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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-11-30 15:51:04 UTC

Update Date

2020-02-26 21:38:21 UTC

HMDB ID

HMDB0013213

Secondary Accession Numbers

HMDB13213

Metabolite Identification

Common Name

Alpha-Linoleoylcholine

Description

alpha-Linoleoylcholine is a fatty acid-choline as the ester product of alpha-Linoleoic 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


  Mrv1652303102016502D          

 26 25  0  0  0  0            999 V2000
    8.7836  -10.4990    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.2126  -12.1490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4981  -10.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0691  -10.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1961   -9.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3711  -11.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4981  -11.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678  -14.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678  -15.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7823  -15.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7823  -16.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4968  -17.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4968  -17.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2113  -18.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9257  -17.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6402  -18.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547  -17.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547  -17.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0691  -16.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0691  -15.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7836  -15.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7836  -14.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4981  -14.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4981  -13.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2126  -12.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9270  -13.3865    0.0000 O   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  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  2 25  1  0  0  0  0
M  CHG  1   1   1
M  END

HMDB0013213
     RDKit          3D
Alpha-Linoleoylcholine
 70 69  0  0  0  0  0  0  0  0999 V2000
   -9.2558    0.5339    2.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9786    0.9714    2.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8208    0.0589    2.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6394    0.1147    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4924   -0.7725    0.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3704   -0.6748   -0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3050   -0.2423   -1.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1018    0.1981   -0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7575    1.6022   -0.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350    1.9837   -1.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619    1.0317   -1.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    1.1921   -3.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271    0.3510   -4.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0557    0.3839   -3.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -0.0143   -2.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283   -1.4224   -1.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365   -1.8676   -0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9833   -1.8963   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7879   -1.6283   -1.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5214   -2.2175    0.8814 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9118   -2.2410    1.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6018   -0.9374    0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1243    0.1202    1.7235 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.2128    0.9841    2.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2327    0.9512    0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902   -0.3282    2.8783 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1149    0.9759    2.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2667    0.9180    1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3043   -0.5687    2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7290    1.9858    2.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1086    1.0354    4.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9326    0.4695    3.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0731   -0.9684    2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5986   -0.1968    0.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4675    1.1735    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9106   -1.8271    0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288   -0.7279    1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2250   -0.9826   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2231   -0.1732   -2.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858    0.1467    0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3193   -0.5476   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194    2.3792   -0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3919    3.0449   -1.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6606    0.0123   -1.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3459    1.4245   -1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0780    2.2896   -3.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3690    1.0659   -3.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2320   -0.7180   -4.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    0.6456   -5.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4112    1.4612   -3.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6759   -0.1653   -4.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6697   -0.0850   -2.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125    0.7272   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0311   -1.5474   -2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5835   -2.1335   -2.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0405   -2.8377   -0.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853   -1.1393    0.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0724   -2.6645    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3202   -3.0197    0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5558   -0.6449   -0.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6791   -1.0775    1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2854    1.8883    1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0786    1.3335    3.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1970    0.4718    2.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4418    0.8087   -0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3097    2.0300    1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1996    0.5907    1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8626   -1.1346    3.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3353   -0.5069    2.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3536    0.5538    3.5824 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
M  CHG  1  23   1
M  END


  Mrv1652303102016502D          

 26 25  0  0  0  0            999 V2000
    8.7836  -10.4990    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.2126  -12.1490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4981  -10.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0691  -10.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1961   -9.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3711  -11.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4981  -11.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678  -14.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678  -15.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7823  -15.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7823  -16.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4968  -17.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4968  -17.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2113  -18.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9257  -17.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6402  -18.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547  -17.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547  -17.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0691  -16.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0691  -15.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7836  -15.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7836  -14.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4981  -14.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4981  -13.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2126  -12.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9270  -13.3865    0.0000 O   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  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  2 25  1  0  0  0  0
M  CHG  1   1   1
M  END
> <DATABASE_ID>
HMDB0013213

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H44NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(25)26-22-21-24(2,3)4/h9-10,12-13H,5-8,11,14-22H2,1-4H3/q+1/b10-9-,13-12-

> <INCHI_KEY>
FDCFEKFQGUEBOI-UTJQPWESSA-N

> <FORMULA>
C23H44NO2

> <MOLECULAR_WEIGHT>
366.601

> <EXACT_MASS>
366.337204657

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
47.53684211469949

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
trimethyl({2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]ethyl})azanium

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
2.4240787561949215

> <ALOGPS_LOGS>
-7.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-7.047174497735996

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
127.22059999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethyl({2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]ethyl})azanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013213
     RDKit          3D
Alpha-Linoleoylcholine
 70 69  0  0  0  0  0  0  0  0999 V2000
   -9.2558    0.5339    2.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9786    0.9714    2.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8208    0.0589    2.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6394    0.1147    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4924   -0.7725    0.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3704   -0.6748   -0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3050   -0.2423   -1.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1018    0.1981   -0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7575    1.6022   -0.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6350    1.9837   -1.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619    1.0317   -1.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    1.1921   -3.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271    0.3510   -4.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0557    0.3839   -3.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -0.0143   -2.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283   -1.4224   -1.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365   -1.8676   -0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9833   -1.8963   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7879   -1.6283   -1.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5214   -2.2175    0.8814 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9118   -2.2410    1.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6018   -0.9374    0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1243    0.1202    1.7235 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.2128    0.9841    2.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2327    0.9512    0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3902   -0.3282    2.8783 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1149    0.9759    2.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2667    0.9180    1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3043   -0.5687    2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7290    1.9858    2.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1086    1.0354    4.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9326    0.4695    3.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0731   -0.9684    2.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5986   -0.1968    0.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4675    1.1735    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9106   -1.8271    0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6288   -0.7279    1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2250   -0.9826   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2231   -0.1732   -2.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858    0.1467    0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3193   -0.5476   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194    2.3792   -0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3919    3.0449   -1.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6606    0.0123   -1.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3459    1.4245   -1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0780    2.2896   -3.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3690    1.0659   -3.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2320   -0.7180   -4.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    0.6456   -5.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4112    1.4612   -3.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6759   -0.1653   -4.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6697   -0.0850   -2.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125    0.7272   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0311   -1.5474   -2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5835   -2.1335   -2.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0405   -2.8377   -0.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853   -1.1393    0.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0724   -2.6645    2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3202   -3.0197    0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5558   -0.6449   -0.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6791   -1.0775    1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2854    1.8883    1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0786    1.3335    3.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1970    0.4718    2.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4418    0.8087   -0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3097    2.0300    1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1996    0.5907    1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8626   -1.1346    3.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3353   -0.5069    2.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3536    0.5538    3.5824 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  0
 17 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
M  CHG  1  23   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      16.396 -19.598   0.000  0.00  0.00           N+1
HETATM    2  O   UNK     0      19.064 -22.678   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      17.730 -20.368   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.062 -18.828   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.166 -18.264   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.626 -20.932   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.730 -21.908   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.727 -27.298   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.727 -28.838   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.060 -29.608   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.060 -31.148   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.394 -31.918   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.394 -33.458   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.728 -34.228   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.061 -33.458   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.395 -34.228   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.729 -33.458   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.729 -31.918   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.062 -31.148   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.062 -29.608   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.396 -28.838   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.396 -27.298   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.730 -26.528   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.730 -24.988   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.064 -24.218   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      20.397 -24.988   0.000  0.00  0.00           O+0
CONECT    1    3    4    5    6                                             
CONECT    2    7   25                                                       
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    2    3                                                       
CONECT    8    9                                                            
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   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   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26    2                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0013213
HETATM    1  C1  UNL     1      -9.256   0.534   2.263  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.979   0.971   2.944  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.821   0.059   2.596  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.639   0.115   1.102  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.492  -0.773   0.641  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.370  -0.675  -0.800  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.305  -0.242  -1.408  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.102   0.198  -0.676  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.758   1.602  -0.960  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.635   1.984  -1.477  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.562   1.032  -1.842  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.349   1.192  -3.322  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.627   0.351  -4.009  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.056   0.384  -3.676  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.515  -0.014  -2.322  1.00  0.00           C  
HETATM   16  C16 UNL     1       2.128  -1.422  -1.955  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.537  -1.868  -0.607  1.00  0.00           C  
HETATM   18  C18 UNL     1       3.983  -1.896  -0.366  1.00  0.00           C  
HETATM   19  O1  UNL     1       4.788  -1.628  -1.290  1.00  0.00           O  
HETATM   20  O2  UNL     1       4.521  -2.217   0.881  1.00  0.00           O  
HETATM   21  C19 UNL     1       5.912  -2.241   1.103  1.00  0.00           C  
HETATM   22  C20 UNL     1       6.602  -0.937   0.879  1.00  0.00           C  
HETATM   23  N1  UNL     1       6.124   0.120   1.723  1.00  0.00           N1+
HETATM   24  C21 UNL     1       7.213   0.984   2.148  1.00  0.00           C  
HETATM   25  C22 UNL     1       5.233   0.951   0.931  1.00  0.00           C  
HETATM   26  C23 UNL     1       5.390  -0.328   2.878  1.00  0.00           C  
HETATM   27  H1  UNL     1     -10.115   0.976   2.806  1.00  0.00           H  
HETATM   28  H2  UNL     1      -9.267   0.918   1.208  1.00  0.00           H  
HETATM   29  H3  UNL     1      -9.304  -0.569   2.269  1.00  0.00           H  
HETATM   30  H4  UNL     1      -7.729   1.986   2.574  1.00  0.00           H  
HETATM   31  H5  UNL     1      -8.109   1.035   4.048  1.00  0.00           H  
HETATM   32  H6  UNL     1      -5.933   0.470   3.121  1.00  0.00           H  
HETATM   33  H7  UNL     1      -7.073  -0.968   2.944  1.00  0.00           H  
HETATM   34  H8  UNL     1      -7.599  -0.197   0.643  1.00  0.00           H  
HETATM   35  H9  UNL     1      -6.468   1.173   0.821  1.00  0.00           H  
HETATM   36  H10 UNL     1      -5.911  -1.827   0.839  1.00  0.00           H  
HETATM   37  H11 UNL     1      -4.629  -0.728   1.272  1.00  0.00           H  
HETATM   38  H12 UNL     1      -6.225  -0.983  -1.452  1.00  0.00           H  
HETATM   39  H13 UNL     1      -4.223  -0.173  -2.507  1.00  0.00           H  
HETATM   40  H14 UNL     1      -3.186   0.147   0.434  1.00  0.00           H  
HETATM   41  H15 UNL     1      -2.319  -0.548  -0.914  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.519   2.379  -0.710  1.00  0.00           H  
HETATM   43  H17 UNL     1      -1.392   3.045  -1.685  1.00  0.00           H  
HETATM   44  H18 UNL     1      -0.661   0.012  -1.532  1.00  0.00           H  
HETATM   45  H19 UNL     1       0.346   1.425  -1.269  1.00  0.00           H  
HETATM   46  H20 UNL     1      -0.078   2.290  -3.515  1.00  0.00           H  
HETATM   47  H21 UNL     1      -1.369   1.066  -3.787  1.00  0.00           H  
HETATM   48  H22 UNL     1       0.232  -0.718  -4.072  1.00  0.00           H  
HETATM   49  H23 UNL     1       0.567   0.646  -5.122  1.00  0.00           H  
HETATM   50  H24 UNL     1       2.411   1.461  -3.813  1.00  0.00           H  
HETATM   51  H25 UNL     1       2.676  -0.165  -4.446  1.00  0.00           H  
HETATM   52  H26 UNL     1       3.670  -0.085  -2.441  1.00  0.00           H  
HETATM   53  H27 UNL     1       2.413   0.727  -1.537  1.00  0.00           H  
HETATM   54  H28 UNL     1       1.031  -1.547  -2.101  1.00  0.00           H  
HETATM   55  H29 UNL     1       2.583  -2.134  -2.705  1.00  0.00           H  
HETATM   56  H30 UNL     1       2.041  -2.838  -0.373  1.00  0.00           H  
HETATM   57  H31 UNL     1       2.085  -1.139   0.139  1.00  0.00           H  
HETATM   58  H32 UNL     1       6.072  -2.664   2.110  1.00  0.00           H  
HETATM   59  H33 UNL     1       6.320  -3.020   0.397  1.00  0.00           H  
HETATM   60  H34 UNL     1       6.556  -0.645  -0.169  1.00  0.00           H  
HETATM   61  H35 UNL     1       7.679  -1.077   1.115  1.00  0.00           H  
HETATM   62  H36 UNL     1       7.285   1.888   1.509  1.00  0.00           H  
HETATM   63  H37 UNL     1       7.079   1.333   3.197  1.00  0.00           H  
HETATM   64  H38 UNL     1       8.197   0.472   2.075  1.00  0.00           H  
HETATM   65  H39 UNL     1       5.442   0.809  -0.143  1.00  0.00           H  
HETATM   66  H40 UNL     1       5.310   2.030   1.230  1.00  0.00           H  
HETATM   67  H41 UNL     1       4.200   0.591   1.106  1.00  0.00           H  
HETATM   68  H42 UNL     1       5.863  -1.135   3.439  1.00  0.00           H  
HETATM   69  H43 UNL     1       4.335  -0.507   2.596  1.00  0.00           H  
HETATM   70  H44 UNL     1       5.354   0.554   3.582  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7    7   38
CONECT    7    8   39
CONECT    8    9   40   41
CONECT    9   10   10   42
CONECT   10   11   43
CONECT   11   12   44   45
CONECT   12   13   46   47
CONECT   13   14   48   49
CONECT   14   15   50   51
CONECT   15   16   52   53
CONECT   16   17   54   55
CONECT   17   18   56   57
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   58   59
CONECT   22   23   60   61
CONECT   23   24   25   26
CONECT   24   62   63   64
CONECT   25   65   66   67
CONECT   26   68   69   70
END

HMDB0013213
     RDKit          3D
Alpha-Linoleoylcholine
 70 69  0  0  0  0  0  0  0  0999 V2000
   -9.2558    0.5339    2.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9786    0.9714    2.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8208    0.0589    2.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
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 26 70  1  0
M  CHG  1  23   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Linoleoylcholine	Generator
Α-linoleoylcholine	Generator

Chemical Formula

C₂₃H₄₄NO₂

Average Molecular Weight

366.601

Monoisotopic Molecular Weight

366.337204657

IUPAC Name

trimethyl({2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]ethyl})azanium

Traditional Name

trimethyl({2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]ethyl})azanium

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C23H44NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(25)26-22-21-24(2,3)4/h9-10,12-13H,5-8,11,14-22H2,1-4H3/q+1/b10-9-,13-12-

InChI Key

FDCFEKFQGUEBOI-UTJQPWESSA-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

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0013213)

Cellular substructure

Membrane (HMDB: HMDB0013213)

Source

Endogenous

Endogenous (HMDB: HMDB0013213)

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	1.0e-05 g/L	ALOGPS
logP	3.08	ALOGPS
logP	2.42	ChemAxon
logS	-7.6	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	18	ChemAxon
Refractivity	127.22 m³·mol⁻¹	ChemAxon
Polarizability	47.54 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]+	206.35	30932474
DeepCCS	[M-H]-	202.406	30932474
DeepCCS	[M-2H]-	238.874	30932474
DeepCCS	[M+Na]+	215.165	30932474
AllCCS	[M+H]+	205.8	32859911
AllCCS	[M+H-H2O]+	203.6	32859911
AllCCS	[M+NH4]+	207.8	32859911
AllCCS	[M+Na]+	208.4	32859911
AllCCS	[M-H]-	201.7	32859911
AllCCS	[M+Na-2H]-	204.0	32859911
AllCCS	[M+HCOO]-	206.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alpha-Linoleoylcholine	CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C	2905.9	Standard polar	33892256
Alpha-Linoleoylcholine	CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C	2280.6	Standard non polar	33892256
Alpha-Linoleoylcholine	CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C	2509.0	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 - Alpha-Linoleoylcholine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

FDB029337

KNApSAcK ID

Not Available

Chemspider ID

30776702

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481656

PDB ID

Not Available

ChEBI ID

166485

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 Alpha-Linoleoylcholine (HMDB0013213)

MOL for HMDB0013213 (Alpha-Linoleoylcholine)

3D MOL for HMDB0013213 (Alpha-Linoleoylcholine)

3D SDF for HMDB0013213 (Alpha-Linoleoylcholine)

3D-SDF for HMDB0013213 (Alpha-Linoleoylcholine)

PDB for HMDB0013213 (Alpha-Linoleoylcholine)

3D PDB for HMDB0013213 (Alpha-Linoleoylcholine)

SMILES for HMDB0013213 (Alpha-Linoleoylcholine)

INCHI for HMDB0013213 (Alpha-Linoleoylcholine)

Structure for HMDB0013213 (Alpha-Linoleoylcholine)

3D Structure for HMDB0013213 (Alpha-Linoleoylcholine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra