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Showing metabocard for (S)-Lipoic acid (HMDB0014312)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:34 UTC
HMDB IDHMDB0014312
Secondary Accession Numbers
  • HMDB14312
Metabolite Identification
Common Name(S)-Lipoic acid
Description
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014312 ((S)-Lipoic acid)

  Mrv1652305211918002D          

 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  1  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
    3.4944    0.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2089    0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2089    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  6  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 HMDB0014312 ((S)-Lipoic acid)

HMDB0014312
     RDKit          3D
(S)-Lipoic acid
 26 26  0  0  0  0  0  0  0  0999 V2000
    1.8977    1.5825    1.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7745    1.2762    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7458    2.2204    0.2381 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8095   -0.0111   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7110   -0.9627    0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3293   -0.4533   -0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -1.4722    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1088   -1.1678   -0.2147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7311    0.0022    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4617    1.3104   -0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2512    1.1496   -1.9827 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3703   -0.9870   -2.0246 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5313    3.2063    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292    0.1025   -1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7704   -0.5227    0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6791   -1.1593    1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9271   -1.9116   -0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003    0.5043    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3806   -0.2105   -1.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853   -1.7184    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4173   -2.4300   -0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7552   -2.0585    0.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4214    0.0709    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8485   -0.1674    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4091    1.9259   -0.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6316    1.8813    0.2859 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
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3D SDF for HMDB0014312 ((S)-Lipoic acid)

  Mrv1652305211918002D          

 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  1  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
    3.4944    0.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2089    0.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2089    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  6  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>
HMDB0014312

> <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-/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 HMDB0014312 ((S)-Lipoic acid)

HMDB0014312
     RDKit          3D
(S)-Lipoic acid
 26 26  0  0  0  0  0  0  0  0999 V2000
    1.8977    1.5825    1.3543 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7745    1.2762    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7458    2.2204    0.2381 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8095   -0.0111   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7110   -0.9627    0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3293   -0.4533   -0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -1.4722    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1088   -1.1678   -0.2147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7311    0.0022    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4617    1.3104   -0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2512    1.1496   -1.9827 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3703   -0.9870   -2.0246 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5313    3.2063    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292    0.1025   -1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7704   -0.5227    0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6791   -1.1593    1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9271   -1.9116   -0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003    0.5043    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3806   -0.2105   -1.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853   -1.7184    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4173   -2.4300   -0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7552   -2.0585    0.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4214    0.0709    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8485   -0.1674    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4091    1.9259   -0.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6316    1.8813    0.2859 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
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PDB for HMDB0014312 ((S)-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
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3D PDB for HMDB0014312 ((S)-Lipoic acid)

COMPND    HMDB0014312
HETATM    1  O1  UNL     1       1.898   1.582   1.354  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.774   1.276   0.517  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.746   2.220   0.238  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.809  -0.011  -0.161  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.711  -0.963   0.142  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.329  -0.453  -0.233  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.694  -1.472   0.102  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.109  -1.168  -0.215  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.731   0.002   0.411  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.462   1.310  -0.190  1.00  0.00           C  
HETATM   11  S1  UNL     1      -2.251   1.150  -1.983  1.00  0.00           S  
HETATM   12  S2  UNL     1      -2.370  -0.987  -2.025  1.00  0.00           S  
HETATM   13  H1  UNL     1       3.531   3.206   0.083  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.929   0.102  -1.265  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.770  -0.523   0.157  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.679  -1.159   1.237  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.927  -1.912  -0.385  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.200   0.504   0.300  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.381  -0.210  -1.319  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.585  -1.718   1.191  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.417  -2.430  -0.424  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.755  -2.058   0.093  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.421   0.071   1.495  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.848  -0.167   0.447  1.00  0.00           H  
HETATM   25  H13 UNL     1      -3.409   1.926  -0.065  1.00  0.00           H  
HETATM   26  H14 UNL     1      -1.632   1.881   0.286  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 HMDB0014312 ((S)-Lipoic acid)

OC(=O)CCCC[C@H]1CCSS1
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INCHI for HMDB0014312 ((S)-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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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC8H14O2S2
Average Molecular Weight206.326
Monoisotopic Molecular Weight206.043521072
IUPAC Name5-[(3S)-1,2-dithiolan-3-yl]pentanoic acid
Traditional NameS-LA
CAS Registry Number1077-27-6
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
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 application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.22 g/LNot Available
LogP2.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00166 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00166 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. [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. [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 ]
  5. Streeper RS, Henriksen EJ, Jacob S, Hokama JY, Fogt DL, Tritschler HJ: Differential effects of lipoic acid stereoisomers on glucose metabolism in insulin-resistant skeletal muscle. Am J Physiol. 1997 Jul;273(1 Pt 1):E185-91. doi: 10.1152/ajpendo.1997.273.1.E185. [PubMed:9252495 ]

Enzymes

Enzyme Details
1. 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
References
  1. Dudka J: Decrease in NADPH-cytochrome P450 reductase activity of the human heart, Liver and lungs in the presence of alpha-lipoic acid. Ann Nutr Metab. 2006;50(2):121-5. Epub 2006 Jan 2. [PubMed:16391466 ]
  2. Wen B, Coe KJ, Rademacher P, Fitch WL, Monshouwer M, Nelson SD: Comparison of in vitro bioactivation of flutamide and its cyano analogue: evidence for reductive activation by human NADPH:cytochrome P450 reductase. Chem Res Toxicol. 2008 Dec;21(12):2393-406. doi: 10.1021/tx800281h. [PubMed:19548358 ]
  3. Gan L, von Moltke LL, Trepanier LA, Harmatz JS, Greenblatt DJ, Court MH: Role of NADPH-cytochrome P450 reductase and cytochrome-b5/NADH-b5 reductase in variability of CYP3A activity in human liver microsomes. Drug Metab Dispos. 2009 Jan;37(1):90-6. doi: 10.1124/dmd.108.023424. Epub 2008 Oct 6. [PubMed:18838505 ]
Enzyme Details
2. Lipoyl synthase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Catalyzes the radical-mediated insertion of two sulfur atoms into the C-6 and C-8 positions of the octanoyl moiety bound to the lipoyl domains of lipoate-dependent enzymes, thereby converting the octanoylated domains into lipoylated derivatives (By similarity).
Gene Name:
LIAS
Uniprot ID:
O43766
Molecular weight:
41910.695
References
  1. Morikawa T, Yasuno R, Wada H: Do mammalian cells synthesize lipoic acid? Identification of a mouse cDNA encoding a lipoic acid synthase located in mitochondria. FEBS Lett. 2001 Jun 1;498(1):16-21. [PubMed:11389890 ]
  2. Yasuno R, Wada H: Biosynthesis of lipoic acid in Arabidopsis: cloning and characterization of the cDNA for lipoic acid synthase. Plant Physiol. 1998 Nov;118(3):935-43. [PubMed:9808738 ]
  3. Ollagnier-de Choudens S, Fontecave M: The lipoate synthase from Escherichia coli is an iron-sulfur protein. FEBS Lett. 1999 Jun 18;453(1-2):25-8. [PubMed:10403368 ]
  4. Wrenger C, Muller S: The human malaria parasite Plasmodium falciparum has distinct organelle-specific lipoylation pathways. Mol Microbiol. 2004 Jul;53(1):103-13. [PubMed:15225307 ]
  5. Gunther S, McMillan PJ, Wallace LJ, Muller S: Plasmodium falciparum possesses organelle-specific alpha-keto acid dehydrogenase complexes and lipoylation pathways. Biochem Soc Trans. 2005 Nov;33(Pt 5):977-80. [PubMed:16246025 ]
Enzyme Details
3. Sodium-dependent multivitamin transporter
General function:
Involved in transporter activity
Specific function:
Transports pantothenate, biotin and lipoate in the presence of sodium.
Gene Name:
SLC5A6
Uniprot ID:
Q9Y289
Molecular weight:
68641.27
References
  1. Prasad PD, Wang H, Huang W, Fei YJ, Leibach FH, Devoe LD, Ganapathy V: Molecular and functional characterization of the intestinal Na+-dependent multivitamin transporter. Arch Biochem Biophys. 1999 Jun 1;366(1):95-106. [PubMed:10334869 ]
  2. Dey S, Subramanian VS, Chatterjee NS, Rubin SA, Said HM: Characterization of the 5' regulatory region of the human sodium-dependent multivitamin transporter, hSMVT. Biochim Biophys Acta. 2002 Mar 19;1574(2):187-92. [PubMed:11955628 ]
  3. Griffin JB, Stanley JS, Zempleni J: Synthesis of a rabbit polyclonal antibody to the human sodium-dependent multivitamin transporter. Int J Vitam Nutr Res. 2002 Jul;72(4):195-8. [PubMed:12214555 ]
Enzyme Details
4. Acyl-coenzyme A synthetase ACSM1, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro). Functions as GTP-dependent lipoate-activating enzyme that generates the substrate for lipoyltransferase (By similarity).
Gene Name:
ACSM1
Uniprot ID:
Q08AH1
Molecular weight:
65272.74
Reactions
Guanosine triphosphate + (S)-Lipoic acid → Pyrophosphate + lipoyl-GMPdetails
Enzyme Details
5. 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
References
  1. Gunther S, McMillan PJ, Wallace LJ, Muller S: Plasmodium falciparum possesses organelle-specific alpha-keto acid dehydrogenase complexes and lipoylation pathways. Biochem Soc Trans. 2005 Nov;33(Pt 5):977-80. [PubMed:16246025 ]
  2. Fujiwara K, Toma S, Okamura-Ikeda K, Motokawa Y, Nakagawa A, Taniguchi H: Crystal structure of lipoate-protein ligase A from Escherichia coli. Determination of the lipoic acid-binding site. J Biol Chem. 2005 Sep 30;280(39):33645-51. Epub 2005 Jul 25. [PubMed:16043486 ]
  3. Gueguen V, Macherel D, Neuburger M, Pierre CS, Jaquinod M, Gans P, Douce R, Bourguignon J: Structural and functional characterization of H protein mutants of the glycine decarboxylase complex. J Biol Chem. 1999 Sep 10;274(37):26344-52. [PubMed:10473591 ]
  4. Macherel D, Bourguignon J, Forest E, Faure M, Cohen-Addad C, Douce R: Expression, lipoylation and structure determination of recombinant pea H-protein in Escherichia coli. Eur J Biochem. 1996 Feb 15;236(1):27-33. [PubMed:8617275 ]
  5. Fujiwara K, Hosaka H, Matsuda M, Okamura-Ikeda K, Motokawa Y, Suzuki M, Nakagawa A, Taniguchi H: Crystal structure of bovine lipoyltransferase in complex with lipoyl-AMP. J Mol Biol. 2007 Aug 3;371(1):222-34. Epub 2007 May 26. [PubMed:17570395 ]