Showing metabocard for Lipoamide (MMDBc0029520)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:25:42 UTC
Update Date2024-04-30 19:36:59 UTC
Metabolite IDMMDBc0029520
Metabolite Identification
Common NameLipoamide
DescriptionLipoamide is a trivial name for 6,8-dithiooctanoic amide. It is 6,8-dithiooctanoic acid's functional form where the carboxyl group is attached to protein (or any other amine) by an amide linkage (containing -NH2) to an amino group. -- Wikipedia
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9238cf2700>


  Mrv1652305271900192D          

 12 12  0  0  0  0            999 V2000
    9.8950   -6.8097    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0700   -6.8097    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8225   -6.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4825   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1425   -6.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8438   -5.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5863   -6.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2875   -5.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9888   -6.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7313   -5.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4325   -6.0260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7313   -4.7885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  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 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9238cf2700>

HMDB0000962
     RDKit          3D
Lipoamide
 27 27  0  0  0  0  0  0  0  0999 V2000
    4.1624    0.3932    0.3891 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9855   -0.3873    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4768   -0.8403    1.3904 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012   -0.7180   -0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201   -1.4585   -0.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532   -0.7262   -0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040    0.5889   -0.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575    1.3606    0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7111    0.5610    0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7336    1.3152    0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9603    1.5255    2.5780 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411    1.6072    1.7917 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0428    0.1874   -0.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1539    1.2335    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9983   -1.3896   -1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1959    0.1981   -1.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355   -2.3879   -0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6114   -1.8158   -1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9579   -1.4079   -0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2238   -0.6851    1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4810    1.2487   -0.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191    0.3519   -1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6753    2.3193   -0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1130    0.4604   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6217   -0.4479    0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9421    2.3189    0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5985    0.6638    1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 13  1  0
  1 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9238cf2700>


  Mrv1652305271900192D          

 12 12  0  0  0  0            999 V2000
    9.8950   -6.8097    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0700   -6.8097    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8225   -6.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4825   -5.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1425   -6.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8438   -5.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5863   -6.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2875   -5.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9888   -6.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7313   -5.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4325   -6.0260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7313   -4.7885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  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 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029520

> <DATABASE_NAME>
MIME

> <SMILES>
NC(=O)CCCCC1CCSS1

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)

> <INCHI_KEY>
FCCDDURTIIUXBY-UHFFFAOYSA-N

> <FORMULA>
C8H15NOS2

> <MOLECULAR_WEIGHT>
205.341

> <EXACT_MASS>
205.059505487

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.384415060709664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(1,2-dithiolan-3-yl)pentanamide

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
1.3068367939999996

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.449049724883853

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3815647676501084

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
56.1936

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lipoamide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9238cf2700>

HMDB0000962
     RDKit          3D
Lipoamide
 27 27  0  0  0  0  0  0  0  0999 V2000
    4.1624    0.3932    0.3891 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9855   -0.3873    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4768   -0.8403    1.3904 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012   -0.7180   -0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201   -1.4585   -0.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532   -0.7262   -0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040    0.5889   -0.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575    1.3606    0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7111    0.5610    0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7336    1.3152    0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9603    1.5255    2.5780 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411    1.6072    1.7917 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0428    0.1874   -0.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1539    1.2335    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9983   -1.3896   -1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1959    0.1981   -1.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355   -2.3879   -0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6114   -1.8158   -1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9579   -1.4079   -0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2238   -0.6851    1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4810    1.2487   -0.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191    0.3519   -1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6753    2.3193   -0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1130    0.4604   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6217   -0.4479    0.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9421    2.3189    0.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5985    0.6638    1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 13  1  0
  1 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
M  END
Download

PDB for #<Metabolite:0x00007f9238cf2700>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  S   UNK     0      18.471 -12.711   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      16.931 -12.711   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      16.469 -11.249   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.701 -10.325   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.933 -11.249   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.242 -10.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.628 -11.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.937 -10.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.246 -11.249   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.632 -10.479   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      26.941 -11.249   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      25.632  -8.939   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
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 #<Metabolite:0x00007f9238cf2700>

COMPND    HMDB0000962
HETATM    1  N1  UNL     1       4.162   0.393   0.389  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.985  -0.387   0.308  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.477  -0.840   1.390  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.301  -0.718  -0.942  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.020  -1.459  -0.812  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.053  -0.726  -0.042  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.404   0.589  -0.687  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.458   1.361   0.039  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.711   0.561   0.102  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.734   1.315   0.918  1.00  0.00           C  
HETATM   11  S1  UNL     1      -2.960   1.526   2.578  1.00  0.00           S  
HETATM   12  S2  UNL     1      -0.941   1.607   1.792  1.00  0.00           S  
HETATM   13  H1  UNL     1       5.043   0.187  -0.121  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.154   1.233   1.000  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.998  -1.390  -1.524  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.196   0.198  -1.594  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.235  -2.388  -0.213  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.611  -1.816  -1.778  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.958  -1.408  -0.077  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.224  -0.685   1.002  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.481   1.249  -0.797  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.719   0.352  -1.731  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.675   2.319  -0.428  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.113   0.460  -0.909  1.00  0.00           H  
HETATM   25  H13 UNL     1      -2.622  -0.448   0.530  1.00  0.00           H  
HETATM   26  H14 UNL     1      -3.942   2.319   0.549  1.00  0.00           H  
HETATM   27  H15 UNL     1      -4.599   0.664   1.056  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3    3    4
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   12   23
CONECT    9   10   24   25
CONECT   10   11   26   27
CONECT   11   12
END
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SMILES for #<Metabolite:0x00007f9238cf2700>

NC(=O)CCCCC1CCSS1
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INCHI for #<Metabolite:0x00007f9238cf2700>

InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)
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Synonyms
ValueSource
1,2-Dithiolane-3-pentanamideChEBI
alpha-Lipoic acid amideChEBI
LipoacinChEBI
ThioctamideChEBI
Thioctic acid amideChEBI
Vitamin NChEBI
a-Lipoate amideGenerator
a-Lipoic acid amideGenerator
alpha-Lipoate amideGenerator
Α-lipoate amideGenerator
Α-lipoic acid amideGenerator
Thioctate amideGenerator
5-(1,2-Dithiolan-3-yl)-pentanamideHMDB
5-(1,2-Dithiolan-3-yl)pentanamideHMDB
5-(1,2-Dithiolan-3-yl)valeramideHMDB
5-(Dithiolan-3-yl)valeramideHMDB
alpha-LipoateHMDB
alpha-Lipoic acidHMDB
DL-6-Thioctic amideHMDB
DL-LipoamideHMDB
LipamideHMDB
LipoamidHMDB
LipoicinHMDB
LipozymeHMDB
LypoaranHMDB
PathoclonHMDB
ThioamiHMDB
ThioctamidHMDB
ThiotominHMDB
TicolinHMDB
1,2-Dithiolane-3-valeramideHMDB
6,8-Thioctic amideHMDB
alpha-Lipoic amideHMDB
Lipoamide, (+-)-isomerHMDB
Molecular FormulaC8H15NOS2
Average Mass205.341
Monoisotopic Mass205.059505487
IUPAC Name5-(1,2-dithiolan-3-yl)pentanamide
Traditional Namelipoamide
CAS Registry Number940-69-2
SMILES
NC(=O)CCCCC1CCSS1
InChI Identifier
InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)
InChI KeyFCCDDURTIIUXBY-UHFFFAOYSA-N