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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-12 11:24:34 UTC

Update Date

2022-11-30 19:56:20 UTC

HMDB ID

HMDB0266526

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0)

Description

PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0), in particular, consists of one chain of one Lipoxin A4 at the C-1 position and one chain of acetyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396 ).

Structure

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

PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0)
  Mrv1652309122113242D          

 38 37  0  0  1  0            999 V2000
   -3.8020    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2262    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9403    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6544    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3686    0.7695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3686    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0827    0.3564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0827   -0.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7968    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5109    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2250    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9391    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6532    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4782    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1923    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9065    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6206    0.3564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -14.6206   -0.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3347    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0489    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7630    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4771    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.1912    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2  9  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
  9  8  1  0  0  0  0
 11 36  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END

HMDB0266526
     RDKit          3D
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0)
 78 77  0  0  0  0  0  0  0  0999 V2000
  -13.3594    0.4944   -1.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0014    0.1990   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3509   -0.9157   -1.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0670   -1.4769   -1.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8039   -0.7038   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8546    0.5153   -0.3581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.1803    0.0396    0.9689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6125    1.2489   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4093    0.7403   -0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3795    1.7112    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1209    1.4201    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174   -0.0208    0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5919   -0.3708    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2380   -0.7997    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4432    0.2784    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302    0.3467    1.2978 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1142    0.9303    2.5914 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7809   -0.8811    1.2134 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2691   -1.8272    2.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1493   -0.4474    1.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7021    0.7302    1.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0489    1.2088    1.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691    0.2820    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -0.7358    0.4264 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4733    0.4518    1.6654 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121   -0.4617    1.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7860   -0.0704   -0.1985 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5002   -1.0723   -1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8242   -1.3066   -0.7034 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3538   -2.4871   -1.8141 P   0  0  0  0  0  5  0  0  0  0  0  0
   10.8644   -2.1505   -3.2261 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0312   -2.6059   -1.8900 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6133   -3.9214   -1.3449 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3040    1.2391   -0.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5966    2.3786   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3480    3.6698   -0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4374    2.2565   -1.0200 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1679    1.3019   -2.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7653   -0.4191   -2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0205    0.9140   -0.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2490   -0.0357    0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5391    1.1879   -0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3208   -0.7398   -2.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1050   -1.7850   -1.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1618   -1.7937   -0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8600   -2.4591   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9600   -1.3356   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5106   -0.4717   -2.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5942    1.1975   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3572   -0.5078    1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7385    2.3590   -0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3216   -0.3071   -0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5866    2.7920    0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    2.1664    0.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5006   -0.6954    0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9444   -1.6705    0.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709   -1.7128    0.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    1.2315    1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4067    1.0635    0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.4855    3.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982   -1.3353    0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -1.3494    3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8054   -1.3448    1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0364   -0.1759    2.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0096    1.6103    1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318    0.5722   -0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2464    2.1705    0.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1132    1.4368    2.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3566   -0.2252    1.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1234   -1.4700    1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7537    0.0421   -0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9513   -2.0541   -0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3580   -0.7841   -2.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3684   -3.1075   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7689   -4.5986   -2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3868    3.4625   -0.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3238    4.0953    0.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8341    4.4036   -1.2234 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 27 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  2 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  6 49  1  6
  7 50  1  0
  8 51  1  0
  9 52  1  0
 10 53  1  0
 11 54  1  0
 12 55  1  0
 13 56  1  0
 14 57  1  0
 15 58  1  0
 16 59  1  6
 17 60  1  0
 18 61  1  6
 19 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 22 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  6
 28 72  1  0
 28 73  1  0
 32 74  1  0
 33 75  1  0
 36 76  1  0
 36 77  1  0
 36 78  1  0
M  END

PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0)
  Mrv1652309122113242D          

 38 37  0  0  1  0            999 V2000
   -3.8020    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2262    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9403    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6544    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3686    0.7695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3686    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0827    0.3564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0827   -0.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7968    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5109    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2250    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9391    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6532    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4782    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1923    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9065    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6206    0.3564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -14.6206   -0.4150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3347    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0489    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7630    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.4771    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.1912    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2236   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2  9  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
  9  8  1  0  0  0  0
 11 36  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0266526

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](COC(=O)CCC[C@@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@H](O)CCCCC)(COP(O)(O)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H41O11P/c1-3-4-9-13-21(27)14-10-7-5-6-8-11-15-23(28)24(29)16-12-17-25(30)34-18-22(36-20(2)26)19-35-37(31,32)33/h5-8,10-11,14-15,21-24,27-29H,3-4,9,12-13,16-19H2,1-2H3,(H2,31,32,33)/b7-5-,8-6+,14-10+,15-11+/t21-,22-,23-,24-/m1/s1

> <INCHI_KEY>
PQQJZVSHZXSGAX-YLIDQWBLSA-N

> <FORMULA>
C25H41O11P

> <MOLECULAR_WEIGHT>
548.566

> <EXACT_MASS>
548.238649138

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
57.981159173806134

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-2-(acetyloxy)-3-{[(5R,6R,7E,9E,11Z,13E,15R)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoyl]oxy}propoxy]phosphonic acid

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.193661550999999

> <ALOGPS_LOGS>
-5.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.343261770797884

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3179879708306976

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5765248174540751

> <JCHEM_POLAR_SURFACE_AREA>
180.05

> <JCHEM_REFRACTIVITY>
141.3948

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-(acetyloxy)-3-{[(5R,6R,7E,9E,11Z,13E,15R)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoyl]oxy}propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0266526
     RDKit          3D
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0)
 78 77  0  0  0  0  0  0  0  0999 V2000
  -13.3594    0.4944   -1.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0014    0.1990   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3509   -0.9157   -1.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0670   -1.4769   -1.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8039   -0.7038   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8546    0.5153   -0.3581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.1803    0.0396    0.9689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6125    1.2489   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4093    0.7403   -0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3795    1.7112    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1209    1.4201    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174   -0.0208    0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5919   -0.3708    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2380   -0.7997    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4432    0.2784    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302    0.3467    1.2978 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1142    0.9303    2.5914 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7809   -0.8811    1.2134 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2691   -1.8272    2.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1493   -0.4474    1.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7021    0.7302    1.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0489    1.2088    1.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691    0.2820    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -0.7358    0.4264 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4733    0.4518    1.6654 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121   -0.4617    1.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7860   -0.0704   -0.1985 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5002   -1.0723   -1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8242   -1.3066   -0.7034 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3538   -2.4871   -1.8141 P   0  0  0  0  0  5  0  0  0  0  0  0
   10.8644   -2.1505   -3.2261 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0312   -2.6059   -1.8900 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6133   -3.9214   -1.3449 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3040    1.2391   -0.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5966    2.3786   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3480    3.6698   -0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4374    2.2565   -1.0200 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1679    1.3019   -2.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7653   -0.4191   -2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0205    0.9140   -0.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2490   -0.0357    0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5391    1.1879   -0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3208   -0.7398   -2.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1050   -1.7850   -1.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1618   -1.7937   -0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8600   -2.4591   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9600   -1.3356   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5106   -0.4717   -2.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5942    1.1975   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3572   -0.5078    1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7385    2.3590   -0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3216   -0.3071   -0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5866    2.7920    0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    2.1664    0.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5006   -0.6954    0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9444   -1.6705    0.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709   -1.7128    0.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    1.2315    1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4067    1.0635    0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.4855    3.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982   -1.3353    0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -1.3494    3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8054   -1.3448    1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0364   -0.1759    2.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0096    1.6103    1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318    0.5722   -0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2464    2.1705    0.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1132    1.4368    2.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3566   -0.2252    1.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1234   -1.4700    1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7537    0.0421   -0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9513   -2.0541   -0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3580   -0.7841   -2.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3684   -3.1075   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7689   -4.5986   -2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3868    3.4625   -0.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3238    4.0953    0.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8341    4.4036   -1.2234 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 27 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  2 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  6 49  1  6
  7 50  1  0
  8 51  1  0
  9 52  1  0
 10 53  1  0
 11 54  1  0
 12 55  1  0
 13 56  1  0
 14 57  1  0
 15 58  1  0
 16 59  1  6
 17 60  1  0
 18 61  1  6
 19 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 22 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  6
 28 72  1  0
 28 73  1  0
 32 74  1  0
 33 75  1  0
 36 76  1  0
 36 77  1  0
 36 78  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0)        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  O   UNK     0      -7.097   0.673   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -1.790   0.671   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0      -0.457   1.441   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0      -1.227   2.775   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.313   0.107   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.877   2.211   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.781   1.440   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.447   0.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.113   1.440   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -3.677  -0.663   0.000  0.00  0.00           H+0
HETATM   11  O   UNK     0      -5.217  -0.663   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -8.423   1.436   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.423   2.876   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -9.756   0.665   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -11.089   1.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.422   0.665   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -13.755   1.436   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -13.755   2.876   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -15.088  -0.775   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -16.421   1.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -19.087   1.436   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -20.420   0.665   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -21.753   1.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -23.293   1.436   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -24.626   0.665   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -25.959   1.436   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -27.292   0.665   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -27.292  -0.775   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -28.625   1.436   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -29.958   0.665   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -31.291   1.436   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -32.624   0.665   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -33.957   1.436   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.551  -1.433   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.551  -2.873   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -7.884  -0.662   0.000  0.00  0.00           C+0
CONECT    1   12    7                                                       
CONECT    2    9    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    1    8                                                       
CONECT    8    7   10   11    9                                             
CONECT    9    2    8                                                       
CONECT   10    8                                                            
CONECT   11    8   36                                                       
CONECT   12    1   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   11   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   74    0
END

COMPND    HMDB0266526
HETATM    1  C1  UNL     1     -13.359   0.494  -1.605  1.00  0.00           C  
HETATM    2  C2  UNL     1     -12.001   0.199  -0.889  1.00  0.00           C  
HETATM    3  C3  UNL     1     -11.351  -0.916  -1.579  1.00  0.00           C  
HETATM    4  C4  UNL     1     -10.067  -1.477  -1.153  1.00  0.00           C  
HETATM    5  C5  UNL     1      -8.804  -0.704  -1.192  1.00  0.00           C  
HETATM    6  C6  UNL     1      -8.855   0.515  -0.358  1.00  0.00           C  
HETATM    7  O1  UNL     1      -9.180   0.040   0.969  1.00  0.00           O  
HETATM    8  C7  UNL     1      -7.612   1.249  -0.140  1.00  0.00           C  
HETATM    9  C8  UNL     1      -6.409   0.740  -0.018  1.00  0.00           C  
HETATM   10  C9  UNL     1      -5.379   1.711   0.192  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.121   1.420   0.343  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.717  -0.021   0.295  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.592  -0.371   0.471  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.238  -0.800   0.682  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.443   0.278   1.014  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.930   0.347   1.298  1.00  0.00           C  
HETATM   17  O2  UNL     1       1.114   0.930   2.591  1.00  0.00           O  
HETATM   18  C16 UNL     1       1.781  -0.881   1.213  1.00  0.00           C  
HETATM   19  O3  UNL     1       1.269  -1.827   2.163  1.00  0.00           O  
HETATM   20  C17 UNL     1       3.149  -0.447   1.766  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.702   0.730   1.051  1.00  0.00           C  
HETATM   22  C19 UNL     1       5.049   1.209   1.476  1.00  0.00           C  
HETATM   23  C20 UNL     1       6.169   0.282   1.173  1.00  0.00           C  
HETATM   24  O4  UNL     1       5.975  -0.736   0.426  1.00  0.00           O  
HETATM   25  O5  UNL     1       7.473   0.452   1.665  1.00  0.00           O  
HETATM   26  C21 UNL     1       8.512  -0.462   1.262  1.00  0.00           C  
HETATM   27  C22 UNL     1       8.786  -0.070  -0.199  1.00  0.00           C  
HETATM   28  C23 UNL     1       9.500  -1.072  -1.002  1.00  0.00           C  
HETATM   29  O6  UNL     1      10.824  -1.307  -0.703  1.00  0.00           O  
HETATM   30  P1  UNL     1      11.354  -2.487  -1.814  1.00  0.00           P  
HETATM   31  O7  UNL     1      10.864  -2.150  -3.226  1.00  0.00           O  
HETATM   32  O8  UNL     1      13.031  -2.606  -1.890  1.00  0.00           O  
HETATM   33  O9  UNL     1      10.613  -3.921  -1.345  1.00  0.00           O  
HETATM   34  O10 UNL     1       9.304   1.239  -0.212  1.00  0.00           O  
HETATM   35  C24 UNL     1       8.597   2.379  -0.629  1.00  0.00           C  
HETATM   36  C25 UNL     1       9.348   3.670  -0.558  1.00  0.00           C  
HETATM   37  O11 UNL     1       7.437   2.257  -1.020  1.00  0.00           O  
HETATM   38  H1  UNL     1     -13.168   1.302  -2.330  1.00  0.00           H  
HETATM   39  H2  UNL     1     -13.765  -0.419  -2.055  1.00  0.00           H  
HETATM   40  H3  UNL     1     -14.020   0.914  -0.826  1.00  0.00           H  
HETATM   41  H4  UNL     1     -12.249  -0.036   0.175  1.00  0.00           H  
HETATM   42  H5  UNL     1     -11.539   1.188  -0.873  1.00  0.00           H  
HETATM   43  H6  UNL     1     -11.321  -0.740  -2.717  1.00  0.00           H  
HETATM   44  H7  UNL     1     -12.105  -1.785  -1.533  1.00  0.00           H  
HETATM   45  H8  UNL     1     -10.162  -1.794  -0.048  1.00  0.00           H  
HETATM   46  H9  UNL     1      -9.860  -2.459  -1.688  1.00  0.00           H  
HETATM   47  H10 UNL     1      -7.960  -1.336  -0.802  1.00  0.00           H  
HETATM   48  H11 UNL     1      -8.511  -0.472  -2.270  1.00  0.00           H  
HETATM   49  H12 UNL     1      -9.594   1.197  -0.754  1.00  0.00           H  
HETATM   50  H13 UNL     1      -8.357  -0.508   1.205  1.00  0.00           H  
HETATM   51  H14 UNL     1      -7.738   2.359  -0.085  1.00  0.00           H  
HETATM   52  H15 UNL     1      -6.322  -0.307  -0.099  1.00  0.00           H  
HETATM   53  H16 UNL     1      -5.587   2.792   0.214  1.00  0.00           H  
HETATM   54  H17 UNL     1      -3.366   2.166   0.508  1.00  0.00           H  
HETATM   55  H18 UNL     1      -4.501  -0.695   0.135  1.00  0.00           H  
HETATM   56  H19 UNL     1      -2.944  -1.670   0.241  1.00  0.00           H  
HETATM   57  H20 UNL     1      -0.771  -1.713   0.626  1.00  0.00           H  
HETATM   58  H21 UNL     1      -1.038   1.231   1.036  1.00  0.00           H  
HETATM   59  H22 UNL     1       1.407   1.063   0.516  1.00  0.00           H  
HETATM   60  H23 UNL     1       0.413   0.485   3.155  1.00  0.00           H  
HETATM   61  H24 UNL     1       1.898  -1.335   0.258  1.00  0.00           H  
HETATM   62  H25 UNL     1       1.341  -1.349   3.036  1.00  0.00           H  
HETATM   63  H26 UNL     1       3.805  -1.345   1.712  1.00  0.00           H  
HETATM   64  H27 UNL     1       3.036  -0.176   2.847  1.00  0.00           H  
HETATM   65  H28 UNL     1       3.010   1.610   1.190  1.00  0.00           H  
HETATM   66  H29 UNL     1       3.732   0.572  -0.055  1.00  0.00           H  
HETATM   67  H30 UNL     1       5.246   2.171   0.941  1.00  0.00           H  
HETATM   68  H31 UNL     1       5.113   1.437   2.557  1.00  0.00           H  
HETATM   69  H32 UNL     1       9.357  -0.225   1.917  1.00  0.00           H  
HETATM   70  H33 UNL     1       8.123  -1.470   1.325  1.00  0.00           H  
HETATM   71  H34 UNL     1       7.754   0.042  -0.643  1.00  0.00           H  
HETATM   72  H35 UNL     1       8.951  -2.054  -0.881  1.00  0.00           H  
HETATM   73  H36 UNL     1       9.358  -0.784  -2.082  1.00  0.00           H  
HETATM   74  H37 UNL     1      13.368  -3.108  -1.094  1.00  0.00           H  
HETATM   75  H38 UNL     1      10.769  -4.599  -2.041  1.00  0.00           H  
HETATM   76  H39 UNL     1      10.387   3.463  -0.808  1.00  0.00           H  
HETATM   77  H40 UNL     1       9.324   4.095   0.461  1.00  0.00           H  
HETATM   78  H41 UNL     1       8.834   4.404  -1.223  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3   41   42
CONECT    3    4   43   44
CONECT    4    5   45   46
CONECT    5    6   47   48
CONECT    6    7    8   49
CONECT    7   50
CONECT    8    9    9   51
CONECT    9   10   52
CONECT   10   11   11   53
CONECT   11   12   54
CONECT   12   13   13   55
CONECT   13   14   56
CONECT   14   15   15   57
CONECT   15   16   58
CONECT   16   17   18   59
CONECT   17   60
CONECT   18   19   20   61
CONECT   19   62
CONECT   20   21   63   64
CONECT   21   22   65   66
CONECT   22   23   67   68
CONECT   23   24   24   25
CONECT   25   26
CONECT   26   27   69   70
CONECT   27   28   34   71
CONECT   28   29   72   73
CONECT   29   30
CONECT   30   31   31   32   33
CONECT   32   74
CONECT   33   75
CONECT   34   35
CONECT   35   36   37   37
CONECT   36   76   77   78
END

HMDB0266526
     RDKit          3D
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0)
 78 77  0  0  0  0  0  0  0  0999 V2000
  -13.3594    0.4944   -1.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0014    0.1990   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3509   -0.9157   -1.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0670   -1.4769   -1.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8039   -0.7038   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8546    0.5153   -0.3581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.1803    0.0396    0.9689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6125    1.2489   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4093    0.7403   -0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3795    1.7112    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1209    1.4201    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174   -0.0208    0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5919   -0.3708    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2380   -0.7997    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4432    0.2784    1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302    0.3467    1.2978 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1142    0.9303    2.5914 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7809   -0.8811    1.2134 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2691   -1.8272    2.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1493   -0.4474    1.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7021    0.7302    1.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0489    1.2088    1.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691    0.2820    1.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -0.7358    0.4264 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4733    0.4518    1.6654 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121   -0.4617    1.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7860   -0.0704   -0.1985 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5002   -1.0723   -1.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8242   -1.3066   -0.7034 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3538   -2.4871   -1.8141 P   0  0  0  0  0  5  0  0  0  0  0  0
   10.8644   -2.1505   -3.2261 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0312   -2.6059   -1.8900 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6133   -3.9214   -1.3449 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3040    1.2391   -0.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5966    2.3786   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3480    3.6698   -0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4374    2.2565   -1.0200 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1679    1.3019   -2.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7653   -0.4191   -2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0205    0.9140   -0.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2490   -0.0357    0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5391    1.1879   -0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3208   -0.7398   -2.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1050   -1.7850   -1.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1618   -1.7937   -0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8600   -2.4591   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9600   -1.3356   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5106   -0.4717   -2.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5942    1.1975   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3572   -0.5078    1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7385    2.3590   -0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3216   -0.3071   -0.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5866    2.7920    0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    2.1664    0.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5006   -0.6954    0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9444   -1.6705    0.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709   -1.7128    0.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    1.2315    1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4067    1.0635    0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.4855    3.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982   -1.3353    0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406   -1.3494    3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8054   -1.3448    1.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0364   -0.1759    2.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0096    1.6103    1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318    0.5722   -0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2464    2.1705    0.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1132    1.4368    2.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3566   -0.2252    1.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1234   -1.4700    1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7537    0.0421   -0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9513   -2.0541   -0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3580   -0.7841   -2.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3684   -3.1075   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7689   -4.5986   -2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3868    3.4625   -0.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3238    4.0953    0.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8341    4.4036   -1.2234 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 27 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  2 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  6 49  1  6
  7 50  1  0
  8 51  1  0
  9 52  1  0
 10 53  1  0
 11 54  1  0
 12 55  1  0
 13 56  1  0
 14 57  1  0
 15 58  1  0
 16 59  1  6
 17 60  1  0
 18 61  1  6
 19 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  0
 22 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  6
 28 72  1  0
 28 73  1  0
 32 74  1  0
 33 75  1  0
 36 76  1  0
 36 77  1  0
 36 78  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(2R)-2-(Acetyloxy)-3-{[(5R,6R,7E,9E,11Z,15R)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoyl]oxy}propoxy]phosphonate	HMDB

Chemical Formula

C₂₅H₄₁O₁₁P

Average Molecular Weight

548.566

Monoisotopic Molecular Weight

548.238649138

IUPAC Name

[(2R)-2-(acetyloxy)-3-{[(5R,6R,7E,9E,11Z,13E,15R)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoyl]oxy}propoxy]phosphonic acid

Traditional Name

(2R)-2-(acetyloxy)-3-{[(5R,6R,7E,9E,11Z,13E,15R)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoyl]oxy}propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCC[C@@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@H](O)CCCCC)(COP(O)(O)=O)OC(C)=O

InChI Identifier

InChI=1S/C25H41O11P/c1-3-4-9-13-21(27)14-10-7-5-6-8-11-15-23(28)24(29)16-12-17-25(30)34-18-22(36-20(2)26)19-35-37(31,32)33/h5-8,10-11,14-15,21-24,27-29H,3-4,9,12-13,16-19H2,1-2H3,(H2,31,32,33)/b7-5-,8-6+,14-10+,15-11+/t21-,22-,23-,24-/m1/s1

InChI Key

PQQJZVSHZXSGAX-YLIDQWBLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1,2-diacylglycerol-3-phosphates

Alternative Parents

Substituents

1,2-diacylglycerol-3-phosphate
Monoalkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0266526)

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	2.65	ALOGPS
logP	2.19	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	141.39 m³·mol⁻¹	ChemAxon
Polarizability	57.98 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
AllCCS	[M+H]+	234.589	32859911
AllCCS	[M+H-H2O]+	233.072	32859911
AllCCS	[M+Na]+	236.361	32859911
AllCCS	[M+NH4]+	235.969	32859911
AllCCS	[M-H]-	229.277	32859911
AllCCS	[M+Na-2H]-	233.15	32859911
AllCCS	[M+HCOO]-	237.542	32859911
DeepCCS	[M+H]+	217.411	30932474
DeepCCS	[M-H]-	215.016	30932474
DeepCCS	[M-2H]-	248.049	30932474
DeepCCS	[M+Na]+	223.3	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0)	[H][C@@](COC(=O)CCC[C@@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@H](O)CCCCC)(COP(O)(O)=O)OC(C)=O	5355.2	Standard polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0)	[H][C@@](COC(=O)CCC[C@@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@H](O)CCCCC)(COP(O)(O)=O)OC(C)=O	3456.7	Standard non polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0)	[H][C@@](COC(=O)CCC[C@@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@H](O)CCCCC)(COP(O)(O)=O)OC(C)=O	4224.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #1	CCCCC[C@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C)O[Si](C)(C)C	4236.1	Semi standard non polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #1	CCCCC[C@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C)O[Si](C)(C)C	3579.6	Standard non polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #1	CCCCC[C@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C)O[Si](C)(C)C	4781.9	Standard polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #2	CCCCC[C@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C)O[Si](C)(C)C	4211.1	Semi standard non polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #2	CCCCC[C@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C)O[Si](C)(C)C	3622.0	Standard non polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #2	CCCCC[C@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C)O[Si](C)(C)C	4637.2	Standard polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #3	CCCCC[C@@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C	4211.5	Semi standard non polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #3	CCCCC[C@@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C	3615.2	Standard non polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #3	CCCCC[C@@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C	4631.8	Standard polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #4	CCCCC[C@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](O)CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C	4227.8	Semi standard non polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #4	CCCCC[C@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](O)CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C	3591.4	Standard non polar	33892256
PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0),4TMS,isomer #4	CCCCC[C@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](O)CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(C)=O)O[Si](C)(C)C	4649.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	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 - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) 10V, Negative-QTOF	splash10-0002-0000090000-051bd336b944e42fcb33	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) 20V, Negative-QTOF	splash10-0k9b-6615790000-ded4c3074026acf56c87	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) 40V, Negative-QTOF	splash10-0zfr-7319130000-3384758e2918b1aae78a	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) 10V, Positive-QTOF	splash10-001j-0000090000-13f37ed029974d9bd643	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) 20V, Positive-QTOF	splash10-0f6t-0000590000-2b22078059934b8d8634	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) 40V, Positive-QTOF	splash10-0uds-0300910000-cc836df9fde399a451de	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) 10V, Positive-QTOF	splash10-00di-0000090000-574813b40334623480d5	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) 20V, Positive-QTOF	splash10-00di-0000990000-330c25a533ef17e4c2a7	2021-09-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) 40V, Positive-QTOF	splash10-02mi-0050290000-f5e610432832fb458a08	2021-09-28	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156969878

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

Hajeyah AA, Griffiths WJ, Wang Y, Finch AJ, O'Donnell VB: The Biosynthesis of Enzymatically Oxidized Lipids. Front Endocrinol (Lausanne). 2020 Nov 19;11:591819. doi: 10.3389/fendo.2020.591819. eCollection 2020. [PubMed:33329396 ]

Only showing the first 10 proteins. There are 61 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Phospholipase D2

General function:: Involved in protein binding
Specific function:: May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:: PLD2
Uniprot ID:: O14939
Molecular weight:: 104656.485

Enzyme Details

2. Diacylglycerol kinase theta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Phosphorylates diacylglycerol (DAG) to generate phosphatidic acid (PA). May regulate the activity of protein kinase C by controlling the balance between these two signaling lipids. Activated in the nucleus in response to alpha-thrombin and nerve growth factor. May be involved in cAMP- induced activation of NR5A1 and subsequent steroidogenic gene transcription by delivering PA as ligand for NR5A1. Acts synergistically with NR5A1 on CYP17 transcriptional activity
Gene Name:: DGKQ
Uniprot ID:: P52824
Molecular weight:: 101154.0

Enzyme Details

3. Diacylglycerol kinase gamma

General function:: Involved in diacylglycerol kinase activity
Specific function:: Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:: DGKG
Uniprot ID:: P49619
Molecular weight:: 89095.3

Enzyme Details

4. Lipid phosphate phosphohydrolase 2

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:: PPAP2C
Uniprot ID:: O43688
Molecular weight:: 32573.435

Enzyme Details

5. Diacylglycerol kinase alpha

General function:: Involved in diacylglycerol kinase activity
Specific function:: Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:: DGKA
Uniprot ID:: P23743
Molecular weight:: 82629.5

Enzyme Details

6. Diacylglycerol kinase delta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:: DGKD
Uniprot ID:: Q16760
Molecular weight:: 134524.2

Enzyme Details

7. Lipid phosphate phosphohydrolase 1

General function:: Involved in catalytic activity
Specific function:: Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:: PPAP2A
Uniprot ID:: O14494
Molecular weight:: 32155.715

Enzyme Details

8. Diacylglycerol kinase beta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:: DGKB
Uniprot ID:: Q9Y6T7
Molecular weight:: 90594.7

Enzyme Details

9. Diacylglycerol kinase iota

General function:: Involved in diacylglycerol kinase activity
Specific function:: ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl- sn-glycerol 3-phosphate
Gene Name:: DGKI
Uniprot ID:: O75912
Molecular weight:: 116996.2

Enzyme Details

10. Lipid phosphate phosphohydrolase 3

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:: PPAP2B
Uniprot ID:: O14495
Molecular weight:: 35115.61

Only showing the first 10 proteins. There are 61 proteins in total.

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Showing metabocard for PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0) (HMDB0266526)

MOL for HMDB0266526 (PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0))

3D MOL for HMDB0266526 (PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0))

3D SDF for HMDB0266526 (PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0))

3D-SDF for HMDB0266526 (PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0))

PDB for HMDB0266526 (PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0))

3D PDB for HMDB0266526 (PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0))

SMILES for HMDB0266526 (PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0))

INCHI for HMDB0266526 (PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0))

Structure for HMDB0266526 (PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0))

3D Structure for HMDB0266526 (PA(20:4(7E,9E,11Z,13E)-3OH(5S,6R,15S)/2:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes