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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-08 16:34:12 UTC

Update Date

2022-11-30 19:24:25 UTC

HMDB ID

HMDB0112170

Secondary Accession Numbers

None

Metabolite Identification

Common Name

FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E))

Description

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are endogenous lipids found in adipose tissue and serum that correlate with insulin sensitivity and are reduced in insulin-resistant humans. Structurally, they are characterized by a branched ester linkage between a fatty acid and a hydroxy-fatty acid. Different positions of the branched ester on the hydroxy fatty acid results in different isomers. FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)), in particular, is formed from the condensation of the carboxy group of docosahexaenoic acid (DHA) with the hydroxy group of 13-hydroxyoctadecadienoic acid. It is alternatively named 13-DHAHLA since it is the 13-hydroxy isomer of the DHAHLA (docosahexaenoic acid-hydroxylinoleic acid) family.

Structure

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

  Mrv1652309081718342D          

 60 59  0  0  0  0            999 V2000
    7.8375    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   10.7171    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   10.7171    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   10.0026    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    8.5737    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    7.1447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    5.7158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000    5.7158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    6.4302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    6.1283    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    5.7158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 20  1  0  0  0  0
 23 19  1  0  0  0  0
 24 21  1  0  0  0  0
 25 22  1  0  0  0  0
 26 23  1  0  0  0  0
 27 24  2  0  0  0  0
 28 25  1  0  0  0  0
 29 26  2  0  0  0  0
 30  6  1  0  0  0  0
 31 27  1  0  0  0  0
 32 28  1  0  0  0  0
 33 29  1  0  0  0  0
 34 30  1  0  0  0  0
 35 31  2  0  0  0  0
 36 32  1  0  0  0  0
 37 33  1  0  0  0  0
 38 34  1  0  0  0  0
 38 35  1  0  0  0  0
 39 36  1  0  0  0  0
 40 37  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 38  1  0  0  0  0
 44 40  1  0  0  0  0
 45  5  1  0  0  0  0
 46  7  1  0  0  0  0
 47  9  1  0  0  0  0
 48 10  1  0  0  0  0
 49 12  1  0  0  0  0
 50 13  1  0  0  0  0
 51 15  1  0  0  0  0
 52 16  1  0  0  0  0
 53 18  1  0  0  0  0
 54 19  1  0  0  0  0
 55 24  1  0  0  0  0
 56 26  1  0  0  0  0
 57 27  1  0  0  0  0
 58 29  1  0  0  0  0
 59 31  1  0  0  0  0
 60 35  1  0  0  0  0
M  END

HMDB0112170
     RDKit          3D
FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E))
106105  0  0  0  0  0  0  0  0999 V2000
   14.6067    1.0094    0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1244    1.2957    0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    2.5120   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9053    2.5951   -1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1090    1.5664   -1.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2077    0.1754   -1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1922   -0.5121   -0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8445   -0.0065   -0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8219   -0.7768   -1.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0520   -0.1411   -2.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0269   -0.9183   -3.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7327   -0.3664   -2.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558   -1.0436   -2.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8157   -2.4305   -1.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197   -3.0219   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321   -2.5670    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6012   -1.2376    1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7619   -0.0107    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8629    0.9773    0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5369    0.9417    0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4223    1.0256   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8578    0.9645    0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808    2.0098    1.1786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4883   -0.2357    0.9610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7449   -0.2857    1.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6786   -0.8270    0.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4779   -0.0167    0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3875   -0.5208   -0.9626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1738    0.2550   -1.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2576    1.7251   -1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7305    2.0140   -1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9918    1.3371    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3292    1.5140    0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5499    1.0143    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9796    1.4739   -1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3340    0.8339   -1.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2732   -0.6306   -1.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2315   -1.2956   -1.6279 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4511   -1.3791   -1.9298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212   -1.1240    2.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5591   -1.3202    3.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8470   -1.9706    3.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8864   -1.4822    2.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3002   -0.0339    3.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9071    0.1703    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1751    1.9088    0.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8460    0.7521   -0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0988    1.5849    1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5010    0.4409    0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2695    3.4844    0.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7395    3.6405   -1.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3537    1.5707   -2.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0150    1.9015   -1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1284   -0.4267   -1.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3604   -1.5689   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6387   -0.2183    0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6661    1.0531   -0.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7534   -1.8462   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1210    0.9190   -2.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1870   -0.6652   -4.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2016   -1.9782   -3.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5650    0.6954   -2.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7641   -0.5197   -2.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9199   -2.9379   -2.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6652   -2.8868   -2.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286   -4.1799   -0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5622   -3.4137    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366   -1.2074    1.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4824   -1.2334    1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7689    0.1704    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042    1.8423   -0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4209    1.8658    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895    0.0898    1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5424    1.9991   -0.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4914    0.2340   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    0.7390    2.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7245   -1.8822    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974    1.0285    0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4022   -1.6075   -1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8309   -0.2601   -2.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6169    2.1776   -0.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0638    2.1950   -2.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8506    3.1159   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2908    1.6921   -2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7089    0.2226    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1997    1.6958    0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2900    1.0350    1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4598    2.6180    1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4058    1.2952    0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5347   -0.1300    0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3376    1.1226   -2.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0693    2.5659   -1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6511    1.3174   -2.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0994    1.0842   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7154   -1.6475   -2.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680   -0.8161    3.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2492   -2.1768    2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8406   -0.2526    4.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0743   -1.7167    4.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6516   -3.0605    3.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv1652309081718342D          

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    2.0625    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
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  7  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
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 21 20  1  0  0  0  0
 22 20  1  0  0  0  0
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 30  6  1  0  0  0  0
 31 27  1  0  0  0  0
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 38 34  1  0  0  0  0
 38 35  1  0  0  0  0
 39 36  1  0  0  0  0
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 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 38  1  0  0  0  0
 44 40  1  0  0  0  0
 45  5  1  0  0  0  0
 46  7  1  0  0  0  0
 47  9  1  0  0  0  0
 48 10  1  0  0  0  0
 49 12  1  0  0  0  0
 50 13  1  0  0  0  0
 51 15  1  0  0  0  0
 52 16  1  0  0  0  0
 53 18  1  0  0  0  0
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 55 24  1  0  0  0  0
 56 26  1  0  0  0  0
 57 27  1  0  0  0  0
 58 29  1  0  0  0  0
 59 31  1  0  0  0  0
 60 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0112170

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CC)=C(/[H])C\C([H])=C(\[H])CC([H])=C([H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCC(=O)OC(CCCCC)C(\[H])=C(/[H])C([H])=C([H])CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C40H62O4/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-19-23-26-29-33-37-40(43)44-38(34-30-6-4-2)35-31-27-24-21-20-22-25-28-32-36-39(41)42/h5,7,9-10,12-13,15-16,18-19,24,26-27,29,31,35,38H,3-4,6,8,11,14,17,20-23,25,28,30,32-34,36-37H2,1-2H3,(H,41,42)/b7-5-,10-9-,13-12-,16-15-,19-18-,27-24-,29-26-,35-31+

> <INCHI_KEY>
LNYAZDYWZJMASB-DHOIVBRASA-N

> <FORMULA>
C40H62O4

> <MOLECULAR_WEIGHT>
606.932

> <EXACT_MASS>
606.464810476

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
73.96874980686147

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z,11E)-13-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]octadeca-9,11-dienoic acid

> <ALOGPS_LOGP>
8.85

> <JCHEM_LOGP>
12.608001679666666

> <ALOGPS_LOGS>
-7.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9881672839042

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0556242884697395

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
197.93130000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
30

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.82e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9Z,11E)-13-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]octadeca-9,11-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0112170
     RDKit          3D
FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E))
106105  0  0  0  0  0  0  0  0999 V2000
   14.6067    1.0094    0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1244    1.2957    0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    2.5120   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1090    1.5664   -1.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2077    0.1754   -1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1922   -0.5121   -0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8445   -0.0065   -0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8219   -0.7768   -1.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0520   -0.1411   -2.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0269   -0.9183   -3.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7558   -1.0436   -2.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8629    0.9773    0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4223    1.0256   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8578    0.9645    0.7186 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8864   -1.4822    2.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3002   -0.0339    3.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9071    0.1703    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6387   -0.2183    0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6661    1.0531   -0.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7534   -1.8462   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1210    0.9190   -2.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1870   -0.6652   -4.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2016   -1.9782   -3.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5650    0.6954   -2.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7641   -0.5197   -2.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9199   -2.9379   -2.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6652   -2.8868   -2.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286   -4.1799   -0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5622   -3.4137    1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366   -1.2074    1.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4824   -1.2334    1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7689    0.1704    0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042    1.8423   -0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4209    1.8658    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895    0.0898    1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5424    1.9991   -0.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4914    0.2340   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    0.7390    2.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7245   -1.8822    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974    1.0285    0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4022   -1.6075   -1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8309   -0.2601   -2.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6169    2.1776   -0.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0638    2.1950   -2.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8506    3.1159   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2908    1.6921   -2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7089    0.2226    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1997    1.6958    0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2900    1.0350    1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4598    2.6180    1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4058    1.2952    0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5347   -0.1300    0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3376    1.1226   -2.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0693    2.5659   -1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6511    1.3174   -2.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0994    1.0842   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7154   -1.6475   -2.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680   -0.8161    3.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2492   -2.1768    2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8406   -0.2526    4.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0743   -1.7167    4.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6516   -3.0605    3.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3278   -2.0995    4.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8607   -2.0586    3.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8640   -1.7623    1.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2255    0.1324    4.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3483    0.1437    2.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5651    0.6190    2.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 37 39  1  0
 25 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  2 48  1  0
  2 49  1  0
  3 50  1  0
  4 51  1  0
  5 52  1  0
  5 53  1  0
  6 54  1  0
  7 55  1  0
  8 56  1  0
  8 57  1  0
  9 58  1  0
 10 59  1  0
 11 60  1  0
 11 61  1  0
 12 62  1  0
 13 63  1  0
 14 64  1  0
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 15 66  1  0
 16 67  1  0
 17 68  1  0
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 33 88  1  0
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 35 91  1  0
 35 92  1  0
 36 93  1  0
 36 94  1  0
 39 95  1  0
 40 96  1  0
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 41 98  1  0
 41 99  1  0
 42100  1  0
 42101  1  0
 43102  1  0
 43103  1  0
 44104  1  0
 44105  1  0
 44106  1  0
M  END

HEADER    PROTEIN                                 08-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-17         0                                  
HETATM    1  C   UNK     0      14.630  17.338   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.540   8.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.090  17.338   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   6.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.320  18.672   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.770   6.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.780  18.672   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.010  17.338   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.470  17.338   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.700  16.004   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.470  14.670   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.700  13.337   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.470  12.003   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.010  12.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.780  10.669   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.010   9.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.470   9.336   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.700  10.669   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.160  10.669   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.390   9.336   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.850   9.336   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.080   8.002   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.540   5.335   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.850   6.668   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.080   5.335   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.080  -2.667   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.390   6.668   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       5.390  -4.001   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       3.080  -5.335   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       7.700   5.335   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       5.390   4.001   0.000  0.00  0.00           O+0
HETATM   45  H   UNK     0      13.090  20.005   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      10.010  20.005   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       7.700  18.672   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.160  16.004   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       6.160  13.337   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       9.240  10.669   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      12.320  10.669   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0      10.780   8.002   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.930  12.003   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.826  11.439   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.080  10.669   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.850  -1.334   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.540   8.002   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.390   1.334   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.540   2.667   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7   45                                                  
CONECT    6    4   30                                                       
CONECT    7    5    8   46                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   47                                                  
CONECT   10    9   11   48                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   49                                                  
CONECT   13   12   14   50                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   51                                                  
CONECT   16   15   17   52                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   53                                                  
CONECT   19   18   23   54                                                  
CONECT   20   21   22                                                       
CONECT   21   20   24                                                       
CONECT   22   20   25                                                       
CONECT   23   19   26                                                       
CONECT   24   21   27   55                                                  
CONECT   25   22   28                                                       
CONECT   26   23   29   56                                                  
CONECT   27   24   31   57                                                  
CONECT   28   25   32                                                       
CONECT   29   26   33   58                                                  
CONECT   30    6   34                                                       
CONECT   31   27   35   59                                                  
CONECT   32   28   36                                                       
CONECT   33   29   37                                                       
CONECT   34   30   38                                                       
CONECT   35   31   38   60                                                  
CONECT   36   32   39                                                       
CONECT   37   33   40                                                       
CONECT   38   34   35   44                                                  
CONECT   39   36   41   42                                                  
CONECT   40   37   43   44                                                  
CONECT   41   39                                                            
CONECT   42   39                                                            
CONECT   43   40                                                            
CONECT   44   38   40                                                       
CONECT   45    5                                                            
CONECT   46    7                                                            
CONECT   47    9                                                            
CONECT   48   10                                                            
CONECT   49   12                                                            
CONECT   50   13                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   18                                                            
CONECT   54   19                                                            
CONECT   55   24                                                            
CONECT   56   26                                                            
CONECT   57   27                                                            
CONECT   58   29                                                            
CONECT   59   31                                                            
CONECT   60   35                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  118    0
END

COMPND    HMDB0112170
HETATM    1  C1  UNL     1      14.607   1.009   0.347  1.00  0.00           C  
HETATM    2  C2  UNL     1      13.124   1.296   0.553  1.00  0.00           C  
HETATM    3  C3  UNL     1      12.758   2.512  -0.170  1.00  0.00           C  
HETATM    4  C4  UNL     1      11.905   2.595  -1.139  1.00  0.00           C  
HETATM    5  C5  UNL     1      11.109   1.566  -1.765  1.00  0.00           C  
HETATM    6  C6  UNL     1      11.208   0.175  -1.397  1.00  0.00           C  
HETATM    7  C7  UNL     1      10.192  -0.512  -0.888  1.00  0.00           C  
HETATM    8  C8  UNL     1       8.845  -0.006  -0.618  1.00  0.00           C  
HETATM    9  C9  UNL     1       7.822  -0.777  -1.419  1.00  0.00           C  
HETATM   10  C10 UNL     1       7.052  -0.141  -2.277  1.00  0.00           C  
HETATM   11  C11 UNL     1       6.027  -0.918  -3.080  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.733  -0.366  -2.735  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.756  -1.044  -2.193  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.816  -2.430  -1.859  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.720  -3.022  -0.563  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.632  -2.567   0.630  1.00  0.00           C  
HETATM   17  C17 UNL     1       3.601  -1.238   1.204  1.00  0.00           C  
HETATM   18  C18 UNL     1       3.762  -0.011   0.493  1.00  0.00           C  
HETATM   19  C19 UNL     1       2.863   0.977   0.369  1.00  0.00           C  
HETATM   20  C20 UNL     1       1.537   0.942   0.964  1.00  0.00           C  
HETATM   21  C21 UNL     1       0.422   1.026  -0.074  1.00  0.00           C  
HETATM   22  C22 UNL     1      -0.858   0.965   0.719  1.00  0.00           C  
HETATM   23  O1  UNL     1      -1.381   2.010   1.179  1.00  0.00           O  
HETATM   24  O2  UNL     1      -1.488  -0.236   0.961  1.00  0.00           O  
HETATM   25  C23 UNL     1      -2.745  -0.286   1.739  1.00  0.00           C  
HETATM   26  C24 UNL     1      -3.679  -0.827   0.730  1.00  0.00           C  
HETATM   27  C25 UNL     1      -4.478  -0.017   0.020  1.00  0.00           C  
HETATM   28  C26 UNL     1      -5.387  -0.521  -0.963  1.00  0.00           C  
HETATM   29  C27 UNL     1      -6.174   0.255  -1.657  1.00  0.00           C  
HETATM   30  C28 UNL     1      -6.258   1.725  -1.550  1.00  0.00           C  
HETATM   31  C29 UNL     1      -7.730   2.014  -1.150  1.00  0.00           C  
HETATM   32  C30 UNL     1      -7.992   1.337   0.138  1.00  0.00           C  
HETATM   33  C31 UNL     1      -9.329   1.514   0.714  1.00  0.00           C  
HETATM   34  C32 UNL     1     -10.550   1.014   0.082  1.00  0.00           C  
HETATM   35  C33 UNL     1     -10.980   1.474  -1.252  1.00  0.00           C  
HETATM   36  C34 UNL     1     -12.334   0.834  -1.610  1.00  0.00           C  
HETATM   37  C35 UNL     1     -12.273  -0.631  -1.715  1.00  0.00           C  
HETATM   38  O3  UNL     1     -11.231  -1.296  -1.628  1.00  0.00           O  
HETATM   39  O4  UNL     1     -13.451  -1.379  -1.930  1.00  0.00           O  
HETATM   40  C36 UNL     1      -2.521  -1.124   2.928  1.00  0.00           C  
HETATM   41  C37 UNL     1      -3.559  -1.320   3.929  1.00  0.00           C  
HETATM   42  C38 UNL     1      -4.847  -1.971   3.753  1.00  0.00           C  
HETATM   43  C39 UNL     1      -5.886  -1.482   2.839  1.00  0.00           C  
HETATM   44  C40 UNL     1      -6.300  -0.034   3.110  1.00  0.00           C  
HETATM   45  H1  UNL     1      14.907   0.170   1.026  1.00  0.00           H  
HETATM   46  H2  UNL     1      15.175   1.909   0.634  1.00  0.00           H  
HETATM   47  H3  UNL     1      14.846   0.752  -0.689  1.00  0.00           H  
HETATM   48  H4  UNL     1      13.099   1.585   1.693  1.00  0.00           H  
HETATM   49  H5  UNL     1      12.501   0.441   0.502  1.00  0.00           H  
HETATM   50  H6  UNL     1      13.269   3.484   0.146  1.00  0.00           H  
HETATM   51  H7  UNL     1      11.740   3.641  -1.585  1.00  0.00           H  
HETATM   52  H8  UNL     1      11.354   1.571  -2.911  1.00  0.00           H  
HETATM   53  H9  UNL     1      10.015   1.901  -1.836  1.00  0.00           H  
HETATM   54  H10 UNL     1      12.128  -0.427  -1.542  1.00  0.00           H  
HETATM   55  H11 UNL     1      10.360  -1.569  -0.638  1.00  0.00           H  
HETATM   56  H12 UNL     1       8.639  -0.218   0.464  1.00  0.00           H  
HETATM   57  H13 UNL     1       8.666   1.053  -0.747  1.00  0.00           H  
HETATM   58  H14 UNL     1       7.753  -1.846  -1.260  1.00  0.00           H  
HETATM   59  H15 UNL     1       7.121   0.919  -2.434  1.00  0.00           H  
HETATM   60  H16 UNL     1       6.187  -0.665  -4.184  1.00  0.00           H  
HETATM   61  H17 UNL     1       6.202  -1.978  -3.020  1.00  0.00           H  
HETATM   62  H18 UNL     1       4.565   0.695  -2.947  1.00  0.00           H  
HETATM   63  H19 UNL     1       2.764  -0.520  -2.013  1.00  0.00           H  
HETATM   64  H20 UNL     1       2.920  -2.938  -2.451  1.00  0.00           H  
HETATM   65  H21 UNL     1       4.665  -2.887  -2.462  1.00  0.00           H  
HETATM   66  H22 UNL     1       3.729  -4.180  -0.619  1.00  0.00           H  
HETATM   67  H23 UNL     1       3.562  -3.414   1.432  1.00  0.00           H  
HETATM   68  H24 UNL     1       2.737  -1.207   1.951  1.00  0.00           H  
HETATM   69  H25 UNL     1       4.482  -1.233   1.978  1.00  0.00           H  
HETATM   70  H26 UNL     1       4.769   0.170   0.032  1.00  0.00           H  
HETATM   71  H27 UNL     1       3.204   1.842  -0.231  1.00  0.00           H  
HETATM   72  H28 UNL     1       1.421   1.866   1.619  1.00  0.00           H  
HETATM   73  H29 UNL     1       1.389   0.090   1.634  1.00  0.00           H  
HETATM   74  H30 UNL     1       0.542   1.999  -0.590  1.00  0.00           H  
HETATM   75  H31 UNL     1       0.491   0.234  -0.820  1.00  0.00           H  
HETATM   76  H32 UNL     1      -3.037   0.739   2.032  1.00  0.00           H  
HETATM   77  H33 UNL     1      -3.725  -1.882   0.555  1.00  0.00           H  
HETATM   78  H34 UNL     1      -4.397   1.029   0.230  1.00  0.00           H  
HETATM   79  H35 UNL     1      -5.402  -1.608  -1.116  1.00  0.00           H  
HETATM   80  H36 UNL     1      -6.831  -0.260  -2.389  1.00  0.00           H  
HETATM   81  H37 UNL     1      -5.617   2.178  -0.796  1.00  0.00           H  
HETATM   82  H38 UNL     1      -6.064   2.195  -2.528  1.00  0.00           H  
HETATM   83  H39 UNL     1      -7.851   3.116  -1.069  1.00  0.00           H  
HETATM   84  H40 UNL     1      -8.291   1.692  -2.027  1.00  0.00           H  
HETATM   85  H41 UNL     1      -7.709   0.223   0.072  1.00  0.00           H  
HETATM   86  H42 UNL     1      -7.200   1.696   0.886  1.00  0.00           H  
HETATM   87  H43 UNL     1      -9.290   1.035   1.761  1.00  0.00           H  
HETATM   88  H44 UNL     1      -9.460   2.618   1.002  1.00  0.00           H  
HETATM   89  H45 UNL     1     -11.406   1.295   0.808  1.00  0.00           H  
HETATM   90  H46 UNL     1     -10.535  -0.130   0.128  1.00  0.00           H  
HETATM   91  H47 UNL     1     -10.338   1.123  -2.098  1.00  0.00           H  
HETATM   92  H48 UNL     1     -11.069   2.566  -1.326  1.00  0.00           H  
HETATM   93  H49 UNL     1     -12.651   1.317  -2.561  1.00  0.00           H  
HETATM   94  H50 UNL     1     -13.099   1.084  -0.827  1.00  0.00           H  
HETATM   95  H51 UNL     1     -13.715  -1.647  -2.880  1.00  0.00           H  
HETATM   96  H52 UNL     1      -1.568  -0.816   3.477  1.00  0.00           H  
HETATM   97  H53 UNL     1      -2.249  -2.177   2.542  1.00  0.00           H  
HETATM   98  H54 UNL     1      -3.841  -0.253   4.348  1.00  0.00           H  
HETATM   99  H55 UNL     1      -3.074  -1.717   4.918  1.00  0.00           H  
HETATM  100  H56 UNL     1      -4.652  -3.061   3.479  1.00  0.00           H  
HETATM  101  H57 UNL     1      -5.328  -2.100   4.782  1.00  0.00           H  
HETATM  102  H58 UNL     1      -6.861  -2.059   3.199  1.00  0.00           H  
HETATM  103  H59 UNL     1      -5.864  -1.762   1.808  1.00  0.00           H  
HETATM  104  H60 UNL     1      -6.226   0.132   4.221  1.00  0.00           H  
HETATM  105  H61 UNL     1      -7.348   0.144   2.846  1.00  0.00           H  
HETATM  106  H62 UNL     1      -5.565   0.619   2.625  1.00  0.00           H  
CONECT    1    2   45   46   47
CONECT    2    3   48   49
CONECT    3    4    4   50
CONECT    4    5   51
CONECT    5    6   52   53
CONECT    6    7    7   54
CONECT    7    8   55
CONECT    8    9   56   57
CONECT    9   10   10   58
CONECT   10   11   59
CONECT   11   12   60   61
CONECT   12   13   13   62
CONECT   13   14   63
CONECT   14   15   64   65
CONECT   15   16   16   66
CONECT   16   17   67
CONECT   17   18   68   69
CONECT   18   19   19   70
CONECT   19   20   71
CONECT   20   21   72   73
CONECT   21   22   74   75
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   26   40   76
CONECT   26   27   27   77
CONECT   27   28   78
CONECT   28   29   29   79
CONECT   29   30   80
CONECT   30   31   81   82
CONECT   31   32   83   84
CONECT   32   33   85   86
CONECT   33   34   87   88
CONECT   34   35   89   90
CONECT   35   36   91   92
CONECT   36   37   93   94
CONECT   37   38   38   39
CONECT   39   95
CONECT   40   41   96   97
CONECT   41   42   98   99
CONECT   42   43  100  101
CONECT   43   44  102  103
CONECT   44  104  105  106
END

HMDB0112170
     RDKit          3D
FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E))
106105  0  0  0  0  0  0  0  0999 V2000
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   13.1244    1.2957    0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    2.5120   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9053    2.5951   -1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1090    1.5664   -1.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2077    0.1754   -1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1922   -0.5121   -0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8445   -0.0065   -0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8219   -0.7768   -1.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0520   -0.1411   -2.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0269   -0.9183   -3.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7327   -0.3664   -2.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558   -1.0436   -2.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8157   -2.4305   -1.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5369    0.9417    0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4223    1.0256   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9918    1.3371    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3292    1.5140    0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5499    1.0143    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9796    1.4739   -1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3340    0.8339   -1.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2732   -0.6306   -1.7154 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -13.4511   -1.3791   -1.9298 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5591   -1.3202    3.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8864   -1.4822    2.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4209    1.8658    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895    0.0898    1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6516   -3.0605    3.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8607   -2.0586    3.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
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 11 12  1  0
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 13 14  1  0
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 15 16  2  0
 16 17  1  0
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 20 21  1  0
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 22 24  1  0
 24 25  1  0
 25 26  1  0
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 31 32  1  0
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 35 36  1  0
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 37 39  1  0
 25 40  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(11E)-13-[(4Z,7Z,10Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoyloxy]octadeca-9,11-dienoate	HMDB
FAHFA(22:6/13-O-18:2)	HMDB
13-DHAHLA	HMDB
13-(Docosahexaenoyloxy)octadecadienoic acid	HMDB
Docosahexaenoic acid-13-hydroxylinoleic acid	HMDB
FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E))	HMDB
docosahexaenoic acid-13-hydroxylinoleic acid	SMPDB, HMDB

Chemical Formula

C₄₀H₆₂O₄

Average Molecular Weight

606.932

Monoisotopic Molecular Weight

606.464810476

IUPAC Name

(9Z,11E)-13-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]octadeca-9,11-dienoic acid

Traditional Name

(9Z,11E)-13-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]octadeca-9,11-dienoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CC)=C(/[H])C\C([H])=C(\[H])CC([H])=C([H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCC(=O)OC(CCCCC)C(\[H])=C(/[H])C([H])=C([H])CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C40H62O4/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-19-23-26-29-33-37-40(43)44-38(34-30-6-4-2)35-31-27-24-21-20-22-25-28-32-36-39(41)42/h5,7,9-10,12-13,15-16,18-19,24,26-27,29,31,35,38H,3-4,6,8,11,14,17,20-23,25,28,30,32-34,36-37H2,1-2H3,(H,41,42)/b7-5-,10-9-,13-12-,16-15-,19-18-,27-24-,29-26-,35-31+

InChI Key

LNYAZDYWZJMASB-DHOIVBRASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Fatty acid ester
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0112170)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	8.85	ALOGPS
logP	12.61	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	30	ChemAxon
Refractivity	197.93 m³·mol⁻¹	ChemAxon
Polarizability	73.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	263.14	31661259
DarkChem	[M-H]-	256.024	31661259
DeepCCS	[M+H]+	265.231	30932474
DeepCCS	[M-H]-	263.507	30932474
DeepCCS	[M-2H]-	297.548	30932474
DeepCCS	[M+Na]+	271.56	30932474
AllCCS	[M+H]+	257.6	32859911
AllCCS	[M+H-H2O]+	256.7	32859911
AllCCS	[M+NH4]+	258.3	32859911
AllCCS	[M+Na]+	258.5	32859911
AllCCS	[M-H]-	243.3	32859911
AllCCS	[M+Na-2H]-	249.3	32859911
AllCCS	[M+HCOO]-	256.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E))	[H]\C(CC)=C(/[H])C\C([H])=C(\[H])CC([H])=C([H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCC(=O)OC(CCCCC)C(\[H])=C(/[H])C([H])=C([H])CCCCCCCC(O)=O	6762.3	Standard polar	33892256
FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E))	[H]\C(CC)=C(/[H])C\C([H])=C(\[H])CC([H])=C([H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCC(=O)OC(CCCCC)C(\[H])=C(/[H])C([H])=C([H])CCCCCCCC(O)=O	4154.4	Standard non polar	33892256
FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E))	[H]\C(CC)=C(/[H])C\C([H])=C(\[H])CC([H])=C([H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCC(=O)OC(CCCCC)C(\[H])=C(/[H])C([H])=C([H])CCCCCCCC(O)=O	4519.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)),1TMS,isomer #1	CC/C=C\C/C=C\CC=CC/C=C\C/C=C\C/C=C\CCC(=O)OC(/C=C/C=CCCCCCCCC(=O)O[Si](C)(C)C)CCCCC	4545.3	Semi standard non polar	33892256
FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)),1TBDMS,isomer #1	CC/C=C\C/C=C\CC=CC/C=C\C/C=C\C/C=C\CCC(=O)OC(/C=C/C=CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)CCCCC	4778.6	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 - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) GC-MS (1 TMS) - 70eV, Positive	splash10-0nmi-7359106000-5d078f2812e87542f819	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) GC-MS ("FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)),1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-20	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) 10V, Positive-QTOF	splash10-01p9-0052092000-1fb9b68393709aa651ab	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) 20V, Positive-QTOF	splash10-03fr-1192020000-9e78c8932ba3cfcc3b54	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) 40V, Positive-QTOF	splash10-015c-3191020000-461c77cf8928acca2aa2	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) 10V, Negative-QTOF	splash10-0a4i-0042039000-d10ac50db35e3888bf0b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) 20V, Negative-QTOF	splash10-0a6s-1094031000-a8bafd7fb6dd0b1dc3c2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) 40V, Negative-QTOF	splash10-0a6v-6092000000-502087c4654cf5b194a4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) 10V, Negative-QTOF	splash10-0a4i-0000009000-cb60f89fb1c53ba97586	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) 20V, Negative-QTOF	splash10-0a4i-0000009000-cb60f89fb1c53ba97586	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) 40V, Negative-QTOF	splash10-0bdk-0094004000-82b577cb2bcb62c380e5	2021-09-23	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74849799

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131819631

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

Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB: Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell. 2014 Oct 9;159(2):318-32. doi: 10.1016/j.cell.2014.09.035. [PubMed:25303528 ]
Kuda O, Brezinova M, Rombaldova M, Slavikova B, Posta M, Beier P, Janovska P, Veleba J, Kopecky J Jr, Kudova E, Pelikanova T, Kopecky J: Docosahexaenoic Acid-Derived Fatty Acid Esters of Hydroxy Fatty Acids (FAHFAs) With Anti-inflammatory Properties. Diabetes. 2016 Sep;65(9):2580-90. doi: 10.2337/db16-0385. Epub 2016 Jun 16. [PubMed:27313314 ]

Showing metabocard for FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)) (HMDB0112170)

MOL for HMDB0112170 (FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)))

3D MOL for HMDB0112170 (FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)))

3D SDF for HMDB0112170 (FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)))

3D-SDF for HMDB0112170 (FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)))

PDB for HMDB0112170 (FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)))

3D PDB for HMDB0112170 (FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)))

SMILES for HMDB0112170 (FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)))

INCHI for HMDB0112170 (FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)))

Structure for HMDB0112170 (FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)))

3D Structure for HMDB0112170 (FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/13-O-18:2(9Z,11E)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra