NP-MRD: Showing NP-Card for Capric acid (NP0000313)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2022-02-10 02:10:52 UTC

NP-MRD ID

NP0000313

Secondary Accession Numbers

None

Natural Product 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 NMR Assignments

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 Mass

172.2646 Da

Monoisotopic Mass

172.14633 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-02-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, experimental)	Ahselim			2022-02-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agave decipiens	LOTUS Database	35616633
Ailuropoda melanoleuca	LOTUS Database	35616633
Alpinia latilabris	LOTUS Database	35616633
Anthemis aciphylla	LOTUS Database	35616633
Anthemis aciphylla BOISS.var.discoidea BOISS	Plant	KNApSAcK
Anthemis tinctoria	LOTUS Database	35616633
Arabidopsis thaliana	Plant	KNApSAcK
Arnica montana	LOTUS Database	35616633
Artemisia xerophytica	LOTUS Database	35616633
Attalea colenda	LOTUS Database	35616633
Attalea speciosa	LOTUS Database	35616633
Bellis perennis	LOTUS Database	35616633
Canarium album	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Chlamydomonas reinhardtii	LOTUS Database	35616633
Cinnamomum triplinerve	LOTUS Database	35616633
Cistus creticus	Plant	KNApSAcK
Citropsis articulata	LOTUS Database	35616633
Citrus aurantiifolia	LOTUS Database	35616633
Clinopodium gilliesii	LOTUS Database	35616633
Cocos nucifera	Plant	KNApSAcK
Coriandrum sativum	LOTUS Database	35616633
Cuphea koehneana	Plant	KNApSAcK
Cuphea spp.	Plant	KNApSAcK
Cyperus conglomeratus	LOTUS Database	35616633
Daphne papyracea	LOTUS Database	35616633
Dictamnus albus	LOTUS Database	35616633
Dipteryx lacunifera	LOTUS Database	35616633
Drymaria cordata	Plant	KNApSAcK
Duhaldea cappa	LOTUS Database	35616633
Elaeagnus angustifolia	LOTUS Database	35616633
Erigeron philadelphicus	LOTUS Database	35616633
Erucaria microcarpa	LOTUS Database	35616633
Eryngium foetidum	LOTUS Database	35616633
Etlingera elatior	LOTUS Database	35616633
Fagopyrum esculentum	LOTUS Database	35616633
Festuca rubra	LOTUS Database	35616633
Geum heterocarpum	LOTUS Database	35616633
Glycyrrhiza glabra	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Helichrysum stoechas	LOTUS Database	35616633
Homo sapiens (Serum)	Animalia	KNApSAcK
Houttuynia cordata	Plant	KNApSAcK
Houttuynia emeiensis	Plant	KNApSAcK
Hypericum maculatum	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Isatis tinctoria	LOTUS Database	35616633
Lepidium meyenii	LOTUS Database	35616633
Lindera neesiana	LOTUS Database	35616633
Litsea glutinosa	LOTUS Database	35616633
Litsea monopetala	Plant	KNApSAcK
Lonicera japonica	LOTUS Database	35616633
Lumbricus terrestris	LOTUS Database	35616633
Malva sylvestris	LOTUS Database	35616633
Mandragora autumnalis	LOTUS Database	35616633
Mentha spicata	LOTUS Database	35616633
Momordica charantia	LOTUS Database	35616633
Narthecium ossifragum	LOTUS Database	35616633
Necrodes surinamensis	LOTUS Database	35616633
Notopterygium franchetii	LOTUS Database	35616633
Nymphaea alba	Plant	KNApSAcK
Oecophylla smaragdina	LOTUS Database	35616633
Origanum vulgare	LOTUS Database	35616633
Pelargonium graveolens	LOTUS Database	35616633
Phaseolus coccineus	LOTUS Database	35616633
Pinus radiata	LOTUS Database	35616633
Pinus sibirica	Plant	KNApSAcK
Plumeria rubra	LOTUS Database	35616633
Portulaca oleracea	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633
Punica granatum	Plant	KNApSAcK
Pycnandra acuminata	LOTUS Database	35616633
Rhodiola rosea	Plant	KNApSAcK
Rhododendron sichotense	LOTUS Database	35616633
Ruellia tuberosa	LOTUS Database	35616633
Salmonella enterica	LOTUS Database	35616633
Salvadora oleoides	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Saussurea involucrata	LOTUS Database	35616633
Saxifraga stolonifera	LOTUS Database	35616633
Saxifraga stolonifera Meerb.	Plant	KNApSAcK
Scutellaria baicalensis	LOTUS Database	35616633
Sebertia acuminata	Plant	KNApSAcK
Senecio adenotrichius	LOTUS Database	35616633
Serenoa repens	LOTUS Database	35616633
Sideritis taurica	LOTUS Database	35616633
Sinapis alba	Plant	KNApSAcK
Solanum pennellii	LOTUS Database	35616633
Syagrus romanzoffiana	LOTUS Database	35616633
Tanacetum macrophyllum	Plant	KNApSAcK
Tilia platyphyllos	LOTUS Database	35616633
Tordylium apulum	LOTUS Database	35616633
Trigonella foenum-graecum	LOTUS Database	35616633
Tripleurospermum maritimum	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Xerula pudens	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	31.9 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.062 mg/mL	Not Available
LogP	4.09	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted 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

External Links

HMDB ID

HMDB0000511

DrugBank ID

DB03600

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1007741

References

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 ]
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 ]
Andersen JV, Westi EW, Jakobsen E, Urruticoechea N, Borges K, Aldana BI: Astrocyte metabolism of the medium-chain fatty acids octanoic acid and decanoic acid promotes GABA synthesis in neurons via elevated glutamine supply. Mol Brain. 2021 Sep 3;14(1):132. doi: 10.1186/s13041-021-00842-2. [PubMed:34479615 ]

Showing NP-Card for Capric acid (NP0000313)

MOL for NP0000313 (Capric acid)

3D MOL for NP0000313 (Capric acid)

3D SDF for NP0000313 (Capric acid)

3D-SDF for NP0000313 (Capric acid)

PDB for NP0000313 (Capric acid)

3D PDB for NP0000313 (Capric acid)

SMILES for NP0000313 (Capric acid)

INCHI for NP0000313 (Capric acid)

Structure for NP0000313 (Capric acid)

3D Structure for NP0000313 (Capric acid)