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Showing metabocard for Thioctic acid (HMDB0251530)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:53:35 UTC
Update Date2021-09-26 23:03:34 UTC
HMDB IDHMDB0251530
Secondary Accession NumbersNone
Metabolite Identification
Common NameThioctic acid
Descriptionlipoate, also known as lipoic acid or alpha-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. lipoate exists in all living organisms, ranging from bacteria to humans. In humans, lipoate is involved in the metabolic disorder called the glutaminolysis and cancer pathway. lipoate has been detected, but not quantified in, broccolis (Brassica oleracea var. italica) and spinaches (Spinacia oleracea). This could make lipoate a potential biomarker for the consumption of these foods. lipoate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on lipoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Thioctic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Thioctic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0251530 (Thioctic acid)


  Mrv0541 04191212102D          

 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  0  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  0  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 HMDB0251530 (Thioctic acid)

HMDB0251530
     RDKit          3D
Thioctic acid
 26 26  0  0  0  0  0  0  0  0999 V2000
    2.9898    1.5886    0.1063 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641    0.4380    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8460    0.3724    0.4123 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7446   -0.8256   -0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -0.5453   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    0.0720    0.9823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    0.4250    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7372   -0.6509    0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1641   -0.1464    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3162    0.8257   -0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225   -0.0304   -2.2277 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665   -1.4217   -1.1729 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4696    1.1263    0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -1.5200    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957   -1.2886   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0470    0.0935   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7550   -1.5303   -0.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786   -0.6879    1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496    0.9464    1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1187    0.8322    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996    1.3206    0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099   -1.4553    1.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3934    0.3334    1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8064   -1.0292    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058    1.0380   -0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7119    1.7194   -0.5932 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  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
M  END
Download

3D SDF for HMDB0251530 (Thioctic acid)


  Mrv0541 04191212102D          

 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  0  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  0  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>
HMDB0251530

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCCCC1CCSS1

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

> <INCHI_KEY>
AGBQKNBQESQNJD-UHFFFAOYSA-N

> <FORMULA>
C8H14O2S2

> <MOLECULAR_WEIGHT>
206.326

> <EXACT_MASS>
206.043521072

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.001838258546407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(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>
6,8-thioctic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0251530 (Thioctic acid)

HMDB0251530
     RDKit          3D
Thioctic acid
 26 26  0  0  0  0  0  0  0  0999 V2000
    2.9898    1.5886    0.1063 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641    0.4380    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8460    0.3724    0.4123 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7446   -0.8256   -0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -0.5453   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    0.0720    0.9823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    0.4250    0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7372   -0.6509    0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1641   -0.1464    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3162    0.8257   -0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225   -0.0304   -2.2277 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665   -1.4217   -1.1729 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4696    1.1263    0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -1.5200    0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957   -1.2886   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0470    0.0935   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7550   -1.5303   -0.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786   -0.6879    1.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496    0.9464    1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1187    0.8322    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996    1.3206    0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099   -1.4553    1.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3934    0.3334    1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8064   -1.0292    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058    1.0380   -0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7119    1.7194   -0.5932 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  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
M  END
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PDB for HMDB0251530 (Thioctic acid)

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         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 HMDB0251530 (Thioctic acid)

COMPND    HMDB0251530
HETATM    1  O1  UNL     1       2.990   1.589   0.106  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.464   0.438   0.140  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.846   0.372   0.412  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.745  -0.826  -0.070  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.251  -0.545  -0.243  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.653   0.072   0.982  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.788   0.425   0.805  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.737  -0.651   0.482  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.164  -0.146   0.394  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.316   0.826  -0.709  1.00  0.00           C  
HETATM   11  S1  UNL     1      -2.722  -0.030  -2.228  1.00  0.00           S  
HETATM   12  S2  UNL     1      -1.466  -1.422  -1.173  1.00  0.00           S  
HETATM   13  H1  UNL     1       5.470   1.126   0.220  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.896  -1.520   0.757  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.096  -1.289  -1.037  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.047   0.094  -1.114  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.755  -1.530  -0.438  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.779  -0.688   1.817  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.250   0.946   1.352  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.119   0.832   1.820  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.900   1.321   0.126  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.710  -1.455   1.206  1.00  0.00           H  
HETATM   23  H11 UNL     1      -3.393   0.333   1.352  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.806  -1.029   0.273  1.00  0.00           H  
HETATM   25  H13 UNL     1      -4.406   1.038  -0.805  1.00  0.00           H  
HETATM   26  H14 UNL     1      -2.712   1.719  -0.593  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 HMDB0251530 (Thioctic acid)

OC(=O)CCCCC1CCSS1
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INCHI for HMDB0251530 (Thioctic acid)

InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,2-Dithiolane-3-pentanoic acidChEBI
1,2-Dithiolane-3-valeric acidChEBI
5-(1,2-Dithiolan-3-yl)valeric acidChEBI
5-(Dithiolan-3-yl)valeric acidChEBI
5-[3-(1,2-Dithiolanyl)]pentanoic acidChEBI
6,8-Thioctic acidChEBI
6,8-Thiotic acidChEBI
6-Thioctic acidChEBI
6-Thiotic acidChEBI
Acetate-replacing factorChEBI
alpha-Lipoic acidChEBI
alpha-LiponsaeureChEBI
BiletanChEBI
Liponic acidChEBI
ThioctansaeureChEBI
Thioctic acidChEBI
ThioctsaeureChEBI
ThioktsaeureChEBI
ThiotominKegg
Lipoic acidKegg
DL-alpha-Lipoic acidKegg
DL-Thioctic acidKegg
1,2-Dithiolane-3-pentanoateGenerator
1,2-Dithiolane-3-valerateGenerator
5-(1,2-Dithiolan-3-yl)valerateGenerator
5-(Dithiolan-3-yl)valerateGenerator
5-[3-(1,2-Dithiolanyl)]pentanoateGenerator
6,8-ThioctateGenerator
6,8-ThiotateGenerator
6-ThioctateGenerator
6-ThiotateGenerator
Acetic acid-replacing factorGenerator
a-LipoateGenerator
a-Lipoic acidGenerator
alpha-LipoateGenerator
Α-lipoateGenerator
Α-lipoic acidGenerator
a-LiponsaeureGenerator
Α-liponsaeureGenerator
LiponateGenerator
ThioctateGenerator
DL-a-LipoateGenerator
DL-a-Lipoic acidGenerator
DL-alpha-LipoateGenerator
DL-Α-lipoateGenerator
DL-Α-lipoic acidGenerator
DL-ThioctateGenerator
Acid, alpha-lipoicMeSH
Alpha LipogammaMeSH
Alpha Lipon stadaMeSH
Alpha Liponsaure sofotecMeSH
Alpha Lippon alMeSH
Alpha-LipogammaMeSH
Alpha-Lipon stadaMeSH
Alpha-Liponsaure sofotecMeSH
Alpha-Lippon alMeSH
AlphaLipogammaMeSH
AlphaLipon stadaMeSH
AlphaLiponsaure sofotecMeSH
AlphaLippon alMeSH
AlphaflamMeSH
AzulipontMeSH
FenintMeSH
Injekt, thiogammaMeSH
JuthiacMeSH
Liponsaure ratiopharmMeSH
Liponsaure-ratiopharmMeSH
LiponsaureratiopharmMeSH
MTW AlphaliponsaureMeSH
MTW-AlphaliponsaureMeSH
MTWAlphaliponsaureMeSH
NeuriumMeSH
Pleomix AlphaMeSH
Pleomix Alpha NMeSH
Pleomix-AlphaMeSH
Pleomix-Alpha NMeSH
PleomixAlphaMeSH
PleomixAlpha NMeSH
ThioctacidMeSH
Thioctacide TMeSH
Thiogamma injektMeSH
Thiogamma oralMeSH
TromliponMeSH
Verla liponMeSH
Verla-liponMeSH
VerlaLiponMeSH
alpha Lipoic acidMeSH
alpha Liponaure heumannMeSH
alpha Liponsaure von CTMeSH
alpha VibolexMeSH
alpha-Liponaure heumannMeSH
alpha-Liponsaure von CTMeSH
alpha-VibolexMeSH
AlphaLiponaure heumannMeSH
AlphaLiponsaure von CTMeSH
AlphaVibolexMeSH
Biomo liponMeSH
Biomo-liponMeSH
BiomoliponMeSH
DuraliponMeSH
Espa liponMeSH
Espa-liponMeSH
EspaliponMeSH
(R)-LipoateGenerator
Generosan brand OF thioctic acidMeSH
Merck dura brand OF thioctic acidMeSH
Rosen brand OF thioctic acidMeSH
Trommsdorgg brand OF thioctic acidMeSH
Viatris brand OF thioctic acid tromethamineMeSH
Esparma brand OF thioctic acidMeSH
Hexal brand OF thioctic acidMeSH
Stadapharm brand OF thioctic acidMeSH
Viatris brand OF thioctic acidMeSH
Ratiopharm brand OF thioctic acidMeSH
Aliud brand OF thioctic acidMeSH
Illa brand OF thioctic acidMeSH
Illa brand OF thioctic acid tromethamineMeSH
MTW Brand OF thioctic acidMeSH
Pharmacia brand OF thioctic acidMeSH
Q Pharm brand OF thioctic acidMeSH
Q-Pharm brand OF thioctic acidMeSH
Azupharma brand OF thioctic acidMeSH
Heumann brand OF thioctic acidMeSH
Juta brand OF thioctic acidMeSH
Lichtenstein brand OF thioctic acidMeSH
Sofotec brand OF thioctic acidMeSH
Verla brand OF thioctic acidMeSH
Worwag brand OF thioctic acidMeSH
Worwag brand OF thioctic acid meglumineMeSH
biomo Brand OF thioctic acidMeSH
CT Arzneimittel brand OF thioctic acidMeSH
CT-Arzneimittel brand OF thioctic acidMeSH
Chemical FormulaC8H14O2S2
Average Molecular Weight206.326
Monoisotopic Molecular Weight206.043521072
IUPAC Name5-(1,2-dithiolan-3-yl)pentanoic acid
Traditional Name6,8-thioctic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCCCC1CCSS1
InChI Identifier
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
InChI KeyAGBQKNBQESQNJD-UHFFFAOYSA-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 location
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability22 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
DeepCCS[M+H]+146.1930932474
DeepCCS[M-H]-143.67530932474
DeepCCS[M-2H]-179.41530932474
DeepCCS[M+Na]+154.7930932474
AllCCS[M+H]+143.532859911
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
Thioctic acidOC(=O)CCCCC1CCSS13009.2Standard polar33892256
Thioctic acidOC(=O)CCCCC1CCSS11757.1Standard non polar33892256
Thioctic acidOC(=O)CCCCC1CCSS11858.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Thioctic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4900000000-59fc063b5aa5a8b5db192021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thioctic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thioctic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thioctic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioctic acid 10V, Negative-QTOFsplash10-00di-0900000000-50da42c94591e9a60c0f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioctic acid 20V, Negative-QTOFsplash10-004i-0900000000-1346e3a528dca0514cf72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioctic acid 90V, Negative-QTOFsplash10-03di-9000000000-420a38a26d85b4091edb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioctic acid 75V, Negative-QTOFsplash10-03di-9000000000-24b63eebe2fd067ce4b82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioctic acid 15V, Negative-QTOFsplash10-0229-6900000000-44bcc93e18aeabd9ee162021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioctic acid 30V, Negative-QTOFsplash10-03k9-9600000000-4f680dfeae7fa1ece57a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioctic acid 45V, Negative-QTOFsplash10-03di-9000000000-6f0b91016a33e202e49b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thioctic acid 60V, Negative-QTOFsplash10-03di-9000000000-e3d4a7fe022cf20db0362021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 10V, Positive-QTOFsplash10-052r-0920000000-cf913d1d1afc04e5450c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 20V, Positive-QTOFsplash10-0bti-5910000000-294c510229247ef63f202015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 40V, Positive-QTOFsplash10-0bvi-9600000000-f8f54eb79c5d4d5bef482015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 10V, Negative-QTOFsplash10-0a4i-0920000000-5a823a30dd1fb434e5b12015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 20V, Negative-QTOFsplash10-0kmu-1910000000-6f491a68afd82922e71b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 40V, Negative-QTOFsplash10-0a4i-9200000000-330e4766f82ed571497b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 10V, Positive-QTOFsplash10-0a4r-0970000000-0ae5b11a032d11c1ba6d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 20V, Positive-QTOFsplash10-03di-1900000000-decf255617c1bbd69bfb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 40V, Positive-QTOFsplash10-000i-6900000000-eb58a3d8135ba85d42832021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 10V, Negative-QTOFsplash10-0a4i-0190000000-014d2ea36cfae0726a9e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 20V, Negative-QTOFsplash10-0a4i-5950000000-4e2dd5ccdcd5b0a936a02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thioctic acid 40V, Negative-QTOFsplash10-0a59-9500000000-9bbbd7b252fb9a0b438d2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004339
KNApSAcK IDC00041416
Chemspider ID841
KEGG Compound IDC00725
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLipoic_acid
METLIN IDNot Available
PubChem Compound864
PDB IDNot Available
ChEBI ID16494
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1582041
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]