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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
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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

$$$$
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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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Synonyms
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 locationSource
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
Predicted Chromatographic Properties
Spectra
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 ]