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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-11-30 15:51:17 UTC

Update Date

2020-02-26 21:38:22 UTC

HMDB ID

HMDB0013225

Secondary Accession Numbers

HMDB13225

Metabolite Identification

Common Name

Capryloylcholine

Description

Capryloylcholine is a fatty acid-choline as the ester product of Capryloic acid and cholinel. The pharmacological effects of a series of fatty acid-choline esters have been studied on the isolated rabbit heart, the isolated guinea-pig ileum and the rat stomach. The effect changed with increasing chain length, and three different types of response were observed. The shortchain compounds produced depression of the isolated rabbit heart and spasm of the isolated guinea-pig ileum. Only one, butyrylcholine, had an erratic stimulating effect on hydrochloric acid secretion by the partially vagotomized rat stomach. Medium-chain compounds had a stimulating effect on the isolated rabbit heart, a mixed spasmogenic and relaxant effect on the isolated guinea-pig ileum, and no effect on the rat stomach. Long-chain compounds blocked the effect of acetylcholine on the isolated rabbit heart and the isolated guinea-pig ileum; they also depressed spontaneous hydrochloric acid secretion by the rat stomach.

Structure

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

HMDB0013225
     RDKit          3D
Capryloylcholine
 44 43  0  0  0  0  0  0  0  0999 V2000
    7.5788   -0.1568    0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1059   -0.2127    0.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3526   -0.7690   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8913   -0.9307   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985    0.3097   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -0.1042    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411    1.0690    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570    0.5822    0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916    0.5556    1.6070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3820    0.1554   -0.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7056   -0.3074   -0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6657    0.7336    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0027    0.1701    0.1653 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.6313   -0.1523   -1.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8170    1.1886    0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9568   -0.9716    1.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8335   -1.0904   -0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815    0.6773   -0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2587   -0.1642    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8155    0.8247    0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1034   -0.8684    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816   -0.0864   -1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8357   -1.7341   -0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -1.3599   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876   -1.7190    0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3877    0.8648    0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1661    1.0285   -0.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197   -0.8337    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3265   -0.6496   -0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451    1.5625    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448    1.7629   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0079   -0.6849   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7642   -1.1506    0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802    1.1349    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7448    1.6150   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4325    0.5841   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9019   -0.1721   -1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0913   -1.1706   -0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8620    0.9171    0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5485    1.2195    1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6124    2.1939    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9157   -1.1520    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1379   -0.8465    1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6804   -1.8625    0.4656 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  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
M  CHG  1  13   1
M  END


  Mrv1652307171819202D          

 16 15  0  0  0  0            999 V2000
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5552    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7302    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
M  CHG  1  14   1
M  END
> <DATABASE_ID>
HMDB0013225

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H28NO2/c1-5-6-7-8-9-10-13(15)16-12-11-14(2,3)4/h5-12H2,1-4H3/q+1

> <INCHI_KEY>
AKYPZHWYYXDGEW-UHFFFAOYSA-N

> <FORMULA>
C13H28NO2

> <MOLECULAR_WEIGHT>
230.3669

> <EXACT_MASS>
230.212004145

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
29.078681004955634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trimethyl[2-(octanoyloxy)ethyl]azanium

> <ALOGPS_LOGP>
-1.15

> <JCHEM_LOGP>
-1.2977645804717464

> <ALOGPS_LOGS>
-5.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-7.047174497735868

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
78.9774

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.46e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethyl[2-(octanoyloxy)ethyl]azanium

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0013225
     RDKit          3D
Capryloylcholine
 44 43  0  0  0  0  0  0  0  0999 V2000
    7.5788   -0.1568    0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1059   -0.2127    0.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3526   -0.7690   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8913   -0.9307   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985    0.3097   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -0.1042    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411    1.0690    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570    0.5822    0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916    0.5556    1.6070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3820    0.1554   -0.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7056   -0.3074   -0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6657    0.7336    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0027    0.1701    0.1653 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.6313   -0.1523   -1.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8170    1.1886    0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9568   -0.9716    1.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8335   -1.0904   -0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815    0.6773   -0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2587   -0.1642    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8155    0.8247    0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1034   -0.8684    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816   -0.0864   -1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8357   -1.7341   -0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -1.3599   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876   -1.7190    0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3877    0.8648    0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1661    1.0285   -0.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197   -0.8337    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3265   -0.6496   -0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451    1.5625    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448    1.7629   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0079   -0.6849   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7642   -1.1506    0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802    1.1349    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7448    1.6150   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4325    0.5841   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9019   -0.1721   -1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0913   -1.1706   -0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8620    0.9171    0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5485    1.2195    1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6124    2.1939    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9157   -1.1520    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1379   -0.8465    1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6804   -1.8625    0.4656 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  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
M  CHG  1  13   1
M  END

HEADER    PROTEIN                                 17-JUL-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-18         0                                  
HETATM    1  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.267   5.541   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.703   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.163   6.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.599   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      18.933   4.771   0.000  0.00  0.00           N+1
HETATM   15  O   UNK     0      13.598   6.311   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      14.932   4.001   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   13                                                       
CONECT   11   12   14                                                       
CONECT   12   11   16                                                       
CONECT   13   10   15   16                                                  
CONECT   14    2    3    4   11                                             
CONECT   15   13                                                            
CONECT   16   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0013225
HETATM    1  C1  UNL     1       7.579  -0.157   0.293  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.106  -0.213   0.722  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.353  -0.769  -0.432  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.891  -0.931  -0.268  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.099   0.310  -0.009  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.648  -0.104   0.122  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.741   1.069   0.352  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.657   0.582   0.478  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.192   0.556   1.607  1.00  0.00           O  
HETATM   10  O2  UNL     1      -1.382   0.155  -0.612  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.706  -0.307  -0.466  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.666   0.734   0.041  1.00  0.00           C  
HETATM   13  N1  UNL     1      -5.003   0.170   0.165  1.00  0.00           N1+
HETATM   14  C11 UNL     1      -5.631  -0.152  -1.072  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.817   1.189   0.813  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.957  -0.972   1.063  1.00  0.00           C  
HETATM   17  H1  UNL     1       7.833  -1.090  -0.290  1.00  0.00           H  
HETATM   18  H2  UNL     1       7.782   0.677  -0.402  1.00  0.00           H  
HETATM   19  H3  UNL     1       8.259  -0.164   1.153  1.00  0.00           H  
HETATM   20  H4  UNL     1       5.816   0.825   0.915  1.00  0.00           H  
HETATM   21  H5  UNL     1       6.103  -0.868   1.620  1.00  0.00           H  
HETATM   22  H6  UNL     1       5.582  -0.086  -1.309  1.00  0.00           H  
HETATM   23  H7  UNL     1       5.836  -1.734  -0.719  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.485  -1.360  -1.232  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.688  -1.719   0.483  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.388   0.865   0.894  1.00  0.00           H  
HETATM   27  H11 UNL     1       3.166   1.029  -0.847  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.520  -0.834   0.941  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.327  -0.650  -0.805  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.045   1.563   1.270  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.845   1.763  -0.526  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.008  -0.685  -1.466  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.764  -1.151   0.268  1.00  0.00           H  
HETATM   34  H18 UNL     1      -3.380   1.135   1.033  1.00  0.00           H  
HETATM   35  H19 UNL     1      -3.745   1.615  -0.635  1.00  0.00           H  
HETATM   36  H20 UNL     1      -6.433   0.584  -1.340  1.00  0.00           H  
HETATM   37  H21 UNL     1      -4.902  -0.172  -1.878  1.00  0.00           H  
HETATM   38  H22 UNL     1      -6.091  -1.171  -0.946  1.00  0.00           H  
HETATM   39  H23 UNL     1      -6.862   0.917   0.634  1.00  0.00           H  
HETATM   40  H24 UNL     1      -5.548   1.220   1.890  1.00  0.00           H  
HETATM   41  H25 UNL     1      -5.612   2.194   0.396  1.00  0.00           H  
HETATM   42  H26 UNL     1      -5.916  -1.152   1.567  1.00  0.00           H  
HETATM   43  H27 UNL     1      -4.138  -0.846   1.813  1.00  0.00           H  
HETATM   44  H28 UNL     1      -4.680  -1.863   0.466  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   32   33
CONECT   12   13   34   35
CONECT   13   14   15   16
CONECT   14   36   37   38
CONECT   15   39   40   41
CONECT   16   42   43   44
END

HMDB0013225
     RDKit          3D
Capryloylcholine
 44 43  0  0  0  0  0  0  0  0999 V2000
    7.5788   -0.1568    0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1059   -0.2127    0.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3526   -0.7690   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8913   -0.9307   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985    0.3097   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -0.1042    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411    1.0690    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570    0.5822    0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916    0.5556    1.6070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3820    0.1554   -0.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7056   -0.3074   -0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6657    0.7336    0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0027    0.1701    0.1653 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.6313   -0.1523   -1.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8170    1.1886    0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9568   -0.9716    1.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8335   -1.0904   -0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815    0.6773   -0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2587   -0.1642    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8155    0.8247    0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1034   -0.8684    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816   -0.0864   -1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8357   -1.7341   -0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -1.3599   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876   -1.7190    0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3877    0.8648    0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1661    1.0285   -0.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197   -0.8337    0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3265   -0.6496   -0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451    1.5625    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448    1.7629   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0079   -0.6849   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7642   -1.1506    0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802    1.1349    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7448    1.6150   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4325    0.5841   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9019   -0.1721   -1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0913   -1.1706   -0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8620    0.9171    0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5485    1.2195    1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6124    2.1939    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9157   -1.1520    1.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1379   -0.8465    1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6804   -1.8625    0.4656 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  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
M  CHG  1  13   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₂₈NO₂

Average Molecular Weight

230.3669

Monoisotopic Molecular Weight

230.212004145

IUPAC Name

trimethyl[2-(octanoyloxy)ethyl]azanium

Traditional Name

trimethyl[2-(octanoyloxy)ethyl]azanium

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C13H28NO2/c1-5-6-7-8-9-10-13(15)16-12-11-14(2,3)4/h5-12H2,1-4H3/q+1

InChI Key

AKYPZHWYYXDGEW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Acyl cholines

Alternative Parents

Substituents

Acyl choline
Fatty acid ester
Fatty acyl
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Amine
Organooxygen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0013225)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00045 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.3	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	78.98 m³·mol⁻¹	ChemAxon
Polarizability	29.08 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	162.664	30932474
DeepCCS	[M-H]-	160.302	30932474
DeepCCS	[M-2H]-	194.315	30932474
DeepCCS	[M+Na]+	170.415	30932474
AllCCS	[M+H]+	161.6	32859911
AllCCS	[M+H-H2O]+	158.5	32859911
AllCCS	[M+NH4]+	164.5	32859911
AllCCS	[M+Na]+	165.4	32859911
AllCCS	[M-H]-	168.4	32859911
AllCCS	[M+Na-2H]-	169.7	32859911
AllCCS	[M+HCOO]-	171.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Capryloylcholine	CCCCCCCC(=O)OCC[N+](C)(C)C	1815.5	Standard polar	33892256
Capryloylcholine	CCCCCCCC(=O)OCC[N+](C)(C)C	1326.5	Standard non polar	33892256
Capryloylcholine	CCCCCCCC(=O)OCC[N+](C)(C)C	1558.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Capryloylcholine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029344

KNApSAcK ID

Not Available

Chemspider ID

14582881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22155836

PDB ID

Not Available

ChEBI ID

166482

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Capryloylcholine (HMDB0013225)

MOL for HMDB0013225 (Capryloylcholine)

3D MOL for HMDB0013225 (Capryloylcholine)

3D SDF for HMDB0013225 (Capryloylcholine)

3D-SDF for HMDB0013225 (Capryloylcholine)

PDB for HMDB0013225 (Capryloylcholine)

3D PDB for HMDB0013225 (Capryloylcholine)

SMILES for HMDB0013225 (Capryloylcholine)

INCHI for HMDB0013225 (Capryloylcholine)

Structure for HMDB0013225 (Capryloylcholine)

3D Structure for HMDB0013225 (Capryloylcholine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

NMR Spectra