Showing metabocard for lipoate (MMDBc0031142)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:36:57 UTC
Update Date2024-04-30 19:50:46 UTC
Metabolite IDMMDBc0031142
Metabolite Identification
Common Namelipoate
DescriptionA thia fatty acid anion that is the conjugate base of lipoic acid; major species at pH 7.3.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fece7dc76a8>


  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 #<Metabolite:0x00007fece7dc76a8>

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 #<Metabolite:0x00007fece7dc76a8>


  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>
MMDBc0031142

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fece7dc76a8>

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

PDB for #<Metabolite:0x00007fece7dc76a8>

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
Download

3D PDB for #<Metabolite:0x00007fece7dc76a8>

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
Download

SMILES for #<Metabolite:0x00007fece7dc76a8>

OC(=O)CCCCC1CCSS1
Download

INCHI for #<Metabolite:0x00007fece7dc76a8>

InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
Download
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
Molecular FormulaC8H14O2S2
Average Mass206.326
Monoisotopic Mass206.043521072
IUPAC Name5-(1,2-dithiolan-3-yl)pentanoic acid
Traditional Name6,8-thioctic acid
CAS Registry Number62-46-4
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