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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-11-30 15:52:56 UTC

Update Date

2020-02-26 21:38:28 UTC

HMDB ID

HMDB0013322

Secondary Accession Numbers

HMDB13322

Metabolite Identification

Common Name

Undecanoylcholine

Description

Undecanoylcholine is a fatty acid-choline as the ester product of undecanoic 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

HMDB0013322
     RDKit          3D
Undecanoylcholine
 53 52  0  0  0  0  0  0  0  0999 V2000
    4.3937   -3.3191   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2232   -2.0454   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2584   -0.9039   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0410    0.3651   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    1.5813    0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1608    1.8795   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4181    3.1282   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7732    2.9548    0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7921    1.8043    0.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105    2.0377   -0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704    0.9004   -0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.1681   -1.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155    0.5885    0.9455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0528   -0.4611    0.9658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0860   -0.1939   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1171   -1.2068   -0.1601 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.7282   -1.2812    1.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -2.4757   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1032   -0.7441   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9135   -4.0941   -1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3932   -3.1307   -0.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1827   -3.6901    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7450   -1.9160   -1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8902   -2.1115    0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7732   -1.1183    0.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448   -0.8830   -1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8358    0.2586    0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5848    0.4771   -1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7769    1.4554    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992    2.4467    0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    1.1007   -1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    2.0671   -1.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6959    3.3839   -1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1299    3.9947   -0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4659    2.8614    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558    3.8947    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587    0.8763    0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3823    1.6613    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332    2.9963    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0794    2.1880   -1.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5056   -0.4997    1.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4912   -1.4050    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5672    0.7865    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6044   -0.0764   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5208   -0.3781    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8323   -1.3178    1.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3469   -2.1512    1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2483   -3.1429    0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5528   -3.0104   -1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9808   -2.3575   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0759   -1.2636   -0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1941    0.3475   -1.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6865   -1.0266   -2.1259 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  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
M  CHG  1  16   1
M  END


  Mrv1652303102016522D          

 19 18  0  0  0  0            999 V2000
    8.3488   -9.7574    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.4922   -9.3449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0633   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6344  -10.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9363   -9.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7613  -10.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7778   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2067   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9212   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2067  -10.5824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6357   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3502   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0646   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7791   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4936   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2080   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9226   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6370   -9.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3515   -9.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  1  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  2  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
M  CHG  1   1   1
M  END
> <DATABASE_ID>
HMDB0013322

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H34NO2/c1-5-6-7-8-9-10-11-12-13-16(18)19-15-14-17(2,3)4/h5-15H2,1-4H3/q+1

> <INCHI_KEY>
WAKLSXXFSACOOZ-UHFFFAOYSA-N

> <FORMULA>
C16H34NO2

> <MOLECULAR_WEIGHT>
272.4467

> <EXACT_MASS>
272.258954337

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.412921798414985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
0.035941414528254445

> <ALOGPS_LOGS>
-6.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-7.04717449773593

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
92.7804

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.37e-05 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013322
     RDKit          3D
Undecanoylcholine
 53 52  0  0  0  0  0  0  0  0999 V2000
    4.3937   -3.3191   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2232   -2.0454   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2584   -0.9039   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0410    0.3651   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    1.5813    0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1608    1.8795   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4181    3.1282   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7732    2.9548    0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7921    1.8043    0.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105    2.0377   -0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704    0.9004   -0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.1681   -1.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155    0.5885    0.9455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0528   -0.4611    0.9658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0860   -0.1939   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1171   -1.2068   -0.1601 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.7282   -1.2812    1.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -2.4757   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1032   -0.7441   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9135   -4.0941   -1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3932   -3.1307   -0.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1827   -3.6901    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7450   -1.9160   -1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8902   -2.1115    0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7732   -1.1183    0.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448   -0.8830   -1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8358    0.2586    0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5848    0.4771   -1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7769    1.4554    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992    2.4467    0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    1.1007   -1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    2.0671   -1.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6959    3.3839   -1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1299    3.9947   -0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4659    2.8614    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558    3.8947    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587    0.8763    0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3823    1.6613    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332    2.9963    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0794    2.1880   -1.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5056   -0.4997    1.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4912   -1.4050    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5672    0.7865    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6044   -0.0764   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5208   -0.3781    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8323   -1.3178    1.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3469   -2.1512    1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2483   -3.1429    0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5528   -3.0104   -1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9808   -2.3575   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0759   -1.2636   -0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1941    0.3475   -1.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6865   -1.0266   -2.1259 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  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
M  CHG  1  16   1
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  N   UNK     0      15.584 -18.214   0.000  0.00  0.00           N+1
HETATM    2  O   UNK     0      19.585 -17.444   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      16.918 -17.444   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.251 -18.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.814 -16.880   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.354 -19.547   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.252 -18.214   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.919 -18.214   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.253 -17.444   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      20.919 -19.754   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      23.587 -18.214   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.920 -17.444   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.254 -18.214   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.588 -17.444   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.921 -18.214   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.255 -17.444   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.589 -18.214   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.922 -17.444   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.256 -18.214   0.000  0.00  0.00           C+0
CONECT    1    3    4    5    6                                             
CONECT    2    7    8                                                       
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    2    3                                                       
CONECT    8    2    9   10                                                  
CONECT    9    8   11                                                       
CONECT   10    8                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0013322
HETATM    1  C1  UNL     1       4.394  -3.319  -0.477  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.223  -2.045  -0.418  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.258  -0.904  -0.142  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.041   0.365  -0.070  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.206   1.581   0.205  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.161   1.879  -0.812  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.418   3.128  -0.370  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.773   2.955   0.965  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.792   1.804   0.930  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.311   2.038  -0.049  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.270   0.900  -0.097  1.00  0.00           C  
HETATM   12  O1  UNL     1      -1.337   0.168  -1.126  1.00  0.00           O  
HETATM   13  O2  UNL     1      -2.116   0.589   0.945  1.00  0.00           O  
HETATM   14  C12 UNL     1      -3.053  -0.461   0.966  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.086  -0.194  -0.076  1.00  0.00           C  
HETATM   16  N1  UNL     1      -5.117  -1.207  -0.160  1.00  0.00           N1+
HETATM   17  C14 UNL     1      -5.728  -1.281   1.149  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.639  -2.476  -0.633  1.00  0.00           C  
HETATM   19  C16 UNL     1      -6.103  -0.744  -1.119  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.913  -4.094  -1.065  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.393  -3.131  -0.926  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.183  -3.690   0.565  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.745  -1.916  -1.375  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.890  -2.111   0.458  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.773  -1.118   0.822  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.545  -0.883  -1.004  1.00  0.00           H  
HETATM   27  H8  UNL     1       5.836   0.259   0.693  1.00  0.00           H  
HETATM   28  H9  UNL     1       5.585   0.477  -1.051  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.777   1.455   1.226  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.899   2.447   0.248  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.435   1.101  -1.019  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.692   2.067  -1.788  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.696   3.384  -1.145  1.00  0.00           H  
HETATM   34  H15 UNL     1       3.130   3.995  -0.281  1.00  0.00           H  
HETATM   35  H16 UNL     1       2.466   2.861   1.814  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.156   3.895   1.140  1.00  0.00           H  
HETATM   37  H18 UNL     1       1.359   0.876   0.667  1.00  0.00           H  
HETATM   38  H19 UNL     1       0.382   1.661   1.964  1.00  0.00           H  
HETATM   39  H20 UNL     1      -0.833   2.996   0.238  1.00  0.00           H  
HETATM   40  H21 UNL     1       0.079   2.188  -1.056  1.00  0.00           H  
HETATM   41  H22 UNL     1      -3.506  -0.500   1.984  1.00  0.00           H  
HETATM   42  H23 UNL     1      -2.491  -1.405   0.777  1.00  0.00           H  
HETATM   43  H24 UNL     1      -4.567   0.786   0.187  1.00  0.00           H  
HETATM   44  H25 UNL     1      -3.604  -0.076  -1.061  1.00  0.00           H  
HETATM   45  H26 UNL     1      -5.521  -0.378   1.750  1.00  0.00           H  
HETATM   46  H27 UNL     1      -6.832  -1.318   1.015  1.00  0.00           H  
HETATM   47  H28 UNL     1      -5.347  -2.151   1.737  1.00  0.00           H  
HETATM   48  H29 UNL     1      -4.248  -3.143   0.159  1.00  0.00           H  
HETATM   49  H30 UNL     1      -5.553  -3.010  -1.028  1.00  0.00           H  
HETATM   50  H31 UNL     1      -3.981  -2.358  -1.495  1.00  0.00           H  
HETATM   51  H32 UNL     1      -7.076  -1.264  -0.993  1.00  0.00           H  
HETATM   52  H33 UNL     1      -6.194   0.348  -1.113  1.00  0.00           H  
HETATM   53  H34 UNL     1      -5.687  -1.027  -2.126  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10   37   38
CONECT   10   11   39   40
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   41   42
CONECT   15   16   43   44
CONECT   16   17   18   19
CONECT   17   45   46   47
CONECT   18   48   49   50
CONECT   19   51   52   53
END

HMDB0013322
     RDKit          3D
Undecanoylcholine
 53 52  0  0  0  0  0  0  0  0999 V2000
    4.3937   -3.3191   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2232   -2.0454   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2584   -0.9039   -0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0410    0.3651   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    1.5813    0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1608    1.8795   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4181    3.1282   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7732    2.9548    0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7921    1.8043    0.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105    2.0377   -0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704    0.9004   -0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.1681   -1.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155    0.5885    0.9455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0528   -0.4611    0.9658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0860   -0.1939   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1171   -1.2068   -0.1601 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.7282   -1.2812    1.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6394   -2.4757   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1032   -0.7441   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9135   -4.0941   -1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3932   -3.1307   -0.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1827   -3.6901    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7450   -1.9160   -1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8902   -2.1115    0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7732   -1.1183    0.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448   -0.8830   -1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8358    0.2586    0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5848    0.4771   -1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7769    1.4554    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992    2.4467    0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    1.1007   -1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917    2.0671   -1.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6959    3.3839   -1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1299    3.9947   -0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4659    2.8614    1.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558    3.8947    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3587    0.8763    0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3823    1.6613    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332    2.9963    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0794    2.1880   -1.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5056   -0.4997    1.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4912   -1.4050    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5672    0.7865    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6044   -0.0764   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5208   -0.3781    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8323   -1.3178    1.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3469   -2.1512    1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2483   -3.1429    0.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5528   -3.0104   -1.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9808   -2.3575   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0759   -1.2636   -0.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1941    0.3475   -1.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6865   -1.0266   -2.1259 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  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
M  CHG  1  16   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Undecanoyl choline	HMDB

Chemical Formula

C₁₆H₃₄NO₂

Average Molecular Weight

272.4467

Monoisotopic Molecular Weight

272.258954337

IUPAC Name

trimethyl[2-(undecanoyloxy)ethyl]azanium

Traditional Name

trimethyl[2-(undecanoyloxy)ethyl]azanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H34NO2/c1-5-6-7-8-9-10-11-12-13-16(18)19-15-14-17(2,3)4/h5-15H2,1-4H3/q+1

InChI Key

WAKLSXXFSACOOZ-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: HMDB0013322)

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	5.4e-05 g/L	ALOGPS
logP	0.43	ALOGPS
logP	0.036	ChemAxon
logS	-6.8	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	13	ChemAxon
Refractivity	92.78 m³·mol⁻¹	ChemAxon
Polarizability	35.41 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	179.62	30932474
DeepCCS	[M-H]-	177.261	30932474
DeepCCS	[M-2H]-	210.285	30932474
DeepCCS	[M+Na]+	186.914	30932474
AllCCS	[M+H]+	177.5	32859911
AllCCS	[M+H-H2O]+	174.7	32859911
AllCCS	[M+NH4]+	180.1	32859911
AllCCS	[M+Na]+	180.8	32859911
AllCCS	[M-H]-	180.7	32859911
AllCCS	[M+Na-2H]-	182.0	32859911
AllCCS	[M+HCOO]-	183.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.54 minutes	32390414
Predicted by Siyang on May 30, 2022	15.7629 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.08 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2112.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	244.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	203.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	669.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	652.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	514.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1766.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	436.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1814.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	409.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	259.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	162.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Undecanoylcholine	CCCCCCCCCCC(=O)OCC[N+](C)(C)C	2111.1	Standard polar	33892256
Undecanoylcholine	CCCCCCCCCCC(=O)OCC[N+](C)(C)C	1636.1	Standard non polar	33892256
Undecanoylcholine	CCCCCCCCCCC(=O)OCC[N+](C)(C)C	1871.5	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 - Undecanoylcholine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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

FDB029383

KNApSAcK ID

Not Available

Chemspider ID

30776707

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481666

PDB ID

Not Available

ChEBI ID

Not Available

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 Undecanoylcholine (HMDB0013322)

MOL for HMDB0013322 (Undecanoylcholine)

3D MOL for HMDB0013322 (Undecanoylcholine)

3D SDF for HMDB0013322 (Undecanoylcholine)

3D-SDF for HMDB0013322 (Undecanoylcholine)

PDB for HMDB0013322 (Undecanoylcholine)

3D PDB for HMDB0013322 (Undecanoylcholine)

SMILES for HMDB0013322 (Undecanoylcholine)

INCHI for HMDB0013322 (Undecanoylcholine)

Structure for HMDB0013322 (Undecanoylcholine)

3D Structure for HMDB0013322 (Undecanoylcholine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra