013  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.870  -0.226   0.708  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.947   0.599   0.238  1.00  0.00           C  
HETATM   11  S1  UNL     1      -3.374   1.995  -0.749  1.00  0.00           S  
HETATM   12  S2  UNL     1      -1.293   1.663  -0.287  1.00  0.00           S  
HETATM   13  H1  UNL     1       4.088  -1.976  -0.482  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.721  -0.355  -1.659  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.187   1.395  -1.294  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.729   0.990  -1.233  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.347   1.488   0.401  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.887  -1.319  -0.685  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.671  -1.046   0.887  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.690  -1.628   1.290  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.432   0.056   1.801  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.539  -0.623  -0.948  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.679  -0.047   1.790  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.163  -1.315   0.675  1.00  0.00           H  
HETATM   25  H13 UNL     1      -4.693   0.056  -0.382  1.00  0.00           H  
HETATM   26  H14 UNL     1      -4.554   1.051   1.084  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 NP0002784 (alpha-Lipoic acid)

OC(=O)CCCC[C@H]1CCSS1
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INCHI for NP0002784 (alpha-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-/m0/s1
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Synonyms
ValueSource
(S)-(-)-Lipoic acidChEBI
(S)-1,2-Dithiolane-3-pentanoic acidChEBI
(S)-alpha-Lipoic acidChEBI
L-1,2-Dithiolane 3-valeric acidChEBI
L-6,8-Thioctic acidChEBI
L-6-Thioctic acidChEBI
LIPOIC ACIDChEBI
S-LAChEBI
SLAChEBI
Thioctic acid L-formChEBI
(S)-(-)-LipoateGenerator
(S)-1,2-Dithiolane-3-pentanoateGenerator
(S)-a-LipoateGenerator
(S)-a-Lipoic acidGenerator
(S)-alpha-LipoateGenerator
(S)-Α-lipoateGenerator
(S)-Α-lipoic acidGenerator
L-1,2-Dithiolane 3-valerateGenerator
L-6,8-ThioctateGenerator
L-6-ThioctateGenerator
LIPOateGenerator
Thioctate L-formGenerator
(S)-LipoateGenerator
Acid, alpha-lipoicHMDB
Thioctic acidHMDB
alpha Lipoic acidHMDB
(-)-Thioctic acidHMDB
(3S)-1,2-Dithiolane-3-pentanoic acidHMDB
(S)-Thioctic acidHMDB
S-(-)-alpha-Lipoic acidHMDB
S-(-)-Α-lipoic acidHMDB
1,2-Dithiolane-3-valeric acidHMDB
1,2-Dithiolane-3-pentanoic acidHMDB
5-(1,2-Dithiolan-3-yl)pentanoic acidHMDB
5-(1,2-Dithiolan-3-yl)valeric acidHMDB
6,8-Thioctic acidHMDB
6-Thioctic acidHMDB
ALAHMDB
(S)-Lipoic acidHMDB
Chemical FormulaC8H14O2S2
Average Mass206.3260 Da
Monoisotopic Mass206.04352 Da
IUPAC Name5-[(3S)-1,2-dithiolan-3-yl]pentanoic acid
Traditional NameS-LA
CAS Registry NumberNot Available
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-/m0/s1
InChI KeyAGBQKNBQESQNJD-ZETCQYMHSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
Species
Species of Origin
Species NameSourceReference
Brassica oleracea var. italicaFooDB
Spinacia oleraceaFooDB
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point362.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility126.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.160 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
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
Polarizability21.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0014312
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID392857
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLipoic_acid
METLIN IDNot Available
PubChem Compound445125
PDB IDNot Available
ChEBI ID43796
Good Scents IDrw1543921
References
General References
  1. Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. doi: 10.1146/annurev.biochem.69.1.961. [PubMed:10966480 ]
  2. REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. doi: 10.1126/science.114.2952.93. [PubMed:14854913 ]
  3. Biewenga GP, Dorstijn MA, Verhagen JV, Haenen GR, Bast A: Reduction of lipoic acid by lipoamide dehydrogenase. Biochem Pharmacol. 1996 Feb 9;51(3):233-8. doi: 10.1016/0006-2952(95)02124-8. [PubMed:8573188 ]
  4. Loffelhardt S, Bonaventura C, Locher M, Borbe HO, Bisswanger H: Interaction of alpha-lipoic acid enantiomers and homologues with the enzyme components of the mammalian pyruvate dehydrogenase complex. Biochem Pharmacol. 1995 Aug 25;50(5):637-46. doi: 10.1016/0006-2952(95)00175-y. [PubMed:7669066 ]