MiMeDB: Showing metabocard for Sebacic acid (MMDBc0000547)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:40:15 UTC

Update Date

2024-04-30 19:32:57 UTC

Metabolite ID

MMDBc0000547

Metabolite Identification

Common Name

Sebacic acid

Description

Sebacic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms. Sebacic acid is a normal urinary acid. In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD), also known as glutaric aciduria type II (GAII), a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion. Sebacic acid is found to be associated with carnitine-acylcarnitine translocase deficiency and medium chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism. Sebacic acid is a white flake or powdered crystal slightly soluble in water that has been proposed as an alternative energy substrate in total parenteral nutrition. Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. Sebacic acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. It is used in the synthesis of polyamide and alkyd resins. It is also used as an intermediate for aromatics, antiseptics and painting materials (PMID: 10556649 , 1738216 , 8442769 , 12706375 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000792
     RDKit          3D
Sebacic acid
 32 31  0  0  0  0  0  0  0  0999 V2000
    5.1955   -0.5268   -2.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9214   -0.4396   -0.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7105   -0.9664   -0.0034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6631    0.2779   -0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6649   -0.7144   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3902   -0.0331    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    0.6116   -0.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650    1.3082   -0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5593    0.3298    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    1.0125    0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746    0.0870    1.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2845   -1.0359    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9131   -1.2930   -0.9694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2032   -1.9298    0.7520 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4477   -0.9082    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9988    0.9923    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2439    0.8253   -1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0882   -1.2834    0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4130   -1.4894   -0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162   -0.7929    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6361    0.7266    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3907    1.2799   -1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4561   -0.2076   -1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3098    2.1085    0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9628    1.8167   -1.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1388   -0.1967    0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972   -0.4493   -0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2306    1.6086   -0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5991    1.7554    1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8023    0.7103    1.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5297   -0.2419    2.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0448   -1.6272    1.2091 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 13  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
M  END

HMDB0000792
     RDKit          3D
Sebacic acid
 32 31  0  0  0  0  0  0  0  0999 V2000
    5.1955   -0.5268   -2.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9214   -0.4396   -0.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7105   -0.9664   -0.0034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6631    0.2779   -0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6649   -0.7144   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3902   -0.0331    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    0.6116   -0.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650    1.3082   -0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5593    0.3298    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    1.0125    0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746    0.0870    1.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2845   -1.0359    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9131   -1.2930   -0.9694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2032   -1.9298    0.7520 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4477   -0.9082    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9988    0.9923    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2439    0.8253   -1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0882   -1.2834    0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4130   -1.4894   -0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162   -0.7929    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6361    0.7266    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3907    1.2799   -1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4561   -0.2076   -1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3098    2.1085    0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9628    1.8167   -1.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1388   -0.1967    0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972   -0.4493   -0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2306    1.6086   -0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5991    1.7554    1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8023    0.7103    1.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5297   -0.2419    2.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0448   -1.6272    1.2091 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 13  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Sepiapterin.mol                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       6.002  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.668   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.334  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.001   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.334   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.668  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.002   0.385   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.002  -1.925   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.335   0.385   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -6.002   1.925   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -7.335  -0.385   0.000  0.00  0.00           O+0
CONECT    1    2   11   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   13   14                                                  
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13   10                                                            
CONECT   14   10                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0000792
HETATM    1  O1  UNL     1       5.196  -0.527  -2.195  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.921  -0.440  -0.991  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.711  -0.966  -0.003  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.663   0.278  -0.595  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.665  -0.714  -0.067  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.390  -0.033   0.342  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.746   0.612  -0.840  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.565   1.308  -0.465  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.559   0.330   0.102  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.867   1.013   0.449  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.875   0.087   1.033  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.285  -1.036   0.190  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.913  -1.293  -0.969  1.00  0.00           O  
HETATM   14  O4  UNL     1      -5.203  -1.930   0.752  1.00  0.00           O  
HETATM   15  H1  UNL     1       5.448  -0.908   0.968  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.999   0.992   0.196  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.244   0.825  -1.440  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.088  -1.283   0.801  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.413  -1.489  -0.823  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.716  -0.793   0.832  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.636   0.727   1.131  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.391   1.280  -1.409  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.456  -0.208  -1.560  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.310   2.109   0.261  1.00  0.00           H  
HETATM   25  H11 UNL     1      -0.963   1.817  -1.359  1.00  0.00           H  
HETATM   26  H12 UNL     1      -1.139  -0.197   0.982  1.00  0.00           H  
HETATM   27  H13 UNL     1      -1.797  -0.449  -0.676  1.00  0.00           H  
HETATM   28  H14 UNL     1      -3.231   1.609  -0.391  1.00  0.00           H  
HETATM   29  H15 UNL     1      -2.599   1.755   1.258  1.00  0.00           H  
HETATM   30  H16 UNL     1      -4.802   0.710   1.230  1.00  0.00           H  
HETATM   31  H17 UNL     1      -3.530  -0.242   2.047  1.00  0.00           H  
HETATM   32  H18 UNL     1      -6.045  -1.627   1.209  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8    9   24   25
CONECT    9   10   26   27
CONECT   10   11   28   29
CONECT   11   12   30   31
CONECT   12   13   13   14
CONECT   14   32
END

HMDB0000792
     RDKit          3D
Sebacic acid
 32 31  0  0  0  0  0  0  0  0999 V2000
    5.1955   -0.5268   -2.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9214   -0.4396   -0.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7105   -0.9664   -0.0034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6631    0.2779   -0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6649   -0.7144   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3902   -0.0331    0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    0.6116   -0.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650    1.3082   -0.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5593    0.3298    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    1.0125    0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746    0.0870    1.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2845   -1.0359    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9131   -1.2930   -0.9694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2032   -1.9298    0.7520 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4477   -0.9082    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9988    0.9923    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2439    0.8253   -1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0882   -1.2834    0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4130   -1.4894   -0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7162   -0.7929    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6361    0.7266    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3907    1.2799   -1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4561   -0.2076   -1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3098    2.1085    0.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9628    1.8167   -1.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1388   -0.1967    0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972   -0.4493   -0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2306    1.6086   -0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5991    1.7554    1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8023    0.7103    1.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5297   -0.2419    2.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0448   -1.6272    1.2091 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 13  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
M  END

Synonyms

Value	Source
1,10-Decanedioic acid	ChEBI
1,8-Dicarboxyoctane	ChEBI
Decanedioic acid	ChEBI
Sebacinsaeure	ChEBI
1,10-Decanedioate	Generator
Decanedioate	Generator
Sebacate	Generator
1,8-Octanedicarboxylate	HMDB
1,8-Octanedicarboxylic acid	HMDB
4,7-Dioxosebacic acid	HMDB
4-Oxodecanedioate	HMDB
4-Oxodecanedioic acid	HMDB
Acide sebacique	HMDB
Decanedicarboxylic acid	HMDB
Dicarboxylic acid C10	HMDB
Ipomic acid	HMDB
N-Decanedioate	HMDB
N-Decanedioic acid	HMDB
Sebacic acids	HMDB
Sebacinsaure	HMDB
Seracic acid	HMDB
Sebacic acid, aluminum salt	HMDB
Sebacic acid, monocadmium salt	HMDB
Sebacic acid, sodium salt	HMDB

Molecular Formula

C₁₀H₁₈O₄

Average Mass

202.2475

Monoisotopic Mass

202.120509064

IUPAC Name

decanedioic acid

Traditional Name

sebacic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)

InChI Key

CXMXRPHRNRROMY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,omega-dicarboxylic acid (CHEBI:41865 )
Dicarboxylic acids (C08277 )
Dicarboxylic acids (LMFA01170006 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.91 g/L	ALOGPS
logP	1.93	ALOGPS
logP	2.27	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	51.14 m³·mol⁻¹	ChemAxon
Polarizability	22.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00mk-2910000000-944d83241331f8be19a6	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00mk-1910000000-2e3fc1189a96874a25c9	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00fr-9400000000-d288a779699c505fde08	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00pj-3910000000-87feed2c593dbff7fae8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00mk-2910000000-944d83241331f8be19a6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00mk-1910000000-2e3fc1189a96874a25c9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00fr-9400000000-d288a779699c505fde08	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00pj-3910000000-87feed2c593dbff7fae8	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9600000000-0d93a938bd873800d5e0	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-9750000000-c51f62deffa53727f438	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0udi-0290000000-cd204cf662cb75a52f8c	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0540-5910000000-d9df3022a95972158b37	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0ue9-9660000000-49a78126c0d15f6e3eb7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0090000000-841b953970b4cd52f8be	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0uei-0950000000-001fe11fe26a2d644897	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-0900000000-83a69e4c3ab60df51781	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-08i9-7900000000-951787b9bed084d77a6b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-057i-9000000000-83b9d67dcdf5f385ab57	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0f80-0950000000-7fec916790f882e8630a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-841b953970b4cd52f8be	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0uei-0950000000-001fe11fe26a2d644897	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-83a69e4c3ab60df51781	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-08i9-7900000000-951787b9bed084d77a6b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-057i-9000000000-83b9d67dcdf5f385ab57	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0019-0900000000-e9711749ce4f183c8c63	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f80-0950000000-e264d8b786405e562fd4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-007d-8900000000-fb7880caeb9e996f8bba	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0uei-0960000000-b0edb62684a8bf743208	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0f80-0930000000-e6d1038fa517b1259227	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0970000000-b21ac000bbddcd19753b	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k9l-2910000000-aad49769e8652ff2ea40	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06rw-9200000000-bab98f63e58992b52316	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0290000000-f600fa6f22d1c40d97d5	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-2790000000-3f24f2c725d420658a66	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9300000000-1aa6408615ab7e415691	2017-07-26	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0532-9200000000-34e843efdffcce316afd	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0005313	Water	Hydrogen Ion	Alcohol dehydrogenase 5 (class iii), chi polypeptide	VMH	P.L. Frabetti et al. On the narrow dip structure at 1.9 GeV/c2 in diffractive photoproduction. Physics Letters B, Volume 578, Issues 3-4, 2004, Pages 290-296. DOI
MMDBr0005351	Adenosine triphosphate	Adenosine monophosphate	Not Available	VMH	18538142
MMDBr0005352	Sebacic acid	Sebacic acid	Not Available	VMH	30371894
MMDBr0005354	Water	Coenzyme A	Acyl-coa thioesterase 8	VMH	30371894
MMDBr0006070	Sebacic acid	Sebacic acid	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Carnitine-acylcarnitine translocase deficiency		Association	Human Urine	HMDB	1598097
Carnitine-acylcarnitine translocase deficiency		Association	Human Urine	HMDB	7472823
Medium chain acyl-coa dehydrogenase deficiency	Decreased	Association	Human Urine	HMDB	2380628
Medium chain acyl-coa dehydrogenase deficiency	Slight Increase	Association	Human Urine	HMDB	6616873
Eosinophilic esophagitis	Increased	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Carnitine-acylcarnitine translocase deficiency		Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Carnitine-acylcarnitine translocase deficiency	Increased	Association	Human Urine	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	10	Human feces; Human stool; Human appendix biopsy; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	8	Human stool; Human feces; Human mucosa; Human ; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	2	Human feces; Human urine; Human stool; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	1	Human ; Human feces; Human sputum; Human saliva; Human supragingival plaque; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	1				umol/mmol creatinine	Infant (0-1 year old)	Male	3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency	HMDB	29030856
Human Blood	Detected and Quantified			0.70	3.7	uM	Infant (0-1 year old)	Female	3-Hydroxydicarboxylic aciduria	HMDB	2308028
Human Urine	Detected and Quantified	94				umol/mmol creatinine	Newborn (0-30 days old)	Not Specified	Carnitine-acylcarnitine translocase deficiency	HMDB	1598097
Human Urine	Detected and Quantified			57	266	umol/mmol creatinine	Newborn (0-30 days old)	Both	Carnitine-acylcarnitine translocase deficiency	HMDB	7472823
Human Urine	Detected and Quantified	0				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	2380628
Human Urine	Detected and Quantified	0				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	2380628
Human Urine	Detected and Quantified	50.312				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	2380628
Human Urine	Detected and Quantified	275.596				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	2380628
Human Urine	Detected and Quantified	527.713				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	2380628
Human Urine	Detected and Quantified			3	112	umol/mmol creatinine	Children (1 - 13 years old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	6616873
Human Urine	Detected and Quantified	0				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	2380628
Human Urine	Detected and Quantified	0				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	2380628
Human Urine	Detected and Quantified	0				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	2380628
Human Urine	Detected and Quantified	1.9				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			1	4	umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	HMDB	6616873
Human Urine	Detected and Quantified	<8				umol/mmol creatinine	Not Specified	Not Specified	Normal	HMDB	29030856
Human Urine	Detected and Quantified			0	0.8	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	1.0	umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	HMDB	31963255
Human Urine	Detected and Quantified			0	1.8	umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	HMDB	31963255
Human Blood	Detected and Quantified	0.091		0.072	0.11	uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	2308028
Human Urine	Detected and Quantified	0.60	0.78			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Urine	Detected and Quantified	1.118	2.795			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	2380628
Human Feces	Detected and Quantified	11.0755	10.235			nmol/g wet feces	Not Specified	Not Specified	Normal	HMDB	19573517
Human Urine	Detected and Quantified			2.0	5.0	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	12706375
Human Urine	Detected and Quantified	3.565	3.385			umol/mmol creatinine	Adult (>18 years old)	Both		HMDB	9439441
Human Urine	Detected and Quantified	4.472	3.913			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	2380628
Human Urine	Detected and Quantified	9.5	12.8			umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	2380628
Human Urine	Detected and Quantified	9.503	12.857			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	2380628
Human Urine	Detected and Quantified	9.263	8.411			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	1.0		0.0	2.0	umol/mmol creatinine	Adult (>18 years old)	Both	Carnitine-acylcarnitine translocase deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified	161.5		57.0	266.0	umol/mmol creatinine	Children (1-13 years old)	Both	Carnitine-Acylcarnitine translocase deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified	4.493	2.271			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	<9.83				umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	9439441
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	19573517
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25670064
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000792

DrugBank ID

DB07645

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Sebacic_acid

METLIN ID

4240

PubChem Compound

5192

PDB ID

Not Available

ChEBI ID

41865

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Mingrone G, Tacchino RM, Castagneto M, Finotti E, Greco AV: Use of even-numbered carbon atom dicarboxylic salts in parenteral nutrition as fuel substrate. JPEN J Parenter Enteral Nutr. 1992 Jan-Feb;16(1):32-8. doi: 10.1177/014860719201600132. [PubMed:1738216 ]
Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. doi: 10.1016/0378-4347(91)80571-s. [PubMed:2026685 ]
Jakobs C, Sweetman L, Wadman SK, Duran M, Saudubray JM, Nyhan WL: Prenatal diagnosis of glutaric aciduria type II by direct chemical analysis of dicarboxylic acids in amniotic fluid. Eur J Pediatr. 1984 Jan;141(3):153-7. doi: 10.1007/BF00443213. [PubMed:6698061 ]
Gregersen N, Kolvraa S, Mortensen PB, Rasmussen K: C6-C10-dicarboxylic aciduria: biochemical considerations in relation to diagnosis of beta-oxidation defects. Scand J Clin Lab Invest Suppl. 1982;161:15-27. doi: 10.3109/00365518209168396. [PubMed:6959231 ]
Bertuzzi A, Finotti E, Mingrone G, Greco AV: Sebacic acid binding to human plasma albumin. Biochem Pharmacol. 1993 Feb 9;45(3):697-702. doi: 10.1016/0006-2952(93)90145-m. [PubMed:8442769 ]
Capristo E, Mingrone G, De Gaetano A, Addolorato G, Greco AV, Gasbarrini G: A new HPLC method for the direct analysis of triglycerides of dicarboxylic acids in biological samples. Clin Chim Acta. 1999 Nov;289(1-2):11-21. doi: 10.1016/s0009-8981(99)00145-x. [PubMed:10556649 ]
Fleming AB, Saltzman WM: Pharmacokinetics of the carmustine implant. Clin Pharmacokinet. 2002;41(6):403-19. doi: 10.2165/00003088-200241060-00002. [PubMed:12074689 ]
Curcoy A, Olsen RK, Ribes A, Trenchs V, Vilaseca MA, Campistol J, Osorio JH, Andresen BS, Gregersen N: Late-onset form of beta-electron transfer flavoprotein deficiency. Mol Genet Metab. 2003 Apr;78(4):247-9. doi: 10.1016/s1096-7192(03)00024-6. [PubMed:12706375 ]

Showing metabocard for Sebacic acid (MMDBc0000547)

MOL for #<Metabolite:0x00007fd0f2bb7298>

3D MOL for #<Metabolite:0x00007fd0f2bb7298>

3D SDF for #<Metabolite:0x00007fd0f2bb7298>

3D-SDF for #<Metabolite:0x00007fd0f2bb7298>

PDB for #<Metabolite:0x00007fd0f2bb7298>

3D PDB for #<Metabolite:0x00007fd0f2bb7298>

SMILES for #<Metabolite:0x00007fd0f2bb7298>

INCHI for #<Metabolite:0x00007fd0f2bb7298>

Structure for #<Metabolite:0x00007fd0f2bb7298>

3D Structure for #<Metabolite:0x00007fd0f2bb7298>