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enzymes (5) Show 5 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:03 UTC

HMDB ID

HMDB0000511

Secondary Accession Numbers

HMDB00511

Metabolite Identification

Common Name

Capric acid

Description

Capric acid, also known as decanoic acid is a C10 saturated fatty acid. It is a member of the series of fatty acids found in oils and animal fats. The names of caproic, caprylic, and capric acids are all derived from the word caper (Latin for goat). These fatty acids are light yellowish transparent oily liquids with a sweaty, unpleasant aroma that is reminiscent of goats. Capric acid is used in the manufacture of esters for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. Capric acid is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals. Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils. It is found in the milk of various mammals and to a lesser extent in other animal fats. Capric acid, caproic acid (a C6:0 fatty acid) and caprylic acid (a C8:0 fatty acid) account for about 15% of the fatty acids in goat milk fat (PMID 16747831 ). Capric acid may be responsible for the mitochondrial proliferation associated with the ketogenic diet, which may occur via PPARgamma receptor agonism and the targeting of genes involved in mitochondrial biogenesis (PMIDL 24383952).

Structure

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

HMDB0000511
     RDKit          3D
Capric acid
 32 31  0  0  0  0  0  0  0  0999 V2000
   -4.0296    0.8224   -1.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8987   -0.5392   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -0.4244    0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271    0.0592    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9373   -0.8648   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550   -0.4086   -0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522   -0.3005    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7134    0.1662   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7057    0.3152    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919    0.7681    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0188    0.9809    1.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1087    0.9760   -0.8918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428    1.5770   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630    0.8839   -1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    0.9629   -1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4674   -1.2217   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9130   -0.9001   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8840   -1.4769    1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4797    0.1407    1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550    1.0525    0.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    0.1341    1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8998   -1.9086   -0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977   -0.8616   -1.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388    0.5936   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962   -1.1920   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5298   -1.2880    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885    0.3906    1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886    1.1360   -0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -0.5968   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8238   -0.6196    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850    1.1166    1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5898    0.5269   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
M  END

HMDB0000511
     RDKit          3D
Capric acid
 32 31  0  0  0  0  0  0  0  0999 V2000
   -4.0296    0.8224   -1.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8987   -0.5392   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -0.4244    0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271    0.0592    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9373   -0.8648   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550   -0.4086   -0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522   -0.3005    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7134    0.1662   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7057    0.3152    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919    0.7681    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0188    0.9809    1.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1087    0.9760   -0.8918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428    1.5770   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630    0.8839   -1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    0.9629   -1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4674   -1.2217   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9130   -0.9001   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8840   -1.4769    1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4797    0.1407    1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550    1.0525    0.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    0.1341    1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8998   -1.9086   -0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977   -0.8616   -1.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388    0.5936   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962   -1.1920   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5298   -1.2880    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885    0.3906    1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886    1.1360   -0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -0.5968   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8238   -0.6196    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850    1.1166    1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5898    0.5269   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
M  END

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.669   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.670   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
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   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0000511
HETATM    1  C1  UNL     1      -4.030   0.822  -1.013  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.899  -0.539  -0.336  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.013  -0.424   0.886  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.627   0.059   0.540  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.937  -0.865  -0.406  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.455  -0.409  -0.768  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.352  -0.301   0.445  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.713   0.166  -0.070  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.706   0.315   1.042  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.992   0.768   0.460  1.00  0.00           C  
HETATM   11  O1  UNL     1       6.019   0.981   1.155  1.00  0.00           O  
HETATM   12  O2  UNL     1       5.109   0.976  -0.892  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.743   1.577  -0.261  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.363   0.884  -1.880  1.00  0.00           H  
HETATM   15  H3  UNL     1      -5.068   0.963  -1.383  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.467  -1.222  -1.082  1.00  0.00           H  
HETATM   17  H5  UNL     1      -4.913  -0.900  -0.032  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.884  -1.477   1.261  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.480   0.141   1.692  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.755   1.052   0.050  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.040   0.134   1.478  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.900  -1.909  -0.072  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.498  -0.862  -1.387  1.00  0.00           H  
HETATM   24  H12 UNL     1       0.439   0.594  -1.248  1.00  0.00           H  
HETATM   25  H13 UNL     1       0.896  -1.192  -1.419  1.00  0.00           H  
HETATM   26  H14 UNL     1       1.530  -1.288   0.917  1.00  0.00           H  
HETATM   27  H15 UNL     1       0.988   0.391   1.203  1.00  0.00           H  
HETATM   28  H16 UNL     1       2.589   1.136  -0.593  1.00  0.00           H  
HETATM   29  H17 UNL     1       3.030  -0.597  -0.807  1.00  0.00           H  
HETATM   30  H18 UNL     1       3.824  -0.620   1.632  1.00  0.00           H  
HETATM   31  H19 UNL     1       3.385   1.117   1.747  1.00  0.00           H  
HETATM   32  H20 UNL     1       4.590   0.527  -1.614  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6   22   23
CONECT    6    7   24   25
CONECT    7    8   26   27
CONECT    8    9   28   29
CONECT    9   10   30   31
CONECT   10   11   11   12
CONECT   12   32
END

HMDB0000511
     RDKit          3D
Capric acid
 32 31  0  0  0  0  0  0  0  0999 V2000
   -4.0296    0.8224   -1.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8987   -0.5392   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126   -0.4244    0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271    0.0592    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9373   -0.8648   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550   -0.4086   -0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522   -0.3005    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7134    0.1662   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7057    0.3152    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919    0.7681    0.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0188    0.9809    1.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1087    0.9760   -0.8918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428    1.5770   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630    0.8839   -1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    0.9629   -1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4674   -1.2217   -1.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9130   -0.9001   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8840   -1.4769    1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4797    0.1407    1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550    1.0525    0.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    0.1341    1.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8998   -1.9086   -0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977   -0.8616   -1.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388    0.5936   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8962   -1.1920   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5298   -1.2880    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885    0.3906    1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886    1.1360   -0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -0.5968   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8238   -0.6196    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850    1.1166    1.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5898    0.5269   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Nonanecarboxylic acid	ChEBI
10:0	ChEBI
C10:0	ChEBI
Caprinic acid	ChEBI
CH3-[CH2]8-COOH	ChEBI
Decanoate	ChEBI
Decoic acid	ChEBI
Decylic acid	ChEBI
Dekansaeure	ChEBI
Kaprinsaeure	ChEBI
N-Capric acid	ChEBI
N-Decanoic acid	ChEBI
N-Decoic acid	ChEBI
N-Decylic acid	ChEBI
1-Nonanecarboxylate	Generator
Caprinate	Generator
Decanoic acid	Generator
Decoate	Generator
Decylate	Generator
N-Caprate	Generator
N-Decanoate	Generator
N-Decoate	Generator
N-Decylate	Generator
Caprate	Generator
Caprynate	HMDB
Caprynic acid	HMDB
Emery 659	HMDB
Lunac 10-95	HMDB
Lunac 10-98	HMDB
Prifac 2906	HMDB
Prifac 296	HMDB
Decanoic acid, sodium salt	HMDB
Sodium caprate	HMDB
Sodium decanoate	HMDB
FA(10:0)	HMDB

Chemical Formula

C₁₀H₂₀O₂

Average Molecular Weight

172.2646

Monoisotopic Molecular Weight

172.146329884

IUPAC Name

decanoic acid

Traditional Name

capric acid

CAS Registry Number

334-48-5

SMILES

CCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)

InChI Key

GHVNFZFCNZKVNT-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
Straight chain fatty acid
Monocarboxylic 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

medium-chain fatty acid (CHEBI:30813 )
straight-chain saturated fatty acid (CHEBI:30813 )
Straight chain fatty acids (C01571 )
Saturated fatty acids (C01571 )
Straight chain fatty acids (LMFA01010010 )

Ontology

Physiological effect

Adverse health effect

Digestive system disorder

Gastrointestinal disorder

Upper GI Disorder

Eosinophilic esophagitis (PMID: 17334708 , PMID: 32966057 , PMID: 22623390 , +128

Source	Link
Pubmed	PMID: 17334708
Pubmed	PMID: 32966057
Pubmed	PMID: 22623390
Pubmed	PMID: 16870009
Pubmed	PMID: 26910390
Pubmed	PMID: 8087979
Pubmed	PMID: 25105552
Pubmed	PMID: 17349089
Pubmed	PMID: 24023812
Pubmed	PMID: 12376931
Pubmed	PMID: 15992788
Pubmed	PMID: 24341803
Pubmed	PMID: 19468821
Pubmed	PMID: 9625050
Pubmed	PMID: 2420598
Pubmed	PMID: 27012787
Pubmed	PMID: 30830347
Pubmed	PMID: 19551947
Pubmed	PMID: 19309105
Pubmed	PMID: 2026685
Pubmed	PMID: 5727921
Pubmed	PMID: 22024767
Pubmed	PMID: 17031479
Pubmed	PMID: 9439441
Pubmed	PMID: 9625050
Pubmed	PMID: 28649521
Pubmed	PMID: 28649521
Pubmed	PMID: 12097436
Pubmed	PMID: 8257730
Pubmed	PMID: 3168222
Pubmed	PMID: 9869364
Pubmed	PMID: 3436096
Pubmed	PMID: 22157537
Pubmed	PMID: 1246461
Pubmed	PMID: 25691415
Pubmed	PMID: 18004736
Pubmed	PMID: 31506554
Pubmed	PMID: 20423563
Pubmed	PMID: 25536744
Pubmed	PMID: 21388201
Pubmed	PMID: 4903899
Pubmed	PMID: 14708889
Pubmed	PMID: 14967154
Pubmed	PMID: 6774165
Pubmed	PMID: 21389975
Pubmed	PMID: 3709568
Pubmed	PMID: 8311084
Pubmed	PMID: 2242313
Pubmed	PMID: 20549362
Pubmed	PMID: 12555941
Pubmed	PMID: 10731506
Pubmed	PMID: 28157703
Pubmed	PMID: 20576202
Pubmed	PMID: 12368406
Pubmed	PMID: 26066683
Pubmed	PMID: 16736096
Pubmed	PMID: 25597510
Pubmed	PMID: 22800120
Pubmed	PMID: 16139832
Pubmed	PMID: 17287286
Pubmed	PMID: 17301081
Pubmed	PMID: 30817767
Pubmed	PMID: 25851806
Pubmed	PMID: 2587127
Pubmed	PMID: 11893004
Pubmed	PMID: 10102904
Pubmed	PMID: 23430553
Pubmed	PMID: 12705346
Pubmed	PMID: 19075476
Pubmed	PMID: 3571488
Pubmed	PMID: 7776094
Pubmed	PMID: 31963255
Pubmed	PMID: 23093139
Pubmed	PMID: 22284503
Pubmed	PMID: 8503438
Pubmed	PMID: 1246461
Pubmed	PMID: 20502474
Pubmed	PMID: 15558695
Pubmed	PMID: 422265
Pubmed	PMID: 22308371
Pubmed	PMID: 20549362
Pubmed	PMID: 9177981
Pubmed	PMID: 16828325
Pubmed	PMID: 16460720
Pubmed	PMID: 28157703
Pubmed	PMID: 8487492
Pubmed	PMID: 23890588
Pubmed	PMID: 14586528
Pubmed	PMID: 12927681
Pubmed	PMID: 9686366
Pubmed	PMID: 9029640
Pubmed	PMID: 22148915
Pubmed	PMID: 27123458
Pubmed	PMID: 20971021
Pubmed	PMID: 3169394
Pubmed	PMID: 21670092
Pubmed	PMID: 23363473
Pubmed	PMID: 15519880
Pubmed	PMID: 2380628
Pubmed	PMID: 6616873
Pubmed	PMID: 1870421
Pubmed	PMID: 19754154
Pubmed	PMID: 9857238
Pubmed	PMID: 12771321
Pubmed	PMID: 2702744
Pubmed	PMID: 9554495
Pubmed	PMID: 19033659
Pubmed	PMID: 19033659
Pubmed	PMID: 22887155
Pubmed	PMID: 17474139
Pubmed	PMID: 18953024
Pubmed	PMID: 6774165
Pubmed	PMID: 11052553
Pubmed	PMID: 16939360
Pubmed	PMID: 22827565
Pubmed	PMID: 21736852
Pubmed	PMID: 12661026
Pubmed	PMID: 18818040
Pubmed	PMID: 23770102
Pubmed	PMID: 15651030
Pubmed	PMID: 11307586
Pubmed	PMID: 21389975
Pubmed	PMID: 1640293
Pubmed	PMID: 25712379
Pubmed	PMID: 23770102
Pubmed	PMID: 24390407
Pubmed	PMID: 26709303
Pubmed	PMID: 3354621
Pubmed	PMID: 29030856
Pubmed	PMID: 12706375
Pubmed	PMID: 9869358

)

Disposition

Biological location

Cellular substructure

Extracellular

Non-excretory biofluid

Excreta

Tissue

Epithelium

Epidermis

Organ

Placenta

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	31.9 °C	Not Available
Boiling Point	268.00 to 270.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.062 mg/mL	Not Available
LogP	4.09	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	146.872	30932474
[M-H]-	Not Available	146.872	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000196

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.095 g/L	ALOGPS
logP	3.93	ALOGPS
logP	3.59	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	49.48 m³·mol⁻¹	ChemAxon
Polarizability	21.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	143.198	31661259
DarkChem	[M-H]-	140.25	31661259
AllCCS	[M+H]+	143.806	32859911
AllCCS	[M-H]-	145.06	32859911
DeepCCS	[M+H]+	148.09	30932474
DeepCCS	[M-H]-	144.89	30932474
DeepCCS	[M-2H]-	181.714	30932474
DeepCCS	[M+Na]+	156.901	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Capric acid	CCCCCCCCCC(O)=O	2238.6	Standard polar	33892256
Capric acid	CCCCCCCCCC(O)=O	1349.1	Standard non polar	33892256
Capric acid	CCCCCCCCCC(O)=O	1385.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Capric acid,1TMS,isomer #1	CCCCCCCCCC(=O)O[Si](C)(C)C	1453.2	Semi standard non polar	33892256
Capric acid,1TBDMS,isomer #1	CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	1678.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Capric acid GC-MS (1 TMS)	splash10-017i-2920000000-7f6721f01b80a790d544	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Capric acid EI-B (Non-derivatized)	splash10-076u-9000000000-96a2e9e00e464db3c086	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Capric acid GC-MS (Non-derivatized)	splash10-017i-2920000000-7f6721f01b80a790d544	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Capric acid GC-EI-TOF (Non-derivatized)	splash10-016r-1910000000-1cc1026f6f325d994ab4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-052g-9200000000-71a57b0e200e46fb66ed	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capric acid GC-MS (1 TMS) - 70eV, Positive	splash10-00g0-9300000000-c615f39c0b907a00f67c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capric acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-074l-9100000000-bf788cb34c09c6af56bf	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-0900000000-0a7f944302bce161f7e5	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00b9-1900000000-b68efbceecf3433a9995	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-005a-9600000000-f2a54ed1a56ee9b7af77	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid EI-B (HITACHI M-80B) , Positive-QTOF	splash10-076u-9000000000-96a2e9e00e464db3c086	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-00di-0900000000-771e7907916bf05e6b10	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-00di-0900000000-f1e000384728ee06f802	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-00di-1900000000-42a901bb54546da030da	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-004i-9000000000-83e77de04461ded1c4bc	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-004i-9000000000-f3190b828218d04d3cc7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid ESI-TOF 10V, Negative-QTOF	splash10-014i-0000000910-e82208ed71b4a3735258	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid ESI-TOF , Negative-QTOF	splash10-00di-0900000000-6ec01ce9b8fdc68d94a9	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid ESI-TOF 20V, Negative-QTOF	splash10-00di-0900000000-6ec01ce9b8fdc68d94a9	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Capric acid ESI-TOF 10V, Negative-QTOF	splash10-00di-0900000000-8c6cdf0491f51ba6ef26	2017-09-12	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 10V, Positive-QTOF	splash10-0a4i-0900000000-856f34ef153b15cb3d1d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 20V, Positive-QTOF	splash10-0adi-4900000000-efb0bd73973bf0c317fd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 40V, Positive-QTOF	splash10-052f-9000000000-d81148541fa575d32552	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 10V, Negative-QTOF	splash10-00di-0900000000-99cd0519b210c46b4a4c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 20V, Negative-QTOF	splash10-0fmi-1900000000-209285ec682ca47e1e5d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 40V, Negative-QTOF	splash10-0a4l-9300000000-fb697080d761d0f48fe2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 10V, Positive-QTOF	splash10-0a4i-0900000000-856f34ef153b15cb3d1d	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 20V, Positive-QTOF	splash10-0adi-4900000000-efb0bd73973bf0c317fd	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 40V, Positive-QTOF	splash10-052f-9000000000-d81148541fa575d32552	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 10V, Negative-QTOF	splash10-00di-0900000000-99cd0519b210c46b4a4c	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 20V, Negative-QTOF	splash10-0fmi-1900000000-209285ec682ca47e1e5d	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capric acid 40V, Negative-QTOF	splash10-0a4l-9300000000-fb697080d761d0f48fe2	2015-05-27	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Breast Milk
Feces
Saliva
Sweat
Urine

Tissue Locations

Epidermis
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Biosynthesis of unsaturated fatty acids	Not Available
Fatty Acid Biosynthesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	11.0 (5.0-17.0) uM	Adult (>18 years old)	Both	Normal	8412012	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Breast Milk	Detected and Quantified	53.7 +/- 19.3 uM	Adult (>18 years old)	Female	Normal	24027187	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected and Quantified	10.607 +/- 3.815 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Metastatic melanoma	28923537	details
Sweat	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	screen-positive CF	Adriana Nori...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Breast cancer	22284503	details
Urine	Detected and Quantified	9.517 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Metastatic melanoma
Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Cystic fibrosis
Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]
Perillyl alcohol administration for cancer treatment
Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
219700 (Cystic fibrosis)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB03600

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Decanoic acid

METLIN ID

336

PubChem Compound

2969

PDB ID

Not Available

ChEBI ID

30813

Food Biomarker Ontology

Not Available

VMH ID

DCA

MarkerDB ID

Not Available

Good Scents ID

rw1007741

References

Synthesis Reference

Wang, Qin; Ni, Xindi; Shi, Jianying. Manufacturing technology of capric acid and hydroxyalkyl amide from Litsea cubeba nucleolus oil. Huaxue Shijie (1993), 34(2), 84-7.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Farrington CJ, Chalmers AH: Gas-chromatographic estimation of urinary oxalate and its comparison with a colorimetric method. Clin Chem. 1979 Dec;25(12):1993-6. [PubMed:509698 ]
Lima TM, Kanunfre CC, Pompeia C, Verlengia R, Curi R: Ranking the toxicity of fatty acids on Jurkat and Raji cells by flow cytometric analysis. Toxicol In Vitro. 2002 Dec;16(6):741-7. [PubMed:12423658 ]
Wanten GJ, Janssen FP, Naber AH: Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length. Eur J Clin Invest. 2002 Apr;32(4):285-9. [PubMed:11952815 ]
Lindmark T, Kimura Y, Artursson P: Absorption enhancement through intracellular regulation of tight junction permeability by medium chain fatty acids in Caco-2 cells. J Pharmacol Exp Ther. 1998 Jan;284(1):362-9. [PubMed:9435199 ]
Kaiya H, Van Der Geyten S, Kojima M, Hosoda H, Kitajima Y, Matsumoto M, Geelissen S, Darras VM, Kangawa K: Chicken ghrelin: purification, cDNA cloning, and biological activity. Endocrinology. 2002 Sep;143(9):3454-63. [PubMed:12193558 ]
Eriksson T, Bjorkman S, Roth B, Fyge A, Hoglund P: Enantiomers of thalidomide: blood distribution and the influence of serum albumin on chiral inversion and hydrolysis. Chirality. 1998;10(3):223-8. [PubMed:9499573 ]
Da Silva MA, Medeiros VC, Langone MA, Freire DM: Synthesis of monocaprin catalyzed by lipase. Appl Biochem Biotechnol. 2003 Spring;105 -108:757-67. [PubMed:12721413 ]
Imai T, Sakai M, Ohtake H, Azuma H, Otagiri M: Absorption-enhancing effect of glycyrrhizin induced in the presence of capric acid. Int J Pharm. 2005 Apr 27;294(1-2):11-21. [PubMed:15814227 ]
Leopold CS, Lippold BC: An attempt to clarify the mechanism of the penetration enhancing effects of lipophilic vehicles with differential scanning calorimetry (DSC). J Pharm Pharmacol. 1995 Apr;47(4):276-81. [PubMed:7791023 ]
Saso L, Valentini G, Grippa E, Leone MG, Silvestrini B: Effect of selected substances on heat-induced aggregation of albumin, IgG and lysozyme. Res Commun Mol Pathol Pharmacol. 1998 Oct;102(1):15-28. [PubMed:9920343 ]
Kaiya H, Kojima M, Hosoda H, Riley LG, Hirano T, Grau EG, Kangawa K: Identification of tilapia ghrelin and its effects on growth hormone and prolactin release in the tilapia, Oreochromis mossambicus. Comp Biochem Physiol B Biochem Mol Biol. 2003 Jul;135(3):421-9. [PubMed:12831762 ]
Coyne CB, Ribeiro CM, Boucher RC, Johnson LG: Acute mechanism of medium chain fatty acid-induced enhancement of airway epithelial permeability. J Pharmacol Exp Ther. 2003 May;305(2):440-50. Epub 2003 Feb 11. [PubMed:12606647 ]
Tanaka S, Saitoh O, Tabata K, Matsuse R, Kojima K, Sugi K, Nakagawa K, Kayazawa M, Teranishi T, Uchida K, Hirata I, Katsu K: Medium-chain fatty acids stimulate interleukin-8 production in Caco-2 cells with different mechanisms from long-chain fatty acids. J Gastroenterol Hepatol. 2001 Jul;16(7):748-54. [PubMed:11446882 ]
Duran M, Mitchell G, de Klerk JB, de Jager JP, Hofkamp M, Bruinvis L, Ketting D, Saudubray JM, Wadman SK: Octanoic acidemia and octanoylcarnitine excretion with dicarboxylic aciduria due to defective oxidation of medium-chain fatty acids. J Pediatr. 1985 Sep;107(3):397-404. [PubMed:4032135 ]
Wallon C, Braaf Y, Wolving M, Olaison G, Soderholm JD: Endoscopic biopsies in Ussing chambers evaluated for studies of macromolecular permeability in the human colon. Scand J Gastroenterol. 2005 May;40(5):586-95. [PubMed:16036512 ]
Van Immerseel F, De Buck J, Boyen F, Bohez L, Pasmans F, Volf J, Sevcik M, Rychlik I, Haesebrouck F, Ducatelle R: Medium-chain fatty acids decrease colonization and invasion through hilA suppression shortly after infection of chickens with Salmonella enterica serovar Enteritidis. Appl Environ Microbiol. 2004 Jun;70(6):3582-7. [PubMed:15184160 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Hilditch TP: The component acids of milk fats of the goat, ewe and mare. Biochem J. 1944;38(5):443-7. doi: 10.1042/bj0380443. [PubMed:16747831 ]

Enzymes

Enzyme Details

1. Peroxisomal carnitine O-octanoyltransferase

General function:: Involved in acyltransferase activity
Specific function:: Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate. Converts the end product of pristanic acid beta oxidation, 4,8-dimethylnonanoyl-CoA, to its corresponding carnitine ester.
Gene Name:: CROT
Uniprot ID:: Q9UKG9
Molecular weight:: 10213.63

Enzyme Details

2. Carnitine O-palmitoyltransferase 2, mitochondrial

General function:: Involved in acyltransferase activity
Specific function:: Not Available
Gene Name:: CPT2
Uniprot ID:: P23786
Molecular weight:: 73776.335

Enzyme Details

3. Mitochondrial carnitine/acylcarnitine carrier protein

General function:: Involved in transporter activity
Specific function:: Mediates the transport of acylcarnitines of different length across the mitochondrial inner membrane from the cytosol to the mitochondrial matrix for their oxidation by the mitochondrial fatty acid-oxidation pathway.
Gene Name:: SLC25A20
Uniprot ID:: O43772
Molecular weight:: 32943.46

Enzyme Details

4. Furin

General function:: Involved in serine-type endopeptidase activity
Specific function:: Furin is likely to represent the ubiquitous endoprotease activity within constitutive secretory pathways and capable of cleavage at the RX(K/R)R consensus motif
Gene Name:: FURIN
Uniprot ID:: P09958
Molecular weight:: 86677.4

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

5. Glycolipid transfer protein

General function:: Involved in glycolipid transporter activity
Specific function:: Accelerates the intermembrane transfer of various glycolipids. Catalyzes the transfer of various glycosphingolipids between membranes but does not catalyze the transfer of phospholipids. May be involved in the intracellular translocation of glucosylceramides
Gene Name:: GLTP
Uniprot ID:: Q9NZD2
Molecular weight:: 23849.6

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Showing metabocard for Capric acid (HMDB0000511)

MOL for HMDB0000511 (Capric acid)

3D MOL for HMDB0000511 (Capric acid)

3D SDF for HMDB0000511 (Capric acid)

3D-SDF for HMDB0000511 (Capric acid)

PDB for HMDB0000511 (Capric acid)

3D PDB for HMDB0000511 (Capric acid)

SMILES for HMDB0000511 (Capric acid)

INCHI for HMDB0000511 (Capric acid)

Structure for HMDB0000511 (Capric acid)

3D Structure for HMDB0000511 (Capric acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References