Hmdb loader

Showing metabocard for 9-Hexadecenoylcholine (HMDB0013208)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-11-30 15:50:59 UTC
Update Date2020-02-26 21:38:20 UTC
HMDB IDHMDB0013208
Secondary Accession Numbers
  • HMDB13208
Metabolite Identification
Common Name9-Hexadecenoylcholine
Description9-Hexadecenoylcholine, also known as palmitoloelycholine, is a fatty acid-choline and is the ester product of 9-hexadecenoic acid and choline. 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 short-chain 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
Data?1582753100
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013208 (9-Hexadecenoylcholine)


  Mrv1652303062020272D          

 24 23  0  0  0  0            999 V2000
 9997.661710000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.376810000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.091710000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.806510000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.521410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.236510000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.952210000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.665710000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.381410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.206410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.922110000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.635710000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.351410000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.067110000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.780810000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.496410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.944910000.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.230010000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.515110000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.800310000.9868    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9994.083110000.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.800310001.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.948110001.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.661710001.8113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  1  0  0  0  0
  1 24  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  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
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
M  CHG  1  20   1
M  END
Download

3D MOL for HMDB0013208 (9-Hexadecenoylcholine)

HMDB0013208
     RDKit          3D
9-Hexadecenoylcholine
 66 65  0  0  0  0  0  0  0  0999 V2000
   -9.9211    2.2149    0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8677    1.7327   -0.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5957    0.3047   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5792   -0.3496   -1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2261    0.3018   -1.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6404    0.2843    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4754   -1.0875    0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2949   -1.5622    1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0156   -0.8439    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056   -1.5016    0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -0.6727    0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1106   -0.5435    1.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    0.2328    1.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868   -0.1227    1.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -0.2694   -0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0543   -0.5537   -0.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516   -1.6725   -0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369    0.4956   -0.9891 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2168    0.4612   -1.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9906    0.0442   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3968    0.0250   -0.2790 N   0  0  0  0  0  4  0  0  0  0  0  0
    8.6986   -0.1174   -1.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0433   -1.0776    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0623    1.2422    0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5117    1.3773    0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6249    2.9325   -0.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4379    2.7197    1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3309    1.8476   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9799    2.3810   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5597   -0.2582   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3278    0.1588    0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4552   -1.4047   -0.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9175   -0.3655   -2.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5478   -0.3193   -1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861    1.3205   -1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3959    0.7839    0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7580    0.9332    0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3936   -1.7062    0.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3180   -2.6073    1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    0.2140    0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5849   -0.9437    2.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628   -2.4998    0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3366   -1.5774   -0.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1134   -1.0901   -0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0671    0.3378   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8870    0.0401    2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0831   -1.5172    2.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    0.4024    2.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841    1.3347    1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421   -1.0295    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462    0.6808    1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0225   -1.1129   -0.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3529    0.6320   -1.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5303    1.5150   -1.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4891   -0.1876   -2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6748   -0.9197    0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7954    0.8175    0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    0.7079   -2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8215   -0.0816   -1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3954   -1.1099   -2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1388   -0.8212    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7023   -1.1494    1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8934   -1.9851   -0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1067    0.9957    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0655    1.9425   -0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5592    1.6459    1.0769 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  2  0
  8  9  1  0
  9 10  1  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  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 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
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 24 66  1  0
M  CHG  1  21   1
M  END
Download

3D SDF for HMDB0013208 (9-Hexadecenoylcholine)


  Mrv1652303062020272D          

 24 23  0  0  0  0            999 V2000
 9997.661710000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.376810000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.091710000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.806510000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.521410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.236510000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.952210000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.665710000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.381410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.206410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.922110000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.635710000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.351410000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.067110000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.780810000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.496410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.944910000.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.230010000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.515110000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.800310000.9868    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9994.083110000.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.800310001.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.948110001.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.661710001.8113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  1  0  0  0  0
  1 24  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  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
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
M  CHG  1  20   1
M  END
> <DATABASE_ID>
HMDB0013208

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H42NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(23)24-20-19-22(2,3)4/h10-11H,5-9,12-20H2,1-4H3/q+1/b11-10-

> <INCHI_KEY>
KZSMYKYPFGHWQV-KHPPLWFESA-N

> <FORMULA>
C21H42NO2

> <MOLECULAR_WEIGHT>
340.571

> <EXACT_MASS>
340.321006017

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
44.84615740830952

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{2-[(9Z)-hexadec-9-enoyloxy]ethyl}trimethylazanium

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
1.896863082861588

> <ALOGPS_LOGS>
-7.51

> <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>
116.90199999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2-[(9Z)-hexadec-9-enoyloxy]ethyl}trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0013208 (9-Hexadecenoylcholine)

HMDB0013208
     RDKit          3D
9-Hexadecenoylcholine
 66 65  0  0  0  0  0  0  0  0999 V2000
   -9.9211    2.2149    0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8677    1.7327   -0.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5957    0.3047   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5792   -0.3496   -1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2261    0.3018   -1.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6404    0.2843    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4754   -1.0875    0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2949   -1.5622    1.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0156   -0.8439    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056   -1.5016    0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -0.6727    0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1106   -0.5435    1.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    0.2328    1.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868   -0.1227    1.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -0.2694   -0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0543   -0.5537   -0.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516   -1.6725   -0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369    0.4956   -0.9891 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2168    0.4612   -1.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9906    0.0442   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3968    0.0250   -0.2790 N   0  0  0  0  0  4  0  0  0  0  0  0
    8.6986   -0.1174   -1.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0433   -1.0776    0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0623    1.2422    0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5117    1.3773    0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6249    2.9325   -0.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4379    2.7197    1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3309    1.8476   -1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9799    2.3810   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5597   -0.2582   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3278    0.1588    0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4552   -1.4047   -0.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9175   -0.3655   -2.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5478   -0.3193   -1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1861    1.3205   -1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3959    0.7839    0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7580    0.9332    0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3936   -1.7062    0.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3180   -2.6073    1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    0.2140    0.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5849   -0.9437    2.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628   -2.4998    0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3366   -1.5774   -0.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1134   -1.0901   -0.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0671    0.3378   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8870    0.0401    2.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0831   -1.5172    2.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    0.4024    2.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841    1.3347    1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421   -1.0295    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462    0.6808    1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0225   -1.1129   -0.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3529    0.6320   -1.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5303    1.5150   -1.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4891   -0.1876   -2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6748   -0.9197    0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7954    0.8175    0.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    0.7079   -2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8215   -0.0816   -1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3954   -1.1099   -2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1388   -0.8212    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7023   -1.1494    1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8934   -1.9851   -0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1067    0.9957    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0655    1.9425   -0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5592    1.6459    1.0769 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  2  0
  8  9  1  0
  9 10  1  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  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 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
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 24 65  1  0
 24 66  1  0
M  CHG  1  21   1
M  END
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PDB for HMDB0013208 (9-Hexadecenoylcholine)

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8662.3028668.509   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.6378667.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8664.9718668.509   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.3058667.740   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8667.6408668.509   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8668.9758667.740   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.3118668.509   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8671.6438667.740   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8672.9798668.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8674.5198668.509   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8675.8558667.740   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8677.1878668.509   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8678.5238667.740   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8679.8598668.509   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8681.1918667.740   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8682.5278668.509   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8660.9648667.740   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8659.6298668.509   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8658.2958667.740   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    8656.9618668.509   0.000  0.00  0.00           N+1
HETATM   21  C   UNK     0    8655.6228667.736   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8656.9618670.048   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8655.3708669.432   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8662.3028670.048   0.000  0.00  0.00           O+0
CONECT    1    2   17   24                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    1   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24    1                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END
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3D PDB for HMDB0013208 (9-Hexadecenoylcholine)

COMPND    HMDB0013208
HETATM    1  C1  UNL     1      -9.921   2.215   0.443  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.868   1.733  -0.562  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.596   0.305  -0.253  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.579  -0.350  -1.138  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.226   0.302  -1.093  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.640   0.284   0.312  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.475  -1.088   0.821  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.295  -1.562   1.170  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.016  -0.844   1.115  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.006  -1.502   0.224  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.701  -0.673   0.201  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.111  -0.543   1.547  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.125   0.233   1.646  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.387  -0.123   1.027  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.565  -0.269  -0.428  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.054  -0.554  -0.618  1.00  0.00           C  
HETATM   17  O1  UNL     1       4.552  -1.673  -0.449  1.00  0.00           O  
HETATM   18  O2  UNL     1       4.837   0.496  -0.989  1.00  0.00           O  
HETATM   19  C17 UNL     1       6.217   0.461  -1.214  1.00  0.00           C  
HETATM   20  C18 UNL     1       6.991   0.044  -0.003  1.00  0.00           C  
HETATM   21  N1  UNL     1       8.397   0.025  -0.279  1.00  0.00           N1+
HETATM   22  C19 UNL     1       8.699  -0.117  -1.687  1.00  0.00           C  
HETATM   23  C20 UNL     1       9.043  -1.078   0.406  1.00  0.00           C  
HETATM   24  C21 UNL     1       9.062   1.242   0.175  1.00  0.00           C  
HETATM   25  H1  UNL     1     -10.512   1.377   0.849  1.00  0.00           H  
HETATM   26  H2  UNL     1     -10.625   2.933  -0.007  1.00  0.00           H  
HETATM   27  H3  UNL     1      -9.438   2.720   1.304  1.00  0.00           H  
HETATM   28  H4  UNL     1      -9.331   1.848  -1.553  1.00  0.00           H  
HETATM   29  H5  UNL     1      -7.980   2.381  -0.398  1.00  0.00           H  
HETATM   30  H6  UNL     1      -9.560  -0.258  -0.391  1.00  0.00           H  
HETATM   31  H7  UNL     1      -8.328   0.159   0.814  1.00  0.00           H  
HETATM   32  H8  UNL     1      -7.455  -1.405  -0.819  1.00  0.00           H  
HETATM   33  H9  UNL     1      -7.918  -0.365  -2.193  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.548  -0.319  -1.722  1.00  0.00           H  
HETATM   35  H11 UNL     1      -6.186   1.321  -1.471  1.00  0.00           H  
HETATM   36  H12 UNL     1      -6.396   0.784   0.998  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.758   0.933   0.383  1.00  0.00           H  
HETATM   38  H14 UNL     1      -6.394  -1.706   0.897  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.318  -2.607   1.534  1.00  0.00           H  
HETATM   40  H16 UNL     1      -3.037   0.214   0.919  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.585  -0.944   2.166  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.763  -2.500   0.632  1.00  0.00           H  
HETATM   43  H19 UNL     1      -2.337  -1.577  -0.829  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.113  -1.090  -0.600  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.067   0.338  -0.170  1.00  0.00           H  
HETATM   46  H22 UNL     1      -0.887   0.040   2.164  1.00  0.00           H  
HETATM   47  H23 UNL     1      -0.083  -1.517   2.109  1.00  0.00           H  
HETATM   48  H24 UNL     1       1.370   0.402   2.768  1.00  0.00           H  
HETATM   49  H25 UNL     1       0.884   1.335   1.368  1.00  0.00           H  
HETATM   50  H26 UNL     1       2.842  -1.029   1.580  1.00  0.00           H  
HETATM   51  H27 UNL     1       3.146   0.681   1.347  1.00  0.00           H  
HETATM   52  H28 UNL     1       2.023  -1.113  -0.914  1.00  0.00           H  
HETATM   53  H29 UNL     1       2.353   0.632  -1.018  1.00  0.00           H  
HETATM   54  H30 UNL     1       6.530   1.515  -1.449  1.00  0.00           H  
HETATM   55  H31 UNL     1       6.489  -0.188  -2.085  1.00  0.00           H  
HETATM   56  H32 UNL     1       6.675  -0.920   0.425  1.00  0.00           H  
HETATM   57  H33 UNL     1       6.795   0.818   0.790  1.00  0.00           H  
HETATM   58  H34 UNL     1       8.331   0.708  -2.308  1.00  0.00           H  
HETATM   59  H35 UNL     1       9.822  -0.082  -1.764  1.00  0.00           H  
HETATM   60  H36 UNL     1       8.395  -1.110  -2.064  1.00  0.00           H  
HETATM   61  H37 UNL     1      10.139  -0.821   0.460  1.00  0.00           H  
HETATM   62  H38 UNL     1       8.702  -1.149   1.449  1.00  0.00           H  
HETATM   63  H39 UNL     1       8.893  -1.985  -0.189  1.00  0.00           H  
HETATM   64  H40 UNL     1      10.107   0.996   0.451  1.00  0.00           H  
HETATM   65  H41 UNL     1       9.065   1.942  -0.667  1.00  0.00           H  
HETATM   66  H42 UNL     1       8.559   1.646   1.077  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7   36   37
CONECT    7    8    8   38
CONECT    8    9   39
CONECT    9   10   40   41
CONECT   10   11   42   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   17   18
CONECT   18   19
CONECT   19   20   54   55
CONECT   20   21   56   57
CONECT   21   22   23   24
CONECT   22   58   59   60
CONECT   23   61   62   63
CONECT   24   64   65   66
END
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SMILES for HMDB0013208 (9-Hexadecenoylcholine)

CCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C
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INCHI for HMDB0013208 (9-Hexadecenoylcholine)

InChI=1S/C21H42NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(23)24-20-19-22(2,3)4/h10-11H,5-9,12-20H2,1-4H3/q+1/b11-10-
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Choline palmitoleateHMDB
PalmitoloelycholineHMDB
9-HexadecenoylcholineHMDB
Chemical FormulaC21H42NO2
Average Molecular Weight340.571
Monoisotopic Molecular Weight340.321006017
IUPAC Name{2-[(9Z)-hexadec-9-enoyloxy]ethyl}trimethylazanium
Traditional Name{2-[(9Z)-hexadec-9-enoyloxy]ethyl}trimethylazanium
CAS Registry Number943438-47-9
SMILES
CCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C21H42NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(23)24-20-19-22(2,3)4/h10-11H,5-9,12-20H2,1-4H3/q+1/b11-10-
InChI KeyKZSMYKYPFGHWQV-KHPPLWFESA-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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentAcyl cholines
Alternative Parents
Substituents
  • Acyl choline
  • Fatty acid ester
  • Fatty acyl
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.2e-05 g/LALOGPS
logP2.58ALOGPS
logP1.9ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity116.9 m³·mol⁻¹ChemAxon
Polarizability44.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+190.94230932474
DeepCCS[M-H]-188.39130932474
DeepCCS[M-2H]-221.59230932474
DeepCCS[M+Na]+197.28530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9-HexadecenoylcholineCCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C2620.3Standard polar33892256
9-HexadecenoylcholineCCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C2106.4Standard non polar33892256
9-HexadecenoylcholineCCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C2338.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9-Hexadecenoylcholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9-Hexadecenoylcholine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029334
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]